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What if you could regularly have sex with young, beautiful women with nearly no chance of rejection? Would you do it?

Well, you can. Right now, in fact. This isn’t a joke or a scam.

You just have to become a sugar daddy.

For those who don’t know, there are sites dedicated to grey-area paid arrangements. The most popular is Seeking Arrangement.

Basically, you pick a gorgeous girl (a sugar baby) from her online profile. You negotiate an allowance or pricing structure, and if agreed upon — you go on “dates”. Then somehow like magic…you also have the option of sleeping with that woman.

Of course, you do need the means to pay for this. But really, it’s often cheaper than you’d expect.

Depending on your location, you can find women who will sleep with you every week for about $1000-2000 per month. And I’ve heard from guys that have paid much less — sometimes just for a nice dinner. It’s an investment but a lot of smart, single men I know can afford that if they budget for it.

This is the dream for many guys: no-strings attached sex where you live out your wildest kinks and fantasies. I’ve found that it appeals most to young men with little romantic experience and older men coming out of a long-term relationship.

(I know a lot of married men use this as well but I’m going to focus on single guys since that’s who I work with.)

So what’s the catch?

Well…there’s a significant hidden cost. And it usually comes in the form of your self-worth and long-term happiness.

This isn’t me preaching some moral high ground. I’m all for legalized, safe regulation of the world’s oldest profession.

I’m just telling you how things generally unfold in these situations. I’ve talked to a lot of men who were excited about being a sugar daddy only for them to end up feeling worse about themselves and regretting the whole experience.

Why single men THINK they become sugar daddies

The problem starts with most men’s mindsets going into these arrangements. They often tell themselves (and honestly believe) they just want some casual fun.

They feel like they need to get laid to get out of their rut. They want to discreetly explore their fetishes. They want sex and companionship without having to deal with a relationship.

For those reasons, the sugar daddy business is ideal! (Or so they thought.)

So they end up dating a bunch of sugar babies who give them attention. They live out their sexual desires. They even travel for exciting adventures with these women.

But at some point, the dream begins to lose its luster. Like too much of anything, the novelty of new, random sex wears off. The men lose the drive to keep sleeping around aimlessly because they start feeling something is missing.

THAT’S when they’re faced with the deeper truth: they didn’t get into this just for the sex.

Why those men REALLY become sugar daddies

In theory, these successful men should’ve been able to organically attract beautiful women.

With just the money they invested in sugar babies, they could have invested in making themselves more attractive.

They could have fixed their teeth or eye sight. They could’ve hired a fitness or dating coach. They could’ve gotten stylish haircuts and bought custom-fitted clothes. Then they could’ve had professional photos taken for online dating.

And even THEN, they’d still have money to take real women out on incredible dates! Combine that with a little exposure and practice in the real world — and they should have their choice of great women.

But they didn’t go that route and if they could have, they would have. Instead, they endlessly struggled with social anxiety, fear, motivation, or countless lost romantic opportunities.

And after rejection, loneliness, and emotional starvation…

They took the easy road. They ran away and ignored their problems. And to protect themselves, they convinced themselves they just wanted the sugar daddy lifestyle.

The thing is, eventually our true needs get the best of us. These guys start to crave the things we all need in our lives: real affection, adoration, loyalty, meaningful connection, and even love.

This is where the downfall starts. These men realize that even with all the money in the world, they still can’t buy what we really want in life.

The sugar lifestyle doesn’t build real connections

Over time as a sugar daddy, it becomes harder to ignore the underlying business dynamic. It becomes apparent these sugar babies view the relationship as transactional.

Yes, these women may like their clients as a person. They can enjoy their company. They even sometimes find the men physically attractive.

But at the end of the day, the chance these women see a client as the man they truly desire, long-term, is slim to none.

Because the man of their dreams is someone they naturally fall for. They want a high-quality man they find attractive for his personality and confidence. They want to see him as a “catch”.

Being a sugar daddy does the exact opposite. It reinforces that you need to pay for these connections. That you can’t get them yourself. That what you feel you have to offer is your money and not who you are.

This will never provide the deeper emotional connection needed for a lasting relationship. These women may think you’re a great guy in their mind, but in their heart, they feel otherwise.

Sugar babies can’t hide their feelings forever. Even the most practiced women will subtly reveal the truth with their actions.

So the dream turns into a nightmare

It feels horrible when you never get this look from her.

Some guys see the mirage fade over time.

They notice a woman force enthusiasm or engagement. They see that this beautiful woman isn’t fully aroused and invested in sex. They don’t see the authentic passion in her eyes when she looks at them.

They are reminded of the business relationship when simple dating rituals get negotiated for more money: spending the night, eating breakfast together, or going away for the weekend.

Then they feel devastated when they see how easy it is for one of these women to leave for another arrangement. Or, when they find out she actually has a man she’s legitimately interested in.

Some guys see the mirage disappear all at once.

They date one of these women for a long time and feel like they have a shot at a deeper connection.

And when they try to turn it into a real relationship, the woman is forced to reject them. She has to break the news that she doesn’t see him like that and wants to keep things the way they are.

Whether it happens slowly or all at once, sugar daddies end up feeling worthless, powerless, and alone. The thrill of sex can’t overpower their other emotions any longer. And this is where they leave the sugar daddy lifestyle.

Then comes the overwhelming regret and shame

Unfortunately, at that point the damage is already done. These men feel worse coming out of the experience. Because once the thrill is gone, all that’s left is regret.

That regret turns to shame. Shame that they resorted to this and that they deluded themselves into thinking it meant more. Shame that they ignored all the red flags from the sugar babies.

Because of the nature of the business, some of these women aren’t in an emotionally healthy place. They may not even want to be doing it, but have to because of their financial situation.

This puts men in a tough spot because they have to accept the (sometimes sad) reality that put the women on the market in the first place. And it makes them feel like scumbags who took advantage of the situation.

I’ve seen that shit haunt men for years. They become disgusted with themselves for their lack of empathy and seek therapy to reconcile their actions. Then they struggle with future women because they’re weighed down by their guilt.

How to be a sugar daddy without hating yourself

This is the dark path many sugar men walk. It doesn’t have to end up like this!

Like I said, I’m not against these types of arrangements. We all have needs. And I believe two consenting adults should do as they please.

But if you’re committed to indulging in this lifestyle, you need to have the right expectations and mindset.

1. Don’t expect more than a transactional deal. That doesn’t mean you’re a cold-hearted asshole. It means accepting that this is her profession and treating her like a professional. When your encounters are done, they’re done. If you’re looking for real companionship or love — look elsewhere.

Have men married sugar babies and turned them into trophy wives? Sure. But it’s rare and I’ve yet to meet an actually happy couple in those situations. Because again, those women are settling for convenience and logic, not a meaningful emotional connection.

This is why many of these relationships turn into sexless marriages. Over time, you both never feel fully satisfied and one of you will try to get those needs met: by cheating or leaving.

2. Stop using this to compensate for what your romantic life is missing. These types of deals are for fun flings. They could be for a quick hookup when you’re traveling or too busy with a big project. Or to supplement your existing dating life with something different or uncomplicated for the time being.

3. Use this in balance and moderation. If you invest in paid women, you should also invest in improving yourself and your ability to create organic connections. Because again, these experiences are unlikely to fulfill you on any meaningful level or provide a real partner. You’re just delaying your happiness.

And in general, use sugar daddy sites sparingly. When we overindulge in something, we often become dependent on it. Then it becomes easy to forgo your real personal development.

4. Treat these women with respect. They are like any other human being. They’re not sex objects to manipulate or control. If a woman doesn’t want to do something, don’t pressure her or guilt her into it. Pay her a fair wage for her services. Stop trying to prevent her from seeing other men. Don’t expect extra attention or time just because you’re nice to her.

If you know you did your best to provide a positive, honest experience for both of you — everyone wins. And then you’ll have nothing to feel wrong about.

Don’t sour the sweet experience.

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Let me ask you…

When you’re really sick, who do you want by your side?

When I was young, I often got mind-numbingly painful migraines. In those moments, I wanted nothing more than my mom to sit by my bed and massage my forehead until it felt better.

When I was in my early 20s, I got a terrible case of swine flu. At that time, I just wanted to be left alone which then made me realize the girl I was dating probably wasn’t the one for me.

Now in my early 30s, I’ve had to be admitted to the hospital for severe dehydration after a bad reaction to anesthesia. What made me feel better was having my wife right by my side.

When you’ve come face-to-face with death, what really matters?

When I was 21 years old, I was racing another car down I-95 south of Boston in the rain. As I rounded a curve, I faced dead-stop traffic going well over the speed limit. I had no time to slow down and plowed into the car in front of me and my car flipped through the air.

Then my car wrapped around an enormous tree in someone’s backyard and smashed into their fence. Every area of the car was destroyed — except for my driver’s seat.

Thankfully, no one else was injured by my foolish and irresponsible driving.

So what was I thinking as I was gliding through the air, facing certain death? What did I think when I stepped out and had to figure out what to do next?

I felt an overwhelming wave of contempt for the unethical people I worked for. This led to me quitting that job and pursuing what I do today, full-time.

Neil Strauss is the famous author of the book, The Game. In the sequel, The Truth, he writes about his struggle with love addiction and finding fulfillment.

At the end of the book, he talks about how he almost died at the top of a mountain. And it was that moment that finally made him realize that he wanted to fully commit to one woman, who is now his wife. Let’s just say I was crying on my long flight home after reading that one.

If you’ve had similarly intense experiences, you’ve also probably gained some life-altering insight.

Because I’ve found that somehow in those overwhelming moments of misery when you shouldn’t be able to think straight, you find perfect clarity.

That’s why I believe that the acceptance (or at least the awareness) of death can help us prioritize what matters — the relationships we have.

How can you use tragedy to gain clarity?

Without tragedy, I don’t think we truly understand the importance of our relationships. We don’t fully accept how fragile and fleeting they really are. We don’t feel a sense of urgency to invest in those connections.

And I want that to change.

So in lieu of suffering through real-life traumatic events, I just want you to use your imagination. (This is a variation of an exercise suggested by my colleague, Jason.)

Close your eyes and picture yourself sick on your deathbed…

Who do you wish was there holding your hand? Whose energy in the room would bring you a sense of calm and relief? Who would you miss deeply if they stepped out of the room?

Really put yourself there and try to feel the weight of the emotional weight of these experiences — even for just a couple minutes.

Who are you thinking of? It could just be one or two people.

Maybe it’s your partner. Or your childhood best friend or college buddy. Maybe it’s your kids.

This is who really matters.

(Note: If this exercise doesn’t work for you, imagine someone else you know on their deathbed. Who you want to be with in their final moments?)

How do you spend quality time with the people you love?

I want you to reach out to those people right now, today. Not tomorrow or later this week. It takes a few seconds to send a text and start a communication channel.

Then I want you to make plans to spend quality time together, face-to-face.

Even if they are far away, you can start with a phone call right now to plan out when you’re going to take a future trip to see each other.

Then put these plans somewhere concrete, like in your phone calendar. Send a calendar invite to the other person if you have to. Set extra reminders to go off for yourself.

Then commit to seeing them.

When you do see that person you care about, remember that you’re supposed to spend QUALITY time with them.

That means you’re fully present and not half-checked out. That means having a real date night with your wife where you actually sit together and have a conversation — not hang out at the dinner table independently on your phones.

Quality time means deepening the connection with that person by showing them a real part of you that they haven’t seen before. Or really digging into what’s been going on in their lives and how they’re feeling.

In life’s toughest moments, we realize people are our solace. But please don’t wait until you’re sick or near-death to start cherishing those relationships.

I’ve watched a lot of people I know get sick or pass away in the last few years. Those experiences make it crystal fucking clear what really matters most.

Because you can always stream that show later. You can always read that article tomorrow. You can always get back to your social media feed.

You know what you can’t get back? The time you wished you spent with someone special.

I’ve definitely regretted the times where I binged a TV series or put dozens of hours into a game. But I’ve never regretted spending quality time with the people I care about. Not once.

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Don’t. Get. Married.

You’ll lose your freedom. You won’t see your friends. Worst of all, say goodbye to your sex life.

That’s what people told me my whole life. And like many guys, it made me terrified of commitment.

I knew that 40-50% of marriages ended in divorce. My parents split by the time I was seven years old. Then my mom got divorced again after her second try.

As I got older, friends and co-workers told me horror stories about how bad their serious relationships were. So I never wanted to get into a long-term relationship, let alone a marriage, because that path seemed to only lead to misery.

I know many of you, men and women, have heard this, too. You may even feel the same way.

And truthfully, serious relationships aren’t for everyone. I know many happy people who only date casually or remain single by choice.

But I think relationships and marriage have gotten an unfairly bad rap.

Many people are in fulfilling relationships and genuinely in love with their partners. I’m fortunate to be one of them.

It’s not easy, though. You have to work hard at it all the time. You have to push your comfort zone, challenge your emotions, and get through some real pain.

But it can also be life-changing, fun work with your best friend. You get to be an amazing team that grows together.

And what I’ve realized after years of coaching people in their love lives is…

A lot of the people shit-talking relationships are the ones responsible for their own misery. And they’re just projecting that unhappiness onto you.

Here are three common reasons why your friends might be unhappy and how you can avoid the same pitfalls.

They chose an incompatible partner

You don’t need to date someone just like you. But there are certain fundamental values that can make or break a future relationship.

These include things like having kids (and how many), religious practices, political views, sex drive or attitude towards sexuality, and where you want to live.

You either have to find someone who aligns with your values or you both have to truly accept each other’s differences. You can’t hold resentment or secretly want to change the person.

Many people who complain about their relationship overlooked this. They didn’t want to have those hard discussions with their partners. They believed they could ignore the issues or deal with them later.

Or sometimes, they just settled. Maybe out of fear that they wouldn’t find someone better or out of desperation because they felt time was running out.

This is why I think it’s important to date around at some point in life. See the types of people that are out there. It can help you better understand yourself and understand who’s compatible with you.

If you get into a long-term relationship, you will spend more time with this person than with anyone else. Do you know how fucking hard it is to be around anyone that much?

And if you’re getting married, it will be one of the biggest decisions you’ll ever make. Finding the right person should be a tough, informed choice.

The truth is, many people don’t put in that required upfront effort. Then they pay the consequences for years to come.

They chose someone who didn’t respect them

People often say things like, “communication” or “compromise” are the most important parts of a relationship. Yes, they’re important, but they fall under the umbrella of something bigger: respect.

I believe deep mutual respect is at the core of every healthy relationship.

That idea goes much deeper than people realize. It’s not only about treating the other person with kindness. It’s about caring so much for them that you will do whatever’s necessary to build a relationship that makes both of you happy.

People ignore disrespect or justify to themselves why it’s okay. I can’t go a week without some guy asking me how to convince an emotionally unavailable woman to like them.

My answer is always, “You don’t. Stop chasing those women and find someone who’s just as excited as you are.”

The people who choose not to listen to that advice are usually the same ones struggling with aloof, manipulative partners. Then they boldly declare relationships are doomed.

(Note: I understand some people are unlucky. They chose a seemingly healthy partner who changed for the worse. I’m not talking about them.)

A lack of respect can be more subtle than the traditional forms of emotional and physical abuse. But it’s destructive all the same. Some early warning signs I’ve seen people overlook in a partner include:

  • They consistently cancelled on plans without notice and rarely apologized. They also didn’t change their future actions.
  • They shut down or stonewalled during difficult conversations. They went randomly cold on communication, especially as a tactic.
  • They tried to stop their partners from seeing friends or having independence. They may have even gaslighted or threatened them. They didn’t support the pursuit of hobbies or passions outside the relationship.
  • They used sex or intimacy as a weapon. Or they avoided intimacy and were unwilling to address the subject, even when their partner tried to talk to them.
  • They regularly put their significant other down or talked down to them in front of people. Yes, even if they claimed they were “joking”.
  • They expected the other person to pay for everything. They used guilt-tripping or the cold shoulder when they didn’t get their way.

These are just a few examples. You can reference more here and here.

These toxic relationships are never worth it and they never work out.

If someone can’t respect you during the early stages when you’re supposed to be obsessed with each other, it’s only going to get worse.

They didn’t (and still don’t) respect themselves

Show yourself some respect.

In order to earn respect, you must also have self-respect. That means knowing what you need in a relationship to be happy and being willing to communicate that.

Many people complain about problems with partners as if they’re helpless victims.

But when you dig deeper, you often discover that they never set their expectations at the start of the relationship. And they still don’t set their boundaries now. They avoid telling their partner what they feel is missing or what they need more of. 

Then they resent and even blame their partners for not fixing their problems.

Because of their self-inflicted suffering, they feel stuck in situations where:

  • They don’t have the sex life they want. They don’t have the frequency or type of sex they desire. They feel trapped in monogamy when they never wanted that.
  • They don’t have personal freedom. They feel obligated to spend all their time with their partner. They may feel like their partner is overly dependent on them. 
  • They can’t be themselves. They initially hid their personality out of fear of being judged or rejected. They did whatever activities they thought their partner wanted to please them. Now they feel they can’t let loose and express themselves. They worry if they do, their partner will feel blindsided or misled.
  • They pull most of the weight. They organized everything, paid for everything, and took charge of all the responsibilities. Now they feel they can’t ask their partner to contribute without seeming weak or unreasonable.

I understand that these conversations can be fucking uncomfortable. 

Especially ones like discussing sex outside the relationship. For example, you want to add partners to the bedroom, swing, or have an open relationship.

But what’s the alternative? Be unfulfilled and miserable ever after?

In that scenario, the only alternative is infidelity and I’ve watched that destroy so many lives.

That’s why the best time to start respecting yourself is from the beginning stages of dating. Own your hobbies, interests, passions, limitations, and everything in between.

You will show other people that you’re a confident, self-respecting individual. It’s their job to decide whether or not they want this type of relationship (or find a compromise).

This only makes people who are serious about you want to work harder for you. And it weeds out the people who aren’t planning on investing back in you.

Don’t wait to communicate your self-respect. It sets the tone that you want a relationship that will grow and evolve. It’s so much harder to try and do this years later.

Yes, all this is what it takes to create a sustainable, fulfilling relationship.

It works both ways, too — you can’t just do all this for yourself. You also have to let your partner express their needs, respect them, and find compromises that satisfy everyone.

Like I said, serious relationships aren’t easy. But if done well, the reward is worth it: you get to grow and share an amazing life with your best friend.

My relationship isn’t perfect. It has tough moments. And I never know what the future will hold.

I wouldn’t trade it for anything, though. The days together are better than the days alone. And I truly believe the whole can be greater than the sum of its parts.

Don’t just listen to all the haters — be open to a great relationship. Then evaluate whether or not it’s for you.

Because if you picked the right partner and can find respect for each other, you’d never talk bad about something so beautiful.

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The spoken word carries immense power.

A person’s voice can start revolutions. It can captivate audiences. It can make someone fall in love.

In the same sense, restricting a voice can have devastating consequences. Even when the person restricting it is yourself.

I bet there are so many things you wish you could say to other people.

You want to tell a woman that you find her attractive. You want to have a hard conversation with your parents. You want to tell your boss a new idea.

In the moment, though, having these conversations feels overwhelming and impossible. You think you’ll sound stupid or weird. You’re worried about how you’ll be judged.

So you only ever think about what you want to say without ever saying it out loud.

And by doing this, you never gain the experience necessary to get more confident with expressing yourself.

But what if you had a completely SAFE way to start saying the ideas you’ve held back? Could it help you overcome your social anxiety?

I’ve been trying a new technique with clients lately and the results have been astounding…so I want to share it with you today.

How do you practice when even easy mode is too hard?

Many men struggle with introducing themselves to women they find attractive. So I try to make it as easy and low-pressure as possible for them to get started.

I don’t want them focusing on “cool” lines or reading a woman’s mind to figure out what she wants to hear. That only creates more anxiety.

Instead, I first teach men to be more present in social environments. From there, I want them to try and connect with their opinions, observations, feelings, and natural curiosity about the environment and the people around them. Just quick thoughts like, “How does she journal in the park with so many people around?”

These simple ideas are all you need for a great introduction.

Then, they can practice with less intimidating people in safe environments. Such as…

Telling a barista how much they love their coffee shop. Asking someone if they can pet their dog. Sharing an observation with a classmate after a yoga class.

The problem is, sometimes even THIS is too difficult for the men I work with.

They never give themselves permission to say anything and their real-world practice stays at zero.

I knew I had to create another small step that would lay the foundation for them to express themselves more freely.

That’s when I thought about my own struggles with public speaking.

My eureka moment: think like a professional speaker

When it comes to talking to strangers, I’ve had years of experience that have now made me comfortable with it.

When it comes to public speaking, though, only recently have I mastered my anxiety.

I host retreats that involve a LOT of talking from me. Before my first retreat, I felt a ton of pressure to be the best speaker possible for the attendees. I had to not only teach but also engage them for eight hours a day, for five days straight.

My friend Jason, a former professional speaker, told me to try rehearsing out loud. He said to just vocalize my thoughts to myself. Eventually, I could try doing it in the mirror or record it for later playback.

The first time I tried to do this, I felt huge internal resistance. I doubted myself and I felt really awkward.

But because I didn’t have anyone around to judge me, I was able to speak up. And that’s when amazing things started happening.

I realized that it wasn’t as bad as I’d imagined. Within a couple of takes, I started sounding better and getting my words out more clearly. I felt like I could gather my thoughts. As my anxiety subsided, I got looser and had more fun with it.

Soon enough, I felt like I had delivered my speech to a real group of people.

My brain didn’t know the difference. I was still overcoming my anxiety and speaking up in the moment. That self-practice made me feel more confident that I could do it and actually show up when I needed to.

Solo practice is key to speaking up when you’re not alone

As I said, I’ve been using this approach to great effect with clients. I recently worked with a guy who couldn’t give a genuine compliment about what he found attractive in a woman.

My coaching partner Kristina and I created a “compliment vocalization” plan:

  • We showed him pictures of attractive women smiling into the camera. We asked him to find something he liked about them and say it out loud. He was so nervous he couldn’t speak for 20 seconds and his voice trembled. We did this several times until he got more comfortable.
  • Then while we were out walking around and saw someone he was interested in, he had to tell us what he found attractive about them.
  • Then we made him look at those women (when they weren’t looking at him) and say his compliment out loud as if he was saying it to them. We did this when no one else was close by.

And what happened next?

Later that day while on a stroll through the city, we looked back to see that he’d walked over to a woman, gave her a genuine compliment, and caught back up with us.

He did this all on his own, UNPROMPTED.

The previous practice made him feel like he’d already lived through that experience before and gave him the courage to take the shot.

Later on, we all ended up talking to a girl together. Ten minutes into the conversation, he gave her a direct compliment, to which she blushed and kind of brushed off shyly. He looked into her eyes and repeated it sincerely, and she excitedly accepted.

She ended up coming out to see him twice more while we were visiting the city.

He went from feeling like he could NEVER give an attractive woman a compliment to doing it unconsciously with only a couple hours of practice.

Learn to trust in the sound of your own voice

Take this vocalization technique and apply it to the things you have difficulty saying to others and yourself.

Let’s say you struggle to…

Talk about your sexual inexperience. Many guys avoid getting onto certain subjects or moving dates forward romantically because they don’t have much experience. Sometimes, they avoid dates altogether because of it. 

But your sexual inexperience isn’t a problem, you just need to talk about it in a way that shows you’re comfortable with yourself.

Again, look at a photo of someone you’re attracted to or are already dating. Imagine they just asked you about your past relationships. Practice one of two options: tell them that you never met the right person and didn’t want to sleep with someone you didn’t feel connected to. OR politely tell them you don’t want to talk about your dating past with a new person and would be open to sharing it if you two became closer. Reference my article on discussing your sexual past.

Show yourself love or gratitude. Look at yourself in the mirror and sincerely tell yourself, “I love you.” Or try saying something you’re proud you did that day or week, “I’m grateful that I signed up for that photography class because it means I’m pushing myself to get out more.” Being compassionate and recognizing what’s awesome about you builds lasting self-esteem. Read more about gratitude and the power of positive psychology here.

Give compliments to women you find attractive. Pull up some photos of women you find attractive on social media. Find something you genuinely like about them: that could be their style, smile, or eyes. Clearly state that you like that quality in them, “Your eyes are stunning, I’m getting lost in them.”

You can then practice this while out in the real world from a safe distance. When you see someone you like, say a compliment about them out loud to yourself. Next, while looking at them, really imagine yourself saying it to them as you speak the words.

Obviously, you don’t want to just compliment women on their looks. Compliments on personality tend to be much stronger. But this is just easy practice to get comfortable showing romantic interest. Reference how to give good compliments here.

Introduce yourself to a new person. Look at my advice earlier in this article and in this post. Start by just being present in social environments and having a lot you want to comment on or ask about. Focus on what YOU experience from your senses rather than what you believe people will want to hear. You can even journal these thoughts in your phone in the moment or after you go home.

Once you start to naturally have a lot to say, look at someone that’s far enough away that they can’t hear you. While looking at them, casually share one statement or question in a clear voice. (You can have your AirPods in if you’re worried about talking to yourself.)

This exercise is ESPECIALLY important to practice as often as possible. This is because you’ll sometimes have only a few seconds to say something to someone near you. You want to get to the point where shareable ideas pop into your head without consciously thinking about them.

Tell your boss you have a new or different idea. Visualize yourself in a 1-on-1 or group meeting with your boss. You can even reference a real moment when you had an idea that you didn’t share. Say it out loud starting with a positive I: “I think the team is doing a great job with X but I think we could improve when it comes to Y…” Do this after a bunch of meetings or whenever you have the urge to contribute something different.

Speak up to your parents. Having hard conversations with your parents is one of the toughest yet personally rewarding things you can do. I had to tell my own folks about leaving a cushy career to start this business and I also had to convince them to quit smoking.

Use a picture of your parents or an object to represent them. Take your time and try to express your feelings openly. Some of the best psychiatrists who specialize in healing trauma advocate this, like in the book The Body Keeps the Score.

If that still feels challenging, you can try writing it out as if you were going to send them an email to formulate your thoughts better. Then take that writing and read it out loud to those inanimate objects.

Share a hobby or opinion you’re embarrassed about. A lot of shame around our hobbies or opinions start because we feel people will perceive them as stupid, weird, or boring. But if you share something with passion and in a way people can understand, anything can be deeply engaging.

Write down why you love a hobby or why you feel a certain way about a subject. Flesh out WHY it’s important to you. Jot down how it makes you feel. If it’s something technical, write out how you could explain it simply and relate it in a way other people could understand.

When you fully understand why you connect with this, it will be easier to have others feel the same way, too. Gather your thoughts and practice talking about it for a minute out loud.

Tell a woman you’re not ready for an exclusive relationship. Many women will be open and accepting of dating you casually if they know it’s coming from a healthy place. It’s when you poorly communicate, “I just still want to date around…” that makes women fear you’re just using them and don’t care about them.

Look at a picture on your phone of a woman you’re dating, preferably one you took together so you feel connected to it. Explain out loud how you care about her but maybe have rushed into things in the past or you just want to make sure you two are right together so no one gets hurt. Reference how to do this gracefully using this article.


As a reminder, all of these can first be practiced alone, at home. You can reflect on someone you recently encountered and say what you wished you’d said. Or you can use an inanimate object to represent a person while you practice speaking to them.

Next, try doing this in a social space. Really look at the people you want to share something with, and under your breath or where no one can hear you, say it as if you were really talking to them.

Do this as often as it takes to get more comfortable. Practice makes perfect...even if it feels ridiculous right now.

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Men get hung up when they need to follow-up with women.

When it’s time to message a girl they recently met, just had a date with, or haven’t talked to in a while – they panic.

They tell me they totally blank on what to say next. They want to write a perfect, charming message but it feels impossible when there’s hardly any context to build from.

So they overthink it because they don’t want to say the wrong thing. They second-guess their ideas and delete draft after draft. They stress themselves out and hate every minute of it.

And in the pursuit of that perfect message, they often procrastinate. Sometimes, they procrastinate so much that they lose out on opportunities and self-sabotage.

Ironically, when these guys do finally send out a message they worked so hard on…

It’s garbage.

It’s generic. It feels cold. It’s bland and evokes no emotion. It’s completely safe.

And it makes it even more obvious to a woman that you two are strangers who lack rapport.

It’s often some variation of, “Hi Allie, this is Nick from X. It was great meeting you.” Or “Hey, how was your weekend?” Or “I had a fun time the other night. Hope you got home okay.” Or “Good morning, hope you have a great day!”

Do you really think this is how women want to reconnect with a guy they’re supposed to like?

Set the right tone from the start

In early courtship, you’re supposed to be so fucking excited about getting to know each other. A girl wants to feel like you two already have a vibe: some special chemistry, something unique.

She doesn’t want to hear the same exact thing she’s heard from every other guy.

Sure, you can start off with these basic messages and segue into more interesting conversations – but you’re working from a weak foundation.

When you play it safe, you’re setting a detached, “we-don’t-know-each-other” tone. This tone is then hard to break out of and you’re stuck in a cordial, factual dialogue. Zero personality and zero passion.

By doing this, you also don’t give a woman much to work with. You’re not inspiring her to get more personal and open up with you. You’re not making her feel comfortable to let loose and be herself.

So how are you supposed set the right tone?

The answer is in the definition of the term “follow-up” itself…

“A continuation or repetition of something that has already been started or done.”

You need to pretend as though you already have an existing connection.

It’s up to you to take the lead and just continue the conversation as if you’ve known each other for a while.

Guys in this situation hold back and feel like they need to slowly feel her out. They think it’s weird to bypass the initial boring small talk. Then their messages sound impersonal because they don’t dig a little deeper and really put themselves out there.

But don’t forget – you’ve ALREADY met and chatted. So trust that you can now roll into meaningful, weird, goofy, or playful banter just like you would with an existing friend.

Take the leap and believe that if you act like you know each other, you will feel like you know each other.

3 ways to follow up like you already know each other

Here are three ways to follow up so it feels like you’re continuing a natural connection.

Build off your previous discussion

Imagine yourself back into your last conversation. Think…

What did you talk about? What did you laugh about? What did you unexpectedly learn about her? What do you want to know more about from what you learned? What did she tell you she was planning to do?

For example…

  • Talk about the show she said she was going to. “Was the show everything you wanted it to be?” or “Please tell me you got on stage and took over the whole concert with that positivity energy of yours.”
  • Call back to a joke you two had. “I’ve almost got those sweet dance moves down I learned from the guy on the sidewalk last night.”
  • Share your further reflections on something you discussed together. Maybe she talked about a recent trip so you say, “So tell me about the people in Ecuador. What were they like?” or “You know what, I do think I’d go to Mars IF they got decent internet up there. I can’t miss the new season of Game of Thrones.”
  • Dig deeper into something she told you about herself. “When did you decide teaching little monsters was your passion?” or “So what is it about photographing models that’s so fascinating? (Besides getting to look at hot models all day)”
Or keep sharing yourself with her

Basically, let her know what you’ve been up to or what’s on your mind. Think…

What experience did I have that I want to tell or show her about? What am I really excited to do today/tomorrow/soon? What interesting experience did I have today? What did I just discover that I love?

For example…

  • Share an interesting moment or experience you just had. “I just saw this old couple giggling and being playful with each other like kids. That’s what I call winning at life.” or “Have you been axe throwing? It sounds ridiculous but I may have found a new favorite hobby.” Or send her a photo from the top of the hiking trail looking over the lake, “I could’ve sat here all day.”
  • Tell her about something fascinating you just read, watched, or listened to. “I just watched Netflix’s Sex Education. My high school experience was not like that at all haha.” or “Have you heard about that Zombie Deer disease? Shit…this is how the apocalypse starts.” or “Damn, Paul McCartney’s new album is FIRE. It’s almost as if he’s a legendary rock star or something.”
  • Tell her about somewhere you’ve got planned to visit and are pumped about. “Wish me luck — going to my first drag show to support a friend who’s in it. He actually looks fabulous.” or “I hope you’ll still want to talk to me after I gain 20lbs of paella in Spain.”
  • Send a picture of you and your pet being cute together. “No, he’s not for sale but you can get some free pets and snuggles.” or “7 years old and still acts like a big baby.”
  • Ask her opinion or help for a situation you’re in. “What would you do if your friend just starting dating a new guy and he gave her a $7,000 Cartier bracelet?” or “Would you judge me if I got pink polka-dotted shorts?”
Or ask her about something you genuinely want to know about her

Connect to the things that you’re actually curious about in life or what would fascinate you to learn about her.

Can she talk about things you love or invest your time in? What common interests do you share? Does she think like you or is she at least open-minded? What’s her opinion on something you’re passionate about? How does she like to enjoy herself? What are her values?

For example…

  • “About to faceplant in the snow while skiing this mountain. What’s your perfect weekend getaway?”
  • “Being a psych major, you’ve got me curious. Have you ever explored psychedelics?”
  • “So I’m really into self-development. I’ve been working on myself a lot lately — how do you feel you’ve grown over the last year?”
  • I’m sitting in bed reading X book and it’s making me question being a meat eater. Has any book ever changed you as a person?”
  • “Have you ever treated yourself to an epic, judgment-free home-cooked meal?”
  • “Do you believe people are good or bad, or some shade of grey?” or “Do you think most people can be truly monogamous or are we all still driven by our primal instincts?”
  • “I’ve been thinking lately about Black Mirror type stuff. Would you ever get a computer chip in your brain?”
  • “Is there ever a good reason to lie to someone you care about? Or is the truth always better?
  • “How do you try to disconnect? I’ve been taking some long walks without my phone and it feels surreal. Almost like how it was when I was growing up.”
  • “What’s your superpower? I can make any baby giggle in less than 3 seconds.”

There is no perfect follow-up message. Please remove that thought from your head.

You just need to give yourself permission to connect with her as if you two are already comfortably connected.

If you REALLY feel like you need context, you can always preface these messages with something like…

  • “I know this is random but….” or “Random question…”
  • “This may be out of the blue…”
  • “I’ve had this question on my mind all day…”
  • “I’ve been thinking a lot about X. You don’t have to answer if you don’t want to but…”
  • “I had to tell someone what just happened…”

All you’re doing here is signaling that you know this is unexpected, uncommon, or offbeat. That self-awareness can help someone feel like you’re a normal human who’s just trying to have some fun together.

But any one of the example messages are infinitely better than writing something safe, and forgettable. Even if you somehow came off a bit random or quirky or clumsy, at least it’s different. That’s so much more powerful.

Because different is the only way she can feel that you two have a special connection. And that’s what’ll get her excited to see you.

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I love hearing romantic success stories. Even after eleven years, I still get a huge smile on my face when a client shares their enthusiasm from a positive dating experience.

That’s why it’s so difficult when I sometimes have to challenge people on their so-called “successes”. It’s tough to tell them to temper their excitement because their victories may not really be victories.

A lot of people define their romantic success by the wrong metrics. I know this because I spent years measuring my love life wrong, too.

I used to think I was crushing it with women if I got a number, got a kiss, or got laid. It seemed pretty straightforward…

“If an attractive woman wants me, I must be doing something right.” Society and friends told me that dating success was only about sleeping with hot women.

But over time I realized that mindset was all backwards. Viewing dating in this way never brought me long-term fulfillment.

I was stuck chasing the next “win” and without it, I felt like a failure. I never became comfortable in my own skin. And I never found lasting relationships with the women I really wanted.

Because when you measure your dating success by external approval, you risk destroying your self-esteem.

Winning is the opposite of what you think

Wikipedia defines self-esteem as…

“An individual’s overall subjective emotional evaluation of their own worth. It is the decision made by an individual as an attitude towards the self.”

Self-esteem is how you view and love yourself for your internal qualities. It’s not how other people see you nor is it how you measure up to arbitrary societal standards.

I know attractive people who think they’re ugly and overweight people who absolutely love themselves. I know rich people who are miserable and poor people who are grateful for every day they’re on this Earth.

It’s not easy to suddenly adopt a healthy attitude towards ourselves. But you can start by honestly evaluating your behavior with women. Because your behavior constantly influences how you feel about yourself.

Your subconscious is always listening and over time, your actions will either raise or lower your self-esteem.

So think…

Do you often act in self-love, self-compassion, and self-acceptance? Do your actions align with your deeper values? Do you respect yourself and set your boundaries when you feel disrespected?

Do you prioritize your needs or do you hide them in fear of facing disapproval or judgment of others? Do you try to speak honestly and express who you are even it means other people may not agree?

THESE are the questions that should dictate your successes – in dating and in life.

Just because you hooked up with a hot girl doesn’t matter if you had to compromise your values to do it. Your self-worth suffers all for what…a fleeting orgasm?

Some wins are bad for you

I know what you’re thinking…how can dating an attractive person ever be a bad thing?

Again, it all depends on whether or not you’re sacrificing your self-esteem in the process.

Let me give you an example…

Maybe you finally got that gorgeous woman from your class to grab drinks with you. You had a seemingly great date. She laughed throughout the conversation, looked like she was having fun, and you even kissed her on the walk home.

That’s amazing, right?

But what if that same girl blew you off for weeks before now and cancelled multiple times last-minute? What if she only talked about herself the whole time and you went along with it to please her?

What if you avoided expressing your more quirky interests because you thought she would judge you? What if she was on her phone, casually ignoring you throughout the date but you never expressed that you wanted her to be present?

So yes, you got this girl to go out with you…but what did you sacrifice in return?

Did you feel heard and accepted for who you are? Do you think she respects you as an individual? Is she attracted to you or just the version you pretended to be? And it is worth pursuing someone who connected with you under false pretenses?

Most importantly, prioritizing her approval tells your inner critic that the real you wasn’t good enough. You reinforce that you need to pretend to be somebody else to be a desirable person. And that’s guaranteed to crush your self-esteem.

That doesn’t sound like success to me.

Bad wins will sabotage your future success

On top of lowering your self-esteem, measuring romantic success based on external “wins” sets you up for future failure.

You might believe that people will like you more if you figure out exactly what they want. But this only communicates to others that you’re desperate for their validation — and that’s a turnoff for almost everyone.

Being a chameleon is unsustainable. You’ll only find people who are attracted to that fake version of yourself. Simultaneously, you’ll push away people who would actually like you for you. And when you finally can’t keep up the charade, you’ll either lose your connections or end up being someone’s doormat.

The good thing is…there isn’t just one type of attractive person. Confidence is the sexiest quality imaginable – and it comes in all different forms and variations. And it’s something you can develop.

I have a client who recently started dating a girl who smokes. He told me that he knew he could never have a long-term relationship with a smoker.

He was afraid of being honest with her in case she didn’t want to see him again. He was thinking, “I can’t lose this connection” instead of “I need to stay true to myself.”

I told him to tell her the truth: that he was interested in casually dating, but that was it.

So what happened when he opened up to her on their second date? She went back to his place and they had sex.

He expressed what he wanted and even though it was different than what she wanted, she still found that self-confidence sexy as hell.

If you make your dating successes about self-love, you build real confidence and become more attractive to the people who genuinely appreciate you. That’s how strong, lasting relationships are formed.

If you make your successes about pleasing everybody, you may get a temporary high. But you’ll form connections with incompatible people, built on weak foundations, that will inevitably crumble.

Measure your internal effort, not just the external result

You need to evaluate your successes based on your effort to remain true to your values and respect yourself, not on the external result of women’s approval.

External approval: You introduced yourself to a woman with a rehearsed line you read from the internet.

Internal approval: You introduced yourself to a woman with something you genuinely felt or observed in the moment.

External approval: You let your cute co-worker rely on you and spend a lot of time together at work. You secretly liked her but only acted like her business buddy for months. You went above and beyond to help her on the job but never invited her to get more personal outside of work.

Internal approval: You invited your co-worker out, even if it meant you could find out she only saw you as a friend. You preferred to be upfront with your intentions rather than live in a fantasy world.

External approval: You finally got a girl to commit to a first date, but only after multiple last-minute cancellations and overall poor communication from her.

Internal approval: You walked away and focused on someone who was willing to invest in you. Or, you communicated your boundaries after she cancelled a second time: “My time is really valuable to me and I want to connect with someone who’s excited to connect with me.”

External approval: You had sex with a woman, but you had to pressure her or emotionally manipulate her into it.

Internal approval: You developed trust and comfort with a woman and had sex because of it. Or, she wasn’t quite ready yet, and you accepted her decision. Then, you waited until she was more comfortable or you chose to connect with someone else who reciprocated your desire.

External approval: You got a girl’s number, but you did so under the guise of being friends or helping her study.

Internal approval: You honestly invited a girl out to get to know her better on a personal level, even if that meant she might say no. The number was just a nice bonus.

External approval: You used your wealth and status to attract dates. You felt you needed to pay for expensive meals and experiences to get women to go out with you.

Internal approval: You used your personality to attract women because you want someone to like you for you. You bought some meals and split others. You invested money on dates only when you felt someone was authentically investing back in you.

External approval: You continued to date women who you knew wanted something more serious, even though you weren’t that interested in them. You wanted the attention even though you knew you were settling.

Internal approval: You broke it off with women you settled for to pursue women you genuinely desired. Or, you told those women you were only interested in a casual relationship with them.

External approval: You’re happy that a girl was so engaged and talkative on your first date. You purposely only talked about what she was interested in and avoided revealing your passions in case she didn’t find them appealing.

Internal approval: You shared your real perspective on things that matter to you and asked questions about subjects that engage you, too. You did this at the risk of her judging your hobbies, opinions, and interests.

Funny thing is, small internal wins end up leading to big external results.

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I knew an outgoing girl who had a lot of guy friends…or so she thought.

One day I told her, “You realize that most of these guys like you, right?”

She thought that was preposterous. She was almost offended by the idea and adamantly denied it. She said, “They’re just good friends.” When I dug a little deeper, I found out…

These “guy friends” were showing her interest left and right.

They always tried to hang out with her one-on-one. They texted and talked for hours on the phone. They bought her gifts. They bashed other guys she dated.

And they “jokingly” complimented her and got a little handsy with playful touches.

Eventually, these guys tried to make a move or confess their feelings. She had no choice but to reject them in an awkward way. Many of those connections deteriorated or fell apart altogether.

She was taken by surprise and that’s okay — she was young.

But what’s not okay is when I see this scenario play out among mature adults. The signs are obvious and it’s possible to avoid unnecessary pain.

I’ve called out guys for pretending to be a friend when they wanted more. Now I want to address the women who suspect or even know their guy friends are into them and avoid talking about it.

Women, it’s time to tell your guy friends that you see them as only friends.

If you really don’t know how he feels

Think of a guy friend who spends a decent amount of time with you. How are you supposed to figure out if he has feelings for you? Look at the signs.

Does he…

  • Invest massive time and energy in you? Does he message you almost every day? Is he always around you at work? Does he spend time with you instead of trying to meet any other girls? Does he hang out with you more than any other friend?
  • Note: If a straight, single guy spends more time with you than almost anyone else in his life, he’s probably interested! This is especially true if you’re not a long-time friend and he prioritizes you over his existing relationships.

  • Show you romantic interest? Has he touched you in more personal or intimate ways? Does he ever compliment how attractive you are? Does he often invite you to one-on-one activities at night? Has he ever said outright that he likes you?
  • Spend money or go above and beyond to support you? Does he offer to buy you dinner all the time? Does he surprise you with random gifts? Does he offer to take you on vacation together? Is he financially supporting you at all? Is he helping you at work more than anyone else, even at the expense of his time?
  • Get jealous of other men in your life? Does he disapprove of the guys you date? Does he tell you that you should be with someone better? When you start dating someone, does he get upset or stop reaching out for a while?

And for one final check, use your instincts:

Imagine you told him you wanted to go home with him, do you think he’d say yes?

If you’ve answered yes to any of these, your friend may be into you. Of course, this is all speculation. The only way to know for sure is to talk to him about it. And this is what so many women avoid.

If you know the truth but avoid the conversation

In my experience, the signs that a man is interested are quite obvious. I know that’s not always true but I want to be straight with you…

You probably didn’t need me to tell you the above signs. You already knew deep down that this guy wants more.

If that’s the case, you don’t need to keep guessing about his feelings. You need to admit and accept that you’ve been avoiding the conversation.

This isn’t to attack you or make you feel bad. I don’t think you’re a heartless person if you’ve kept things ambiguous. In fact, I believe most women who have been in the situation don’t have any malicious intent.

It’s fucking hard to reject someone. It’s an uncomfortable, emotional conversation. You might worry that you’re going to lose him altogether. Or you might worry that he’ll retaliate.

I also know that it can feel really good to have someone like him around. Society and social media tells women their value is based on how attractive they are to men.

And sometimes, you want emotional support from a guy who listens. Sometimes you want attention and to feel beautiful. Maybe you know this guy’s a good guy and want to have him as a potential backup romantic option.

Or maybe, it feels nice to be pampered by a guy who seems happy to do so.

So in return, you keep your feelings about him unclear. If he doesn’t bring it up, why should you?

The harm in being ambiguous

On the surface, being ambiguous seems like no big deal. But what you don’t realize is that many guys obsess over one girl they like.

They focus on her relentlessly and think of ways to win her over. They’re wracked with anxiety trying to figure out if she likes them back. They dream up an entire life together.

The longer this goes on, the more invested their heart is.

Maybe you think that if you never flirt back, reject his date ideas, and date other people — he’ll get the hint. He won’t.

I talk to so many men who hold onto any glimmer of hope for months or years. They only let go when they’ve heard you say the exact words that it’s not going to happen. Let me repeat — guys don’t take hints. You need to say something. And here’s why:

If the situation were reversed, wouldn’t you want to know the truth? Wouldn’t you want the chance to move on and find someone who likes you back?

The kindest, most considerate thing you can do as a good friend (and as a human being) is to be clear about how you feel. This is also the best route to salvaging the friendship and building trust.

When this topic isn’t addressed…someone’s going to get hurt.

What happens when you don’t face the elephant in the room

Avoiding the tough conversation almost always ends up the same way…

The guy can’t take hiding his feelings any more. Then he finally gets the courage to do something about it.

So he pushes things forward to the point where you have to give him an answer. Maybe he tells you he likes you or tries to make a move.

Now you’re stuck. You have to reject him at his most vulnerable moment. This often results in a tense or heated discussion where both parties feel hurt.

The guy realizes after all this time, his hopes were only a fantasy. He might even blame you for leading him on. He may distance himself and break off the friendship altogether.

This makes you think, “What a jerk! He only cared about trying to get with me, not having a friendship.”

But I would challenge you on that. A friendship can only work when both people truly want a friendship. If you know he’s into you and you let him get his hopes up, are you being a good friend?

When it gets to this point, everyone loses. You both feel used by each other for different reasons. You feel men only see you as a sexual conquest. Men think you used them for emotional or financial support while you secretly desired other guys.

I believe experiences like this are a major cause in the growing animosity between young men and women in dating.

This type of behavior leads to resentment, anger, distrust, and even hate. And when people get into an “us vs them” mentality, it encourages them to treat future partners poorly.

Romantic relationships suffer when everyone is adversarial and manipulative.

Avoid more pain and have the conversation

I’m asking you — communicate how you feel with the men in your life.

I know you might be afraid of the repercussions. That’s why the time is now.

It may be uncomfortable, but it will avoid more misunderstandings and pain later. Doing it early and sincerely gives you the best chance that a guy takes that rejection gracefully.

The longer you delay, the more crushed he will feel. This also increases the chance of fallout. Nip this in the bud and you can almost always resolve things peacefully.

The smoothest way to approach the conversation is when he’s first starting to show subtle signs of interest. Maybe he invites you to drinks alone or touches you lightly when hanging out. This gives you a natural context to share your feelings.

Otherwise, you can always bring it up gently when hanging out. Do it in a public space if that feels better.

Open up to him with something like, “I want you to know how much I care about you as a friend. We’ve never talked about it but I’m not sure how you feel about me. I’m just looking to be friends if that’s okay with you.”

He’s either going to accept the reality or move on.

If he walks away, then you know he never wanted to be your friend.

If he accepts you as a friend, this honesty will only strengthen your connection.

Clear communication is how we create more love for everyone.

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Our surroundings subtly impact our everyday life. Different environments have different effects on our state of mind.

When I write, I like background noise and activity. So sometimes I work at coffee shops because if I’m alone in my house, I can find it difficult to be creative in total silence.

When we get fired up about politics, online environments allow us to be more direct and even insulting than we would be in-person. People say things they’d never say to someone’s face.

When we go to a restaurant, the decor, lighting, and music dictates our mood. We’re more likely to feel intimate with someone in a dim room by candlelight than in a bright, fluorescent strip mall.

When we’re trying to make meaningful romantic connections with new people, the right environment is key.

Think about the most common places for finding new dates – online apps and bars/clubs. They probably feel safe and socially acceptable for meeting new people.

But…are they really the IDEAL environments to meet your future significant other?

To me, I think using these avenues is like setting a video game on the hardest difficulty. You can win with a lot of perseverance and luck. But with your limited time as an adult, is it the most efficient, effective, and enjoyable way to play?

So instead, prioritize environments that work to your advantage. Choosing the right surroundings will boost your romantic chances, help you meet compatible people, and encourage others to open up to you in a real way.

Environments based on commonalities

Finding common ground can make two strangers feel like they’re part of a tribe. It’s why we seek out communities based on similar values or interests.

If we talk to someone at salsa class or on a ski trip, we assume they must be somewhat like us. They spend time thinking and participating in something we feel passionate about – so they can’t be that bad.

We’re more likely to give people with similar interests a chance. The barrier to starting conversation is much lower.

When you have nothing in common with someone, you’re just another one of seven billion strangers to them. They’re less likely to feel immediately drawn to you and will be more hesitant about getting to know you.

I had a client who was frustrated with online dating. He felt many women had little content on their profiles to connect with. So one day he told me about a woman he wanted to message via LinkedIn.

Initially, I was hesitant. LinkedIn is for business and I didn’t want men to start treating it like a romantic playground. But then he told me more about the specific woman he wanted to message.

They were both in a niche science field. They were deeply passionate about it even outside their day job. They wrote papers, attended conferences, and shared content online about their specialty.

I helped him message her and within a week, they met up and started dating. I couldn’t believe it. Since then, I’ve known many couples who met through social media and it’s often because they had something they could immediately connect on.

Examples: alumni events, conferences, music or art festivals, conventions, museum social nights, volunteering or fundraisers for a cause, any niche activities/hobbies/classes like rock climbing, standup comedy, or photography

Environments with your friends or extended social circle

We value the insight and opinions of our friends. I bet there’s a book or show you’re obsessed with that a friend originally recommended.

We also trust our friends’ judgements about other people. If a friend thinks someone is cool, we’ll give that person a chance, too.

So look for environments where you have a common social connection.

Once a person finds out you’ve got a mutual friend, they will be more open to meeting you. They’ll be warmer and more patient in trying to connect with you.

No one wants to be a jerk to someone in their social circle.

At a public venue like a bar, people don’t have that same consideration. They can be more standoffish and in rarer cases, outright rude, without concern for the consequences.

The strongest form of using social connections is a personal introduction. If you see a friend talking to someone you want to know, ask them to introduce you. A positive, personal referral is worth 5 cold introductions to strangers.

Examples: weddings, birthday/house parties, a friend’s music or art show, a friend’s work party/event, co-working spaces

Environments where you already have value

Social proof is a psychological and social phenomenon wherein people copy the actions of others in an attempt to undertake behavior in a given situation. (Wikipedia)

So just like we trust our friends’ opinions, if groups of people see a stranger as valuable, we’re more likely to admire them, too.

Think about a random singer at a small venue. Nobody knows him. Yet you’ll notice tons of women trying to get his attention and talk to him. If he gets off stage after his set and walks over to the bar, he’ll often get mobbed by people.

He sang songs and gave people a good time. He immediately has status in that room. You can accomplish the same thing in a variety of ways:

  • Become friends with the staff at a place. Greet them and make small talk with them regularly so they get to know you. Then when they’re excited to see you, other people take notice and become curious about who you are.
  • Showcase your existing skills. If you’re good at something, share it with others. Present your art at a small gallery, play a local gig with friends, speak at a conference, or join an outdoor/sports group of something you’re already experienced in.
  • Invite people to an activity and tell them to bring friends. This could be something like bar trivia or axe throwing. If you’re the guy who brought everyone together for a good time, you’re the awesome social connector that people want to know.
  • Host something. Throw a party and get people to invite others. Set up a wine tasting or silent disco. Start a fundraiser. Open a club at your university. The host of any event is the person of the hour. You’re responsible for people having this great experience.
Environments where you’re rare or unique

When we have too many options in life, we can struggle to choose between them. This is called “choice overload”.

Platforms like online dating enable us to rapidly connect with more people than ever before. But, it comes at a cost.

You talk to dozens of people at once. You constantly compare your options. You commit to meeting up with only one foot in, just in case someone else better comes along. And when it’s time to meet, you back out because you know there will be another opportunity around the corner.

But in environments where options are limited, you weigh each option more carefully.

Find avenues where you’re a scarce resource that people want. If you’re one of the few single people or one of two guys in a class of women — you’re a hot commodity. 

I first noticed this at small gatherings like dinner and house parties. Even though there might only be 5-15 people, the conversion rate of the single people who were interested in each other was ridiculously high.

Compare this to a bar in a major city. There might be hundreds of people and some guys will talk to half a dozen groups of girls or more. And yet, only a handful of people will end up getting together. The rate of connection is substantially lower.

This principle works for making friends as well.

I’ve taken classes and group tours around the world. If you and someone else are the only people under 35 there, you always gravitate towards each other. The options to connect with someone of the same age are so limited, you look past differences and make an effort when you maybe wouldn’t otherwise.

Examples: smaller dinner/house parties, classes/hobbies where you’re the rarer sex (salsa, for example, has a high ratio of women to men)

Environments where you’ll see the same people again

Why do some people act cruel to others online when they’re amicable in their daily life? Why do some people go to Vegas, get really shitfaced, and do wild things, when they never would otherwise?

It’s because they know they’ll never have to see those people again. There’s very little social consequences.

So goes the idea, “What happens in Vegas, stays in Vegas.”

This phenomenon works the other way around, too.

If you’re going to be around the same people for hours or expect to see them again soon, you know you can’t treat them poorly. You can’t be a dick to someone in your three-hour-long cooking class or else things will get real awkward and tense, real fast.

So instead, you try to be cordial and casually engage them. You allow yourself to get a little familiar with them and as we know, familiarity breeds fondness.

I’ve seen this play out in many work environments like restaurants or corporate offices. People see the same co-workers day after day. Even if there’s only a small group, people start getting together.

Anyone who’s worked at a place like TGIFridays will tell you it’s just a who’s who of hookup stories.

I also see this at my retreats. Eight total strangers get together from various walks of life. In normal circumstances, many of these people might never become friends with each other. But because they’re spending four days in the same house working towards a common goal, they find ways to connect and often end up forming tight-knit bonds.

Examples: retreats, work environments, hostels, classes like CrossFit/improv, social/sports clubs, backpacking or traveling groups, school campuses, becoming a regular at a coffee shop or a bar

Don’t make meeting someone unnecessarily hard for yourself. Put yourself in the right places and half the work will be done for you.

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The average American man has only one close friend. In England, 2.5 million men don’t even have that.

Loneliness is the #1 reason people seek counseling. And if we don’t get that help, isolation can increase the risk of premature death up to 32%.

So in the sea of New Year’s resolutions chasing love, sex, money, and the perfect body – I want to propose something different:

Commit to making two real friends this year.

Why two? Because different friends provides unique experiences, perspectives, and relationships. And it’s too easy to use one person as your end-all-be-all source of support.

Also, sometimes one person is out of town and you still want to watch the game with a bro.

As adults, I think of lot of men lose sight of the importance of good friends. And being proactively social isn’t something that always comes naturally to us.

I used to think having a big group of friends was something from my distant childhood. As people moved away for school or work, my social circle dissolved. I figured that was a normal part of becoming an adult.

So in my early to mid-20s, I became a lone wolf (like so many other men).

I built up my career. I networked and partnered with people in business. I focused on meeting women. And when I dated those women, I spent a lot of my time with just them.

Friends were nice to have, but not an absolute priority. I think that’s how a lot of men feel about adult friendships. That is, until you realize how much you actually need those male bonds.

Friends are crucial to our long-term growth and happiness.

When my dad got sick, my buddies took me out to distract me with fun times. When I was feeling socially anxious, my friend pushed me to talk to people with him – which eventually led to meeting my wife.

When I was a naive, straight-laced young man, friends challenged my way of thinking. This lead me to reading hundreds of books that permanently changed my beliefs and notions of what’s possible.

When I was terrified of leaving a job I hated, my friends gave me the courage to quit and pursue my dreams as a coach. And various friends have worked with me to host retreats around the world and launch my first online group coaching program.

Good friends can provide an invaluable support system and motivation. They make you feel loved and connected. They share joy with you. They can push you to become a better version of yourself.

Now looking back, many of the best moments in my past five years were shared with friends.

I got to be best man for the friend who helped me meet my wife. I experienced Mardi Gras in all its glory with a great group of guys. I lived on a remote island with world-class entrepreneurs where we built our own facilities.

I’ve shared incredible meals and taken breathtaking hikes through a dozen countries with adventurous friends. My wife and I just hosted a holiday party where we brought friends together to play music and fight over Super Smash.

Those are some of the happiest moments of my life.

And because of those experiences, I’ve realized how meaningful is it to be there for someone else, too. I find immense fulfillment in supporting the people I care about.

I get it that feels tough to make close friends.

When you’re young, it’s easy to call someone up and hang out. You’re also in environments where social circles are pre-made for you.

When you’re an adult, you’ve got endless responsibilities and a busy schedule. With everyone getting married, having kids, and working full-time jobs, it seems impossible. And if you don’t already have some acquaintances, then you’ve got to talk to random people in new environments.

But it doesn’t have be as complicated or challenging as you think. You just have to invest a little proactive energy to help things along.

Many guys are in the same position as you. They want more friends but feel clueless or nervous about putting themselves out there. So they don’t take the initiative.

But the second you show someone that you’re thinking about them, want to connect, or want to positively influence their life — they will reciprocate. You’ll encourage them to open up, think about you more often, and want to invest back in you.

Think about someone you already know and want to further connect with. Take that first step to reach out. Be curious about what they’re excited about and are looking forward to. Send them an article, book, or album recommendation you know they’d love.

Invite them to join you on a new biking trail or to play soccer with a couple of friends. Host a board or card game night. Introduce them to your new hairdresser to get a stylish cut. Set up happy hour drinks with a couple of co-workers.

Pick one person, hit them up, and show them you’re trying to be a good friend.

If you don’t have someone like that, then take the smallest step possible to meet new friends. That just means showing up.

Show up to a social environment for something you’ve wanted to try. Go to axe throwing, a small music show, or join a class for something you’ve wanted to learn. Then just focus on being present and enjoying the activity for yourself. Remove the expectation of trying to talk to anyone the first few times.

Being in the right place at the right time will lead to natural opportunities. People will talk to you on their own. And as you get more comfortable in those environments, casually introducing yourself to new people becomes infinitely easier.

Creating or maintaining any worthwhile relationship requires some effort. But the return of investment of good friendships is immeasurable.

We all need someone who can be honest with us when we can’t be honest with ourselves.

We all need someone we can trust and rely on, even during our toughest times.

We all need someone we know cares about us when we feel alone in this world.

We all need someone we can be that person for, too.

I believe all this will cultivate more meaning and happiness not only in this New Year, but for many years to come.

Ready to effortlessly meet new friends and women, too? Check out my new live group coaching program. Registration closes January 15th.

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Today’s article is from my close friend, Jason Connell. As a consultant, he’s worked with multi-platinum recording artists, professional athletes, top government officials, and Fortune 500 executives. I also selected Jason to help run my confidence retreat in Austin, TX. Today Jason is in training to become a clinical therapist and meditation teacher.

In January, Jason and I will be hosting a live online coaching program called Effortless Encounters to help men meet amazing women in their everyday lives. You can sign up here before registration closes on January 15th.

Without further adieu, please welcome Jason….

There used to be a guy in my social circle, A*, who spent years chasing women. His goal: sleep with 40 women. One night I asked him, “Dude, why is sleeping with 40 women so damn important to you? What difference do you think it’ll make?”

He told me, “Well once I do that, I’ll know I’m attractive and desirable. Then I can be happy and confident.”

A few years later A* texted me to tell me he finally did it! I asked, “So did this change you? Are you happy now? Can nothing shake your confidence?”

He replied, “No…I think I need to sleep with 10 more women.”

A lot of guys believe that once they have a girlfriend or sleep with a certain number of women, their self-esteem will magically improve. Consequently, guys spend huge chunks of their lives searching for lines, techniques, and quick hacks that will make them more attractive.

But that’s the wrong path.

This is the male equivalent of wearing heavy makeup, a pushup bra, and high heels. It might make you more appealing but only in a temporary, superficial way. Beneath your lines, fake confidence, and strategies, you’ll still be controlled by the same insecurities.

Until you improve your mental health and heal emotional wounds, you’ll struggle to get the love and sex you deserve.

Investing in your mental health is the most effective way to become more attractive. From there, everything else will start falling into place.

Foster joy within your life

One of the most fun – and attractive – ways to improve your mental health is to increase the amount of joy you experience. Learning to fall in love with life has a magnetic power to it. Without meaning to, you’ll draw great people and opportunities to you.

Here are three of my favorite approaches…

1) Take yourself on a date. You know how you’ve spent a lot of time, energy, and money trying to delight other people? Now it’s time to invest in yourself.

The goal is simple: spend a few hours on your own, with your phone off, doing real-world stuff that makes you happy. For example:

  • Relax with a massage or a session in a flotation tank
  • Wander through a cool neighborhood and check out different shops
  • Go to the movies and order a huge box of popcorn
  • Spend the night reading a great book – I’m loving “The Way of Kings” by Brandon Sanderson
  • Eat all of your favorite foods
  • Go for a drive while listening to your favorite album
  • Play games at the nearest arcade or barcade (I’m a sucker for pinball and guitar hero)
  • Sit in a hip cafe and journal for a while
  • Treat yourself to a nice cigar and scotch

I know the idea of taking yourself on a date sounds strange, but try it.

Many of us have been depriving ourselves of the same compassion we give to others. When we celebrate and enjoy our own company, our lives and self-esteem become notably better (which coincidentally makes you more attractive).

2) See your friends more often and tell them a few secrets. Countless men are dying to have great guy friends but are afraid of taking initiative. Don’t be that guy. Instead, emerge as a leader in your circle by spending time with people you love and organizing engaging activities.

Shoot a quick text to one (or a few) of your friends inviting them to do something like grab a beer after work. In fact, stop reading this right now to text a few people.

If you’re feeling ambitious, organize a larger group. One fun idea: invite 5 or 10 people over, and have everyone bring their favorite six pack. Then you can do a beer tasting together. You can also invite people to a sports event, pool hall, camping or hiking trip, or have people over to play games.

If you have a group of friends you love but you don’t live close to each other, schedule a conference call. Once a month my guy friends from college and I get on the phone to shoot the shit for an hour. Sometimes we just catch up and bust each other’s balls. Other times, we help each other deal with difficulties like heartbreaks, miscarriages, and career hurdles.

Two important things to keep in mind:

First, realize that you’ll probably have to take a leadership role in your social life. This is a good thing. Not only will it position you as the most influential person in your circle, it will improve your love life. As Nick has pointed out many times, being a skilled leader is one of the most attractive qualities in a man.

Second, open up to your friends. Tell them about what you’re proud of and what you’re wrestling with. Ask questions about them, too. Many men struggle with vulnerability and connection. Opening up and being curious about the people in your life will create stronger relationships.

Not only will these steps bring you joy and security, they will also make dating easier because you’re more skilled at forming connections than most guys. I cannot overstate how attractive a vibrant social life is to women.

More on making friends here.

3) Always work to improve yourself. As a man, part of your nature is to continuously conquer things. While our focus tends towards money, strength, status, influence, and women, there’s an even greater achievement: becoming the best version of yourself.

On a simple level, this means finding great hobbies, diving into your interests, and sharpening your existing skills.

On a deeper level, this means improving how you engage with the world. You can do this by healing old wounds, learning new skills, traveling, staying open to compliments and criticisms, developing your spiritual side, sitting with discomfort, taking calculated risks, finding work you love, and giving back to your community.

Eliminate the darkness that has been quietly plaguing you

Countless men wrestle with hopelessness, isolation, desperation, and depression.

Most of us try to ignore those feelings or deny their existence. Bad idea. Doing that only gives them more power.

Instead, we need to learn to defeat our demons. Here are three techniques:

1) Develop a gratitude practice. Our minds have a habit of obsessing over what’s wrong and failing to notice what’s right. This is called the “negativity bias” and it sabotages our self-esteem by making us think we are far worse – and less attractive – than we really are.

Thankfully, we can counterbalance the negativity bias by practicing gratitude.

I suggest something simple to start. Each morning write down three things that you’re grateful for and a quick reason why. This could be both about yourself and your life.

Doing this will help shift your focus and encourage you to notice how amazing you – and your life – actually are. One of my friends said this habit felt like it was rewiring his mind. Research backs this as well.

If you’d like a slightly more involved practice, I’m a fan of the Five Minute Journal.

2) Improve your physical health. In some cases, we can defeat the demons simply by being more healthy and active. If you’re not already exercising and eating well, start small but start now.

A simple approach that will get you 80% of the way there on the diet front: quit drinking soda and other sugary drinks. Then have a smoothie for breakfast, a salad for lunch, and something healthy-ish for dinner. If you can build those couple of habits, you’ll end up healthier than most people.

As for exercise, find something you love and then begin doing it even once a week. This can be as simple as a jogging program (I really like Couch to 5K) or as involved as spin, crossfit, or yoga. More on getting in shape while having fun here.

3) Stare your demons straight in the eye. Most of us try to ignore our demons because they’re unpleasant and difficult to deal with. But ignoring parts of ourselves is never a good idea. A much better approach is to acknowledge and investigate the darkness.

In my 20’s, I was extremely insecure about money. When I finally found the courage to admit that I had an unhealthy attitude I asked myself, “Why are you so worried about money, man?”

“Well I’m afraid of running out and going into debt.” Each time I got an answer, I dug deeper by asking myself, “Why do you feel that way?”

Eventually, I got to my core fear. I realized I was afraid that I ran out of money, no one would take care of me, and I’d have to face the unbearable reality that I wasn’t worthy of love or connection.

I know that sounds extreme but many of our surface-level stressors have deep roots. By becoming curious about the thoughts and feelings that distress us, we can better understand and master them.

Note: If you’re looking for an even more effective approach to dealing with complex feelings and emotional mastery, see the PS at the bottom of this article.

Learn to defeat anxiety

Your success in life is largely governed by your ability to handle anxiety.

If you’re afraid to go up to that stunning woman and say hi, then you’ll probably never meet her. On the flipside, if you learn to approach her, strike up a fun conversation, and ask her out, you’ve unlocked a world of potential.

Here are three approaches to overcoming anxiety and making it easier to leave your comfort zone:

1) Meditation. When people envision meditation, they often think of weird hippies and spiritual poseurs. Really, meditation is a form of mental training that positively impacts your happiness, confidence, awareness, and anxiety.

Here’s a simple practice to get started:

  • Sit in a chair with your feet flat and your spine straight. You should feel somewhere between relaxed and alert.
  • Set a timer on your phone for two minutes and close your eyes.
  • With your eyes closed, breath in and out through your nose.
  • Attempt to focus on your breath. When you breathe in say, “in” in your head. When you breathe out, say, “out” in your head. When you notice your mind drifting, simply bring your attention back to your breath.
  • At the end of the two minutes stand up and go about your day. As you get more comfortable with meditation, you can add more time.

The goal is not to clear your head of thoughts. That’s not possible. Instead, it’s about resting your attention on a single point of focus. When you notice that your mind has drifted from whatever you’re focused on, gently bring it back.

If you’d like additional instruction on meditation and how it can improve your life, check out the app, “Waking Up“.

2) Progressive desensitization. Nick makes brilliant use of progressive desensitization in his coaching for men.

Progressive desensitization is a simple technique: slowly but steadily expose yourself to the stuff that makes you anxious. Over time, you’ll become more and more comfortable with the things that used to cause discomfort.

The trick is to start small.

If you’re nervous about striking up a conversation with a stranger, don’t worry about it. Instead start with something easier, like making brief eye contact with a waiter or bartender. Once that becomes comfortable, try saying hi.

As that becomes easier ask, “How’s your day going?” From there, consider sharing a bit about how your day has been. Keep moving the needle until you can strike up conversations with random people.

Give yourself a few days, or even a week to get comfortable with each step. If one step is too big, break it down into more manageable pieces.

When you succeed, treat yourself (I like pizza) to celebrate and reinforce good habits.

Approaching your anxiety this way will nudge you out of your comfort zone and put you on the fast track to mastering your nerves.

Note: if this approach to building confidence and mastering anxiety resonates with you, check out Nick’s and my program “Effortless Encounters”. We blend evidence based practices like progressive desentization with real-world experience to help you form amazing relationships with the women you want.

3) The deathbed exercise. I use this exercise when I’m struggling to take action on something important to me.

Close your eyes and envision you’re on your deathbed. Now imagine looking back on two versions of your life.

In the first version, fear was your master. You wanted to travel, ask your crushes out, and write a book, but you were too afraid to do any of those things.

Now, imagine a second version where you mastered your fear. This is a vivid life where you travel, go on dates with women you desire, and write books.

Compare and contrast the two possible lives.

The life defined by fear ends up muted, subdued, and under-lived. The life that masters fear is vibrant, wildly alive, and exciting.

Then remind yourself of one more thing: though we know we will die, we don’t know when or what happens next. All we know is that we’re alive now and the decisions we make in this moment have the potential to color everything.

If you’re anything like me, going through this exercise will flood you with the awareness, energy, and motivation to overcome the obstacles holding you back.

Putting it all together to improve your mental health

We’ve covered a lot in this article and I want to leave you with a few ideas:

  • When you think about improving your mental health, think in terms of moving a needle, not flipping a switch. Slow methodical change fosters far better results than trying to do everything all at once.
  • Focus on one thing at a time. Doing so will make a dramatic – and sustainable – difference in your life. Once that thing becomes natural, you can move on to a new change you want to make.
  • You can do all of this in environments where you’re likely to collide with women you’d be interested in. So if you’re getting friends together for happy hour, and you like women who are a bit edgier, choose a grungy dive bar. Likewise, if you’re taking yourself out on a date, and you like nerdy women, browse a used bookstore or go for a walk on a college campus. And as you work on getting your fitness together, keep in mind that dance classes and yoga studios are filled with beautiful, fun women.

I know it’s tempting to click away from this article and try to find another tip to magically boost your confidence, or search for some line that will make your crush fall head over heels for you. But both you and I know that doesn’t work.

Instead, make a meaningful investment in your inner well-being. Everything in life flows from your relationship to yourself. The more connected you are with yourself, the more attractive you will become to amazing women.

PS What if you’re really struggling with your mental health?

I spent two years in therapy. It was the best thing I ever did for myself (and my love life).

Try improving your life on your own. Read, experiment, reflect, work with Nick, etc. But if you’ve been doing this for more than a few months and you’re not making meaningful progress, I urge you to seek the help of a licensed mental health professional.

Mental health problems are almost never your fault, but they are your responsibility.

Take control of your life now and get the help you deserve. No matter how old you are, your life will be better for it.

Besides, why bother dealing with more suffering than necessary? You deserve the best life you can create and if that requires getting help, so be it. You can find detailed instructions on finding a great provider here, and you can read about my experience in therapy here.


Hey, Nick here. If you enjoyed this article, consider doing two things:

First, check out “Effortless Encounters”, our live online training program to help men meet great women in their everyday life.

Second, subscribe to Jason’s blog. Jason writes about confidence, social interaction, self-awareness, personal development and more at JasonConnell.co. He’s hand selected a few of his articles that my readers will love.

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