This episode was originally published on August 12th, 2016. The Sugars hear the latest from "Head or the Heart" -- a woman who'd fallen head over heels for a man with a troubled childhood. Everything seemed perfect, and yet, she couldn't help but wonder if the traumas of her love's past would surface at some point in their relationship. "Head or the Heart" became the first letter-writer ever to join the Sugars on the show. The Sugars asked her to write to them in six months to let them know how -- and if -- things were going with her boyfriend. Nine months letter ..read more

Introducing Beyond All Repair, a new WBUR podcast from producer emeritus of Dear Sugars, Amory Sivertson. This series tells the story of a murder, but also the woman who was accused of that murder, Sophia. Sophia was newly married and 6 months pregnant when she was charged with murdering her mother-in-law in 2002. She gave birth to a son in jail that she hasn’t seen since, and for the last three years, she’s been telling me her story in hopes of getting justice for her mother-in-law, of having a chance of meeting her son, and of finally being believed. This is the first chapter of Beyond ..read more

Our loved ones are the people who are supposed to understand us. But what if they just...can't? Where do we turn then, and how do we fight the feelings of resentment that this lack of understanding can stir up? This episode was originally released November 11th, 2016 ..read more

The Sugars' conversation on friendship continues with a handful of letters concerning male-female friendships. Is there such a thing as a platonic relationship between a heterosexual man and woman? Can male-female friendships be as emotionally satisfying as same-gender relationships? What do you do when a friend crosses a romantic line? The Sugars discuss it all in rapid-fire fashion ..read more

Everyone has had a friendship quandary of some sort in the past, right? This week, the Sugars take on frequently asked questions in "rapid fire" fashion – from hating your best friend's significant other, to hating her politics ..read more

Whether you’re 5, 15, or 50 years old, it can be difficult to usher a stepparent in and out of the family unit. In today’s episode, the Sugars answer letters from stepchildren who have fraught relationships with their stepparents. What is a stepparent’s responsibility to a stepchild after divorce? And what can be done if you don’t like the person your parent chooses to marry? This episode was originally released on April 28th, 2018 ..read more

Buzz Bissinger owns more than 100 pairs of leather pants and over 200 pairs of leather gloves, having spent more than $600,000 on leather goods in the span of three years. Mr. Bissinger has a spending addiction, and he joins the Sugars to offer guidance to a letter-writer whose therapist and family don’t take her spending seriously. This episode was originally published on April 14th, 2018 ..read more

How many times have you heard this: "I love him, we're great together, but..."? There's always room for doubt, even in the happiest of relationships. So this week, the Sugars take on some of those doubts in rapid-fire fashion. This episode was originally published on January 5th, 2017 ..read more

Most of us have days when we don’t feel attractive. But in this episode, the Sugars read letters from people whose faces are at odds with conventional ideas of beauty. Writer Ariel Henley joins to talk about her own facial differences. Henley was born with Crouzon Syndrome, and underwent dozens of surgeries that changed the shape of her face ..read more

Privilege comes in many forms: socio-economic privilege, gender privilege, heterosexual privilege, to name a few. In this episode, the Sugars reply to two letter writers who are facing different forms of privilege. They discuss with Catrice M. Jackson, a leading voice for racial justice. This episode was originally published on August 11th, 2018 ..read more