Encore: Should I Intervene?

This episode was originally released on May 26, 2018. In this "rapid fire" episode, the Sugars read letters from four women who each have one not-so-tiny reservation about the men they’re dating. A Black woman is dating a white man who is unwilling to talk about race issues, claiming that she’s “too sensitive.” Another woman’s boyfriend, a Christian, is having second thoughts about dating her because she’s an atheist. The Sugars tackle these issues and more, and weigh in on which can be ironed out and which should be deal breakers.

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, she sent an update. So, are they still together? Have any of his past traumas manifested in their relationship? The Sugars find out.

This episode was originally released on August 19, 2017. It’s never easy to talk to our romantic partners about their bodies, especially when it’s about weight. The Sugars, along with writer Ashley C. Ford, answer letters from people questioning their relationships because of major changes in their partners’ bodies.

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 All Repair. Episode 2 is already waiting for you. Listen on Apple Podcasts, Spotify or wherever you get your podcasts.

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.

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.

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.

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.

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.

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.