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.

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.

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.

At age 18, we are granted the rights and responsibilities of adulthood in the eyes of the law. But for parents of young adults, it’s not so clear cut. When is the right time to wean your children off the family payroll? The Sugars tackle this question with the help of Dr. Kate Gale. This episode was originally released on December 23rd, 2017.

Produced by WBUR, Boston’s NPR, in partnership with The Trace, The Gun Machine looks into the past to bring you a story that most Americans never learned in history class: how early partnerships between mad scientist gunsmiths and a fledgling U.S. government created the gun industry in the Northeast, and how that industry has been partners with the government ever since. Host Alain Stephens examines how this 250-year relationship underpins all Americans’ interactions with guns — including our failures in dealing with the fallout of gun violence. The Gun Machine episodes drop every Wednesday, starting Oct. 4, 2023. Listen and follow on Apple, Spotify, Amazon Music and wherever you get your podcasts. https://link.chtbl.com/thegunmachine

Snooping on your spouse is generally ill-advised, but what if he or she has an addiction and is constantly lying about it? The Sugars and writer Ariel Levy answer this question in this episode, originally released on December 2, 2017.

This is part two of the series on early childhood death. The Sugars read letters from parents who worry that their grief may overshadow their surviving children. They are joined by the writer Emily Rapp Black, who decided to have another child after learning that her son had a fatal congenital disorder.

Her grandmother always introduced her as the “chubby one.” Now, she vacillates between moderation and binge-eating. “It’s only when my pants are nearly impossible to button that I force myself to lose weight,” writes the letter-writer who calls herself Body Negative. “And then the pattern starts all over again.” The Sugars discuss and share their own struggles with body image.

"What do I want?" This is the question Oprah Winfrey finally asked herself, after years of struggling to say "no" to people in her life. In the second of this two-part series, the Sugars continue their conversation with Oprah Winfrey on when, why and how to say "no."

In this episode, the Sugars answer letters from letter writers who want to have sex less frequently than their partners do.

In the Empty Chair series, the Sugars discuss early childhood death, an absence that can be ever-present. In Part 1, they read letters from siblings who live in the the shadow of their parents’ grief. This episode was originally released on November 4th, 2017.

When the Sugars answered a letter from a woman who felt trapped in the role of "wicked stepmother," dozens of listeners wrote in asking the same question: what about the stepchildren, who have no control over the restructuring of their family? This episode, the Sugars respond with an episode devoted to the other side of the story.