In this episode, the Sugars take a question from a young woman whose boyfriend recently broke up with her because of uncertainty about his sexuality. The letter writer is heartbroken, confused, and wondering if she should wait for him while he figures it out. The Sugars are joined by Dan Savage, author of the sex advice column "Savage Love" and host of the "Savage Lovecast."

Money makes us crazy. In this episode, the Sugars take questions from two letter writers struggling with their relationships to money. The first, an aspiring playwright, feels guilty about all the advantages that her parents' wealth has provided to her. The second, a divorced mother, is unable to control her spending and is on the verge of bankruptcy. They're joined by the writer Sean Wilsey, who wrote about his own complicated relationship to family wealth in the acclaimed memoir, "Oh the Glory of it All."

In this short episode, the Sugars take a question from a 23 year-old woman who is engaged to the man she's been dating since she was 19. As a child of divorced parents who married young, the letter writer knows there are risks. As she prepares to tie the knot, she wonders whether she should be more concerned about those risks.

Every child has wondered of their parent: What were you like when you were my age? Who were you before I was here? And every parent has to decide how honestly to answer those questions. The Sugars discuss with poet and author Mary Karr, who has written three memoirs about her reckless youth and raised a son who was intimately familiar with those years.