Dear Sugars

The Sugars, along with the fiction writer George Saunders, field letters from people who are chasing their creative dreams but frightened by the practical and financial risks that come with that pursuit.

In a heated moment, a mother reveals a dark chapter from her childhood to her daughter, then immediately regrets it. What now? In this week’s episode, the Sugars tackle this and several other questions, including how to handle a brother-in-law who treats your vacation as his own free childcare; what to do when your best friend’s husband asks you to lie; and why we sometimes recoil at very public displays of grief.

"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."

There’s incredible power in saying “yes.” It opens up avenues and allows us to be brave. In Cheryl's case, it’s what led to her becoming Sugar. But saying yes to life's opportunities can also have its risks. This week, the Sugars are joined by Oprah Winfrey to discuss when to say no, how to say no, and what happens in the wake of that.

The Sugars are back for another batch of rapid-fire questions and answers. In this round, the Sugars take on six questions, ranging from a letter writer who is jealous of her sister's wealth, to a young woman who is growing impatient for a proposal from her longtime boyfriend, to a person wondering if people ever really change.

In this episode, the Sugars grapple with a difficult question — how do we make sense of the fact that very bad things can happen to people who have done nothing wrong? They discuss a letter from a visual artist who has just learned he is losing his sight, and another from a woman whose life has been transformed by her daughter's life-threatening condition.

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.