Dear Sugar Radio

Listen To Your Heart — Radically Empathic Advice
From Cheryl Strayed And Steve Almond


The universe has good news for the lost, lonely and heartsick. Dear Sugar is here, and speaking straight into your ears. Hosted by the original Sugars, Cheryl Strayed and Steve Almond, the podcast fields all your questions — no matter how deep or dark — and offers radical empathy in return.

New episodes are released weekly.

Have a burning question for Sugar? Email dearsugarradio@gmail.com or submit it here, and it might get answered in a future episode of the show. 

Dear Sugar: I’m Falling For My Ex-Husband

The Sugars take a letter from a 62-year-old divorced woman who is shocked to find herself considering a reconciliation with her ex-husband, after years of unhappiness inside the marriage. The situation is further complicated by the fact that he is engaged to another woman.

When Politics Is Personal: Romantic Partners

The Sugars wonder if romantic relationships can survive profound political differences. They take a question from a young woman who prides herself on being a strong feminist, and worries her boyfriend doesn’t share her views. They also hear from a progressive Democrat who has married into a conservative Oklahoma family and is finding it increasingly difficult to stay silent about her true beliefs.

When Politics Is Personal: Friends & Family

It’s election season, and while politics may not seem like the domain of Dear Sugar Radio, it can become deeply personal. In Part 1, the Sugars look at how politics can get in between our relationships with friends and family—whether it be our parents voting for a candidate we despise, or our friends sharing views we find abhorrent on social media.

The Inevitable Guilt Of Motherhood

Being a mother means feeling conflicted in some way about the balance between raising one’s children and the rest of life. The Sugars take two letters from women in the midst of such conflicts—one from a career-driven young woman who cannot fathom going back to work after the birth of her son, the other from a daughter who feels caught between the needs of her dying mother and her newborn baby girl.

Dear Sugar: How Do I Stop Lying?

We revisit an episode about compulsive lying with guest Leslie Jamison. The Sugars take on a letter from a young woman telling her friends about imagined experiences of rape and loss.

The Infidelity Episodes: The Other Woman

The Sugars return with another installment in the Infidelity Episodes — looking at the often-overlooked experience of the other woman. After the Sugars had taken on the Betrayed and the Betrayers, they received dozens of letters from women struggling to make sense of what it means to be involved in a cheating situation, while being neither the one who cheats nor the one who is cheated upon.

The Irrational Jealousy Of Lovers And Friends

The Sugars take on jealousy — the fiery, irrational kind we feel toward our lovers and friends. They read a letter from a woman struggling with her competitive instincts toward an attractive new friend of hers, and from a man having trouble with his wife’s close friendship with an old lover.

Letter From A Closeted Atheist

The Sugars take a letter from a young woman who was raised in a deeply Christian household. As she has grown older, her beliefs and values have become increasingly at odds with those of her parents. She loves and respects her mom and dad, and doesn’t know how to tell them that she is no longer a Christian — which to them will mean her eternal damnation.

Friends With Benefits, Foursomes And Other Messy Relationships

What if the man you love wants to break up but keep hooking up? What if he wants to see other people? How should you handle your jealousy toward a long-distance lover’s friend of the opposite sex? What happens when a foursome between couples reveals hidden feelings? If someone isn’t over an ex, should you stay close or walk away?

The Tale Of The Wicked Stepmother

There’s a long tradition in fairy tales of the wicked stepmother. And the archetype endures in contemporary life. The Sugars take on two real-life versions of the tale — a mother whose ex-husband’s new wife wants the children to call her “mom,” and a stepmom who feels trapped in the role of the storybook villain.

The Secret Lives Of Lovers

The Sugars take a question from a newly married woman who is facing a nightmare — the man of her dreams has turned out to be someone else entirely. They are joined by the writer Julie Metz, who tells the story of discovering her own husband’s double life following his unexpected death. She helps in answering the letter writer’s ultimate question: do I stay and make a life with a man who is not the person I thought I married?

The Past Is Present

Are we doomed to repeat the patterns of our childhood? The Sugars hear from the child of two alcoholics, who cannot tolerate her new boyfriend’s drinking; from a young woman whose partner is reminding her more and more of her emotionally damaged father; and from a daughter who is stuck in a co-dependent relationship with her mentally ill mother.

Grief And Jealousy Collide After An Ex’s Death

The Sugars receive a pained letter from a young woman whose ex-boyfriend was recently murdered in an altercation at a bar. His death came not long after she had cut off communication in an effort to move on. She’s grappling not just with feelings of sorrow and guilt, but jealousy — toward a young woman who came into his life after they’d broken up.

Powerful Women And The Men Who Love Them

In this episode, the Sugars take two questions on the dynamics of gender, power, and love — one from a man and one from a woman. A young man struggles with jealousy when his girlfriend gets a career opportunity he wants for himself, and a woman finds she’s no longer attracted to her husband now that he’s not the breadwinner.

My Best Friend’s Wedding

We revisit an episode about friendship with one of our most beloved Sugar guests — the writer Ann Patchett. In this episode, the Sugars take a question from a young woman whose best friend since childhood is about to get married to a man she’s known for only six months. The two friends are very different, and the letter writer worries that her impulsive, drama-prone friend is rushing into another bad situation.

The Allure Of The Forbidden Crush

The Sugars look at one especially painful form of love: the crush. They take questions from two letter writers struggling with illicit love interests — one from a career-oriented woman who finds herself drawn to her boss, the other from a recently married woman fantasizing about her husband’s younger brother.

Rapid Fire: A Wealthy Sister, An Impatient Girlfriend, An Unshakeable Love

The Sugars are back for another batch of shorter questions and answers. They take on six quick 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 woman still pining after her girlfriend from a decade back.

Looking For The One, Part 3: Reimagining Spinster

The Sugars consider the way forward for their single letter writers. For many of the women they hear from, finding “the one” has become the all-consuming focus of their lives. The anxiety and the reality of their situations makes it hard for otherwise confident, successful women to esteem anything else. The Sugars are joined by the writer Kate Bolick, who suggests a new way of thinking about life as a spinster.

Looking For The One, Part 2: The Reality

The Sugars have been avoiding the most frequently asked question they receive from women: Will I ever find the one? In the first episode, they explored the anxieties around that question. In Part 2, they focus on a particular anxiety that comes up over and over in letters from advice-seekers who have begun to question their past and present relationship decisions — should I settle?

Looking For The One, Part 1: The Anxiety

The Sugars have been avoiding the most frequently asked question they receive: Will I ever find the one? In this first episode on the theme, the Sugars explore the anxieties of the women who write in — I’m happy, I’m successful, everything else in my life is going great. But I can’t find a partner. What’s wrong with me? Will I ever find someone? Is it too late? Lena Dunham joins the conversation with her trademark candor.

Happy One Year Of Sugar

The Sugars look back at some of the most memorable letters of 2015. They check back in on a young gay man who was agonizing over whether to come out to his homophobic family, and a new mother who was struggling with boundaries after her alcoholic father relapsed during his first visit with his granddaughter.

Dear Sugar: Back To The Beginning

The Sugars often tell advice seekers: You have to go back to the beginning to get to the bottom of it. So, as 2016 begins, to mark the first year of Dear Sugar Radio, we’re revisiting the pilot episode where it all began.

Sugar For The Holidays

The Sugars take on some of the big questions of the holiday season. How do we balance the competing demands of families? How do we act like adults when we return to our childhood homes? And, what if we aren’t sure we should return home at all?

Moms Who Hate Motherhood

Motherhood has a near-sacred status in our society. If we dare speak negatively about it, it’s only to say: “Motherhood is hard, but it’s worth it.” But for some mothers, it isn’t. In this episode, the Sugars take on the taboo.

The Weight Of Love

The Sugars explore the fraught relationship between body image and romance. In one letter, a married woman reconsiders her priorities after losing 100 pounds. In another, a young man wants his girlfriend to lose weight, but does not understand why she’s so upset when he broaches the subject.

The Deal Killer

The Sugars are taking Thanksgiving weekend off. We’ll be back next week with a new episode. This week, we revisit an earlier episode — The Deal Killer.

Dear Sugar: Live In Cambridge

The Sugars record the show in front of a live audience at First Parish Church in Harvard Square. Taped on the occasion of Cheryl’s new book of quotes, Brave Enough, the Sugars discuss the importance of quotations in their own lives. The questions come from the audience — from a Harvard grad student who just lost a loved one to suicide to a young person gripped by jealousy in romantic relationships. They are joined on stage by rock star Amanda Palmer.

Letter From An Aching Single Father

The Sugars take a question from a single father who’s just dropped his oldest son off at college. He is seized by feelings of guilt — that his attention was often elsewhere, that he didn’t do enough to prepare his sons for the world. They are joined by the writer Brad Watson, himself divorced with two sons.

Dear Sugar: Do I Follow My Head Or My Heart?

The Sugars get a letter from a young woman who has fallen head over heels in love. She and her boyfriend only met a month ago, but they are already in deep. Everything seems perfect, and yet the letter writer can’t help but wonder if the traumas of her new love’s past are hiding somewhere under the surface, threatening to resurface. The Sugars do something new — and get the letter writer on the phone to speak with her directly about her fears.

Sibling Rivalry

The Sugars take on sibling rivalry. The mother of an only child wonders if she should have another but fears cruelty and conflict between the siblings. And a young man is caught between his parents and his brother, who is refusing to let the family spend time with his son.

Dear Sugar: Is My Husband’s Pot Habit A Problem?

If someone smokes pot multiple times a day, but is still a highly functional partner, parent, and worker — is there a problem? That’s the question to the Sugars from a letter writer whose husband has been a habitual marijuana smoker for years. If it is a problem, she wonders, is it his or hers?

An Experiment In Radical Brevity

The Sugars try something new — answering more questions, more quickly. While they always give their hearts and souls to the letters they receive, some questions are just a little more straightforward. The Sugars take on six quick questions, from siblings discovering incriminating texts on their father’s phone to women reeling from encounters with sociopaths to this single sentence — “what do I do if I can’t stand to stay with him but I can’t stand to leave him either?”

The Wounded Child Within

The Sugars are taking this week off, to focus on answering new letters. We’ll be back next week, but in the meantime, we revisit this conversation about the traumas of our past and their role in our present.

When Bad Things Happen

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 take letters from a visual artist who has just learned he is losing his sight, and from a woman whose life has been transformed by her daughter’s life-threatening condition.

The Infidelity Episodes: Esther Perel

The Sugars exploration of infidelity culminates in Part 3, a conversation with Esther Perel. The relationship therapist is focusing her attention on the subject of infidelity – what it is, why we do it, and what it means to us. They also take a question from a married man who longs for lost intimacy with his wife, while also engaging in multiple affairs on the side.

The Infidelity Episodes: The Betrayers

The Sugars exploration of infidelity continues with Part 2: The Betrayers. They take letters from a desperate wife, whose husband gave her a second chance after an emotional infidelity, only for her to do it again; and from a young mother who has gotten herself tangled up with the next-door neighbor after years of unhappy marriage.

The Infidelity Episodes: The Betrayed

The first in a multi-part exploration of infidelity. In Part 1, the Sugars consider letters from the Betrayed; in Part 2, they’ll consider the Betrayers. They’re also joined by the writer and performer Lauren Weedman, who experienced one of the more nightmarish clichés of infidelity, and tells the story.

Dear Sugar: How Do I Survive The Critics?

Dear Sugar Radio is taking off Labor Day 2015 weekend. We’ll be back next week with new episodes. In the meantime, we’re reposting this episode from March 2015, “How Do I Survive The Critics?” with special guest George Saunders. We thought, going into the new school year, it’s a good time to revisit the topic — how do we handle judgment about our work, even the harshest criticism?

When Life Takes A U-Turn

There are those moments in all of our lives — sudden and radical — when we get spun around and everything feels out of our control. The Sugars take questions from two letter writers who have come to such moments.

The Unmothered Mother

The Sugars take a question from the mother of young twins. Her own mother left when she was two years old, and her stepmother was a controlling and manipulative presence in her life. The letter writer is afraid that these toxic experiences being mothered make her destined to fail as a mother.

Do you have a question for Sugar? Tell us the truest version you can bear to tell. Email dearsugarradio@gmail.com or submit it here.

We also want to know what you think of the podcast!  Please take five minutes and fill out our brief survey.  

Get the podcast

The hosts


Steve Almond had an image of Sugar in his mind — a woman with a troubled past and a slightly reckless tongue. Then he read Cheryl Strayed’s work, and realized she was the real-life Sugar. The rest is history. Now, the two best-selling writers team up as Sugar for the first time.

Steve Almond is the author of “Candyfreak” and, recently, “Against Football: One Fan’s Reluctant Manifesto.” He offers additional advice in WBUR’s Heavy Meddle column. Cheryl Strayed is the author of “Wild,” now a major motion picture, and “Tiny Beautiful Things,” a collection of her essays as Sugar.

The views and opinions expressed in this podcast are solely those of the writers and do not reflect the views of WBUR management or its employees.

Most Popular