Tender advice for complicated hearts.
Dear Sugars treats advice as a form of patient attention. Cheryl Strayed and Steve Almond read letters closely, then follow the hidden question beneath sex, aging, parenting, romance, pets, body image, and doubt.
PRESS PLAY
Dear Sugars is an advice show shaped by letters from the lost, lonely, heart-sick, and uncertain. It is intimate without being precious. Cheryl Strayed and Steve Almond read each problem as both a practical situation and a small piece of emotional literature. They listen for what the writer is asking, and for what the writer may not yet be able to ask. The show returns often to love under pressure. Sex changes with age. Desire goes uneven. Parenting can feel unbearable. Bodies carry shame into romance. Pets become part of the household’s moral weather. Partners wonder whether to stay, leave, forgive, speak, or finally admit what is no longer working. Dear Sugars does not rush those questions toward tidy certainty. It lets the ache remain visible. The advice can be direct, especially when a letter points toward self-deception, resentment, or avoidant silence. But the show’s temperament is generous. It treats confusion as something worthy of care, not contempt. Some episodes bring in other voices on self-trust, sexless relationships, pet dilemmas, and parenting regret. Those conversations expand the episode rather than turning it into a standard expert interview. The central ritual remains the same: a letter is read, examined, reframed, and answered with a mix of memoir, moral clarity, and emotional patience. The result is advice that feels less like instruction and more like accompaniment. Dear Sugars suits listeners who want language for what has felt private, shameful, or too complicated to say plainly.
Made for: For listeners drawn to emotionally literate advice about relationships, family, desire, self-trust, and the private doubts people rarely say cleanly. It especially suits those who prefer reflective conversation over quick fixes.
What sets it apart: Dear Sugars stands apart by treating each listener letter as a text to be read carefully, not just a problem to solve. Its strength is the combination of warmth, personal disclosure, moral seriousness, and a readiness to reframe the question beneath the question.
A podcast that fields all your questions and offers radical empathy in return.
Based on 6 episodes we listened to · September 2026
Cheryl Strayed and Steve Almond turn intimate listener dilemmas into patient, practical thinking about love, obligation, bodies, work, and self-trust.
Dear Sugars turns listener letters into careful conversations about the bargains people make with partners, families, work, bodies, and themselves.
A pet custody dispute becomes a mirror, and somehow your own human mess looks clearer.
Press play if you want
Short reviews from the PlayNext desk, based on the episodes we processed.
A frank look at sex after 50, where desire, shame, and fear of loss stay intertwined.
Dear Sugars treats sex after 50 as a serious emotional subject rather than a punchline or a fading afterthought. It draws on listener letters from people in their 50s, 60s, 70s and beyond, and keeps circling one plain idea: bodies age, but desire and erotic life do not simply…
A tender look at parenting guilt, change, and the work of forgiving yourself.
Steve Allman and Cheryl Strayed treat change as something people move through, not something they simply announce. One voice circles intentions, a long family trip, and the odd way another person's wonder can be felt as bitterness.
A patient conversation about self-trust that stays grounded in lived experience.
The episode turns a listener's question into a plain-spoken case for self-trust. Cheryl Strayed and Steve Almond frame the work as learning to be your own guide after books, therapists, and friends have had their say.
Pet love becomes a clear-eyed lesson in labor, boundaries, and tenderness.
Dear Sugars treats pet care as more than a personal headache. It becomes a study of work, limits, and the quiet pressure that sets in when affection runs up against what can be sustained.
A frank, tender look at how body shame can complicate love and desire.
Dear Sugars centers this conversation on body weight and romance, using a listener letter to ask who gets to feel desirable, who gets to feel chosen, and how shame can complicate both loving and being loved.
A thoughtful talk about love, work, and selfhood.
Dear Sugar Radio treats a love story as more than a question of affection, showing how career can ask for an equal claim. Two listener letters are handled with patience, and Cheryl Strayed and Steve Almond slow the issue down enough to see the choice under the surface: how…
Desire does not retire.
Change starts with a hard look.
This episode of Dear Sugar Radio features hosts Cheryl Strayed and Steve Almond answering listener letters in a rapid-fire format focused on the theme of whether to stay in or leave various situations in life.
A lost heart is looking for its own compass.
Pets become the pressure point.
Steve and Cheryl begin with body weight and romance.
Cheryl Strayed and Steve Almond host a rapid-fire Dear Sugar Radio episode offering advice on love and doubt, starting with a letter about a woman questioning her relationship despite positive signs.
This episode of Dear Sugars revisits the topic of sexless relationships, specifically addressing the perspective of the partner who feels pressured for sex, in response to listener feedback from a previous episode.
A person struggles with whether to build a fence around their property due to neighborhood kids freely entering their messy backyard, conflicting with their ethos of openness versus practical boundaries.
The hosts discuss spending addictions with guest Buzz Bissinger, exploring the serious consequences and personal struggles behind compulsive shopping.
The hosts discuss letters from older listeners about sex and desire, challenging cultural norms around aging and eroticism.
The hosts discuss privilege and systemic oppression, responding to listener letters with radical empathy.
Host Shirley Leung shares her breast cancer diagnosis and treatment journey, exploring the emotional toll and the decision to go public.
Love arrives with a but.
This episode features a therapy session where a client uses ketamine to heal from childhood abuse and betrayal by social workers.
This episode is a live recording of the Dear Sugars podcast's summer party event hosted by Steve Allman and Cheryl Strayed.
The hosts discuss the modern phenomenon of ghosting, exploring its origins in digital communication and its impact on relationships.
A friend's story about his young son completely rejecting him after a divorce, refusing contact and even referring to him as 'it', leaving the father devastated.
A listener seeks advice on how to help her husband understand the emotional labor involved in managing household and family responsibilities without sounding like she's complaining.
A person shares their 25-year struggle with dieting, body image, and self-worth, expressing exhaustion and a desire for acceptance.
The hosts discuss listener letters about sex and intimacy among older adults, offering empathetic advice.
The hosts introduce a rapid-fire segment on love and money, drawing on literary examples to explore the intersection of romantic and economic anxiety.
A woman seeks advice on whether to pursue a deep connection with a man from a traumatic background despite her own stable upbringing.
The hosts introduce a rapid-fire segment and address a listener's frustration about being stuck watching in-laws' kids during vacation.
The hosts answer listener questions about love and money, using literary references to explore the intersection of romantic and economic anxiety.
The hosts discuss a listener's letter about learning to trust oneself after seeking external advice, exploring what it means to follow one's own heart.
The episode opens with a humorous ad segment before transitioning into the show's signature advice-giving format, where hosts offer empathetic responses to listener questions.
The hosts respond to listener feedback on a previous episode, discussing missed perspectives and offering empathetic advice.
The hosts introduce a two-part episode exploring the experience of living with grief after a child's death, focusing on the perspectives of parents and siblings.
Hosts Cheryl Strayed and Steve Almond discuss listener letters and offer empathetic advice on personal struggles.
The hosts introduce a listener's story about a friend's son rejecting his father after a divorce, exploring themes of family estrangement and emotional pain.
A guest-hosted episode exploring how couples navigate financial differences and compromise in romantic partnerships.
The hosts introduce the show and recall how Cheryl Strayed took over the Dear Sugar column.
The hosts discuss how to live in the shadow of a damaged parent and find a way out of that shadow.
The episode opens with a letter from a young mother of five seeking advice, framed by the hosts' promise of radical empathy.