Dear Chelsea

Dear Chelsea

On this weekly advice show, comedian & author Chelsea Handler answers listener questions with the hilarious edge you know her for. Joined each week by co-host Catherine Law and celebrity guests, Chelsea never shies away from giving her honest opinion on everything from love, sex and weed to family issues or losing a loved one. Every episode takes you on a ride from funny and informative to inspirational and heartbreaking – and back again. Do you need advice from Chelsea? Send us your question at: DearChelseaPodcast@gmail.com

Episodes

October 3, 2025 16 mins

Chelsea and Catherine figure out how to survive AI, and a caller wonders if she should fake an acid trip. 

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Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail.com

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Executive Producer Catherine Law

Edited & Engineered by Brad Dickert

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The views and opinions expressed are solely those of the Podcast author, or individuals participating in the Podcast, and do not represent the opinions of iHeartMedia o...

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Judy Greer joins Chelsea to chat about the time she got fired from a movie set, why step-parenting is the clutch job, and why you don’t get weekends off when you date the good dad.  Then: An Angeleno realizes she’s accidentally dating a MAGAt.  And a young mom struggles in her marriage when her wife’s unemployment seems neverending. 

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Gratitude Journal Prompts

Journal apps:

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September 25, 2025 56 mins

Zosia Mamet joins Chelsea to talk about surviving an eating disorder, the time Nyquil-induced hallucinations almost got her fired from Girls, and why being a nepito baby isn’t all it’s cracked up to be. Then: A Chicagoan wonders if he should give up his pastime as a comment warrior.  And a soon-to-be-groom has reservations about inviting his mother to the wedding.

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Need some advice from Chelsea? Email us at DearCh...

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Chelsea and Catherine get a Friends-with-Benefits followup and hear from a mother-daughter-duo who inspire stalkers. 

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Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail.com

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Executive Producer Catherine Law

Edited & Engineered by Brad Dickert

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The views and opinions expressed are solely those of the Podcast author, or individuals participating in the Podcast, and do not represent the opinions of iH...

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Chelsea is joined today by whistleblower Reality Winner, a former linguist and intelligence analyst, arrested in 2017 for leaking classified documents  about Russian interference in the 2016 election.  They discuss Reality’s arrest, incarceration and recovery - and why it’s so important to speak out when you see injustice.  

 

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Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail...

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September 11, 2025 60 mins

Debbie Gibson joins Chelsea in-studio to talk about the one that got away, when teenage girls know more than men in suits, and what life is like in her second act. Then: Menopause has a divorcee feeling down.  A 30-something and her bestie beef with judgmental parents.  And a grieving daughter wants to get her life back. 

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Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail.com

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Executive Producer C...

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Chelsea and Catherine learn about the need for a new vocab segment, a son wants his mom to move in, and an auntie gets caught playing favorites.  

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Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail.com

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Executive Producer Catherine Law

Edited & Engineered by Brad Dickert

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The views and opinions expressed are solely those of the Podcast author, or individuals participating in the Podcast, and d...

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September 4, 2025 62 mins

Comic Sam Morril is in the NY studio to discuss the problem with dating younger people, tormenting morning news hosts, and why a rec center is his home away from home.  Then: Soon-Yi confusion ensues as a daughter struggles to accept her dad’s romantic escapades. 

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Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail.com

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Executive Producer Catherine Law

Edited & Engineered by Brad Dickert

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August 28, 2025 67 mins

The iconic Kathy Griffin joins Chelsea to have a frank talk about facelifts, spontaneous combustion, and the photo that got her canceled.  Then: A busy professional is ready to build new relationships after friends’ passing. And a 34-year-old is ready to retire… or maybe marry Kathy? 

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Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail.com

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Executive Producer Catherine Law

Edited & Engi...

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Chelsea and Catherine discuss the problem with men, as well as followups from a caller whose partner’s oversized organ became an issue.

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https://www.intimaterose.com/collections/vaginal-dilators 

https://www.intimaterose.com/collections/pelvic-wands

Pelvic Floor Wand

Non-hormonal Vaginal Moisturizers:

https://hellobonafide.com/products/revaree-plus 

https://hyalogyn.com/ 

https://goodcleanlove.com/collections/...

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August 21, 2025 60 mins

Shrinking’s Michael Urie joins Chelsea to discuss what it’s like joining the cast of OH MARY! while reveling in his first Emmy nomination, building a mall in your basement, and everything you need to know about the Male Barbra Streisand.  And the female one.  Then: A UK-dwelling sister begs to skip her sister’s nuptials. A friend rebels against a pathological liar.  And a man struggles to stay in a ...

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Jemma Sbeg joins Chelsea to talk about age-gap friendships, how life is a series of waiting rooms, and why friendship breakups can be as awful as romantic breakups.  Then: A newly queer woman wonders if she should move to a larger city to surround herself with community.  A long-distance daughter struggles with her family’s oscar-worthy goodbyes.  

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Pick up a copy of Jemma’s book Person in Progress!

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Chelsea and Catherine do a book roundup, and read a followup about gay underwear.

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Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail.com

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Executive Producer Catherine Law

Edited & Engineered by Brad Dickert

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The views and opinions expressed are solely those of the Podcast author, or individuals participating in the Podcast, and do not represent the opinions of iHeartMedia or its employees.  Thi...

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August 7, 2025 62 mins

Olympic phenom Adam Rippon is here to talk about the gayest Olympics, beefing with the Vice President, and the juiciest ice skating scandals of the 90s. Then: A lesbian throuple works through pangs of jealousy.  A dog mom is bereft when her pooch prefers its papa.  And an Ashley Madison hookup has overstayed its welcome.

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Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail.com

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Executive Producer Catheri...

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July 31, 2025 56 mins

Yamaneika Saunders is back for a full episode, this time to talk about perimenopause, why Chelsea sent her a box of vibrators, and bringing a buddy to a mammogram.  Then: A mom is concerned she’s smoking too much weed while caring for her toddler.  A youngest sister finds herself cleaning up the messes of her older sister’s bitcoin scams.  

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Need some advice from Chelsea? Email us at DearChelseaPodc...

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A followup about an 0nlyfans mishap.  Then: A book club is threatened by political divides.

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Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail.com

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Executive Producer Catherine Law

Edited & Engineered by Brad Dickert

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The views and opinions expressed are solely those of the Podcast author, or individuals participating in the Podcast, and do not represent the opinions of iHeartMedia or its emplo...

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July 24, 2025 58 mins

Eric Bana is here in America to talk about fighting a kangaroo, his love of fast cars and motorcycles, and why his kids still speak to him.  Then: A put-together woman struggles with the decision to leave her lackadaisical husband.  And a bisexual man finds out he may be a dad – after a fling 8 years ago.  

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Want to help James with medical bills? Click here to donate! 

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Need some advice from Chelsea...

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July 17, 2025 60 mins

Malin Akerman is here to talk about the power of women, why you’ll never win an argument with a narcissist, and why much-younger men make surprisingly great husbands. Then: A 20-something can’t stomach her influencer friend’s lifestyle. A sister wonders how to stay in touch when she makes a cross-country move.  And a dad struggles to deal with his kid’s mom - especially when she tells lies about him.&nb...

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A positive update from a favorite trans caller.  Then: A new boyfriend’s nether-regions overwhelm.   

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Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail.com

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Executive Producer Catherine Law

Edited & Engineered by Brad Dickert

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The views and opinions expressed are solely those of the Podcast author, or individuals participating in the Podcast, and do not represent the opini...

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July 10, 2025 50 mins

Monica Lewinsky joins Chelsea to talk about the perfect temperature for sleeping, getting better about road rage, and why you should never answer the door naked.  Then: A friend is ghosted for having a baby.  A government worker struggles with the precarious future of her job.  And a gay man loses his mom, his dog and his relationship in one fell swoop… but can he see the light again?

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Need some advice from C...

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