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

February 5, 2026 59 mins

Scotty James joins Chelsea to talk about why his wife is the CEO of his life, his longtime rivalry and friendship with Shaun White, and argue about why snowboarders are just *cooler*.  Then: An expat in Greece needs to have a money conversation with her new man… but is it too soon? A skier wonders if she should transition to snowboarding.  And a wife-turned-Instagram Girlfriend has lost her love for the slopes.

&nb...

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Chelsea and Catherine get an update about a husband’s sexting ways, and a 20-something wants a baby… but is she ready?

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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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January 29, 2026 48 mins

Josh Radnor joins Chelsea to talk about the highs and lows of playing one character for a decade, the delights of NYC, and his sober-curious lifestyle.

Then: A newlywed discovers an attempt at cheating while snooping on her husband’s phone.  A sister wonders if she’s third-wheeling with her brother and his girlfriend. And an employee wants to do her job and make out with her boss.  Just a little bit. 

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N...

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January 22, 2026 57 mins

Emilia Clarke joins Chelsea to chat about learning Russian, her road to recovery after two brain hemorrhages, and how to pretend a tennis ball is a dragon. Then: An Argentinean’s messy habits have his boyfriend busy doing cleanup. A girlfriend is crazy about her new guy, but wants to maintain her single identity.  And a newly-sober caller is comedy-curious.

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

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Chelsea and Catherine get a long-term update from a polygamist’s sister, and a couple calls in precisely because they have no problems.

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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...

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January 15, 2026 60 mins

Drag superstar Monét X Change joining Chelsea to talk about the best party drugs, the scourge of bunions, and everyone’s favorite subject: boofing.  Then: A listener’s inheritance has everyone passing by with their hand out.  A deadbeat dad wins the lottery.  And a friend of Monét’s needs advice on their out-of-drag career.

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

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January 8, 2026 44 mins

Kaitlin Olson (Hacks, High Potential, It’s Always Sunny in Philadelphia) joins Chelsea to chat about juggling 3 shows at once, forcing her husband Rob Mac to fall in love with her, and why balls are funny… until they’re not.  

Then: A postal worker can’t jibe with girls her own age and finds happiness in may-december friendships.  An ex-wife struggles to name a newborn.  And an ex-stripp...

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Chelsea and Catherine get an update from a caller who married his longtime love and assess a friend-zoning situation.

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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 iHeartM...

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January 1, 2026 57 mins

Kumail Nanjiani (OH MARY!, Night Thoughts) joins Chelsea to talk about building trust in a relationship, surviving the loss of his cat Bagel, and why working out is actually very nerdy.  Then: A doggy deal breaker is just the tip of the iceberg in one man’s troubled relationship.  And tension around tipping leads to an embarrassing situation for a restaurant’s regular. 

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Need some advice from Chelsea? Em...

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December 25, 2025 51 mins

Actress Toni Collette (Wayward, Goodbye June) joins Chelsea to talk about why Rome is her happy place, what it feels like to get your character wrong, and finding her inner creep for her role as a cult leader.  Then: A baby actor struggles to leave his family to pursue his career.  A stepmom struggles to connect with her stepdaughter after a sibling is born.   And a sister’s tactless behavior results in an awkw...

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Chelsea and Catherine talk with a couple exploring the foster system… for the second time.  

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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 ...

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December 18, 2025 53 mins

Amanda Seyfried (The Housemaid, The Testament of Ann Lee) joins Chelsea to talk about auditioning for Wicked, mucking stalls on her farm in the Catskills, and why she’ll never do a stage play again.  Then: A wedding in Bali threatens to go off the rails when an evil stepmother needs to be disinvited.  

And a florist falls in love with an Ecuadorian rose merchant and wrestles with following her head or her heart...

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Ross Mathews & Wellinthon Garcia-Mathews are here to talk about RuPaul’s best advice, early bedtimes, and putting a saddle on life.  Then: A drag performer wrestles with a change of heart about their artform.  A 30-something wants his firefighter boyfriend to open up. And a year-long relationship gets put back in the closet when one woman struggles to tell her family she has a girlfriend. 

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Pick up your co...

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Oscar-winner Da’Vine Joy Randolph joins Chelsea to discuss the tea on Shakespeare, how to develope emotional fortitude early, and why she’ll never bring a man onto the red carpet.  Then: The girls break up no fewer than two engagements.  A traveler gets dumped by his boyfriend just before their European getaway. A corporate drone is desperate to get out of the office and into the great outdoors. And a May-Dece...

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December 4, 2025 58 mins

Elizabeth Olsen joins Chelsea to chat about why she swims naked every morning, her thoughts on reincarnation, and why she’s the perfect woman for a man with a fish pic in his bio.  Then: A guncle wants to help his niece steer clear of becoming a Mean Girl.  A single mom struggles to connect on the apps.  And a young lawyer can’t get her man to commit - so she’s stuck paying double rent. 

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Need...

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Chelsea and Catherine get an update from a caller whose bestie is about to be barefoot and pregnant. Then: A boyfriend struggles with asking his partner to open things up. 

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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 ...

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November 27, 2025 60 mins

The Daily Show’s Roy Wood Jr. joins Chelsea to talk about the life lessons he learned from unexpected people, why nobody wants to do you a favor unless they have an ulterior motive, and debate whether his parents had an open marriage way before it was cool. Then: A 40+ standup wonders where to focus her time. And a comedy-adjacent New Yorker tries not to become a Chuckle F*cker. 

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Pick up a copy of The Man of Many Fathe...

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November 20, 2025 55 mins

Mountain Climber Emily Harrington is here to talk about being the first woman to summit El Cap in a day along the Golden Gate route, the mental fortitude it takes to be an endurance athlete, and how to meet a man on Everest. Then: A nosy sister wants to intervene when her brother and his wife are having marital problems… that she’s not supposed to know about. A divorcee searches for the best slopes now that she’s...

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Chelsea and Catherine get a followup from a baby mama who fell out of love… and follows her heart into a whirlwind engagement with a small-town boy. And a couple chooses to live apart after their kids don’t mesh.

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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 t...

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November 13, 2025 55 mins

Isla Fisher joins Chelsea to talk about relying on friendships with women after divorce, ignoring her kids from the bathtub, and how Chelsea lost a closetful of Stella McCartney clothes.  Then: A mom dreads the boring parents at a play-date. A sister wants to parent her brother’s out-of-control kids. And a caller takes umbrage with her sister’s treatment, but Chelsea + Isla disagree on a plan of action.

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Need some...

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