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

August 6, 2026 66 mins

Madelyn Cline joins Chelsea to discuss the final season of her hit show Outer Banks, the perils of layering sunblock and deet, and the benefits of dating a finance guy. Then: A listener may need to be a little meaner when turning down dates.  A husband’s Youtube fave triggers his wife’s ED.   And a 27-year-old with teenage daughters wonders when she gets to have a life.  

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Chelsea’s personal trainer Ben Bruno is here to discuss dumbbells, getting fit, and why doing things the simple way actually gets you a lot farther.  Sign up for Ben Bruno’s fitness program here!

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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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Tiffany Haddish is here to discuss how dating cops led her to developing discernment, why she once shat in her ex’s shoes, and gives a play-by-play of the Netflix doc Maternal Instinct. Then: A single woman struggles to find a man who’s both interesting and interested.  A surprise pregnancy signals the end of a relationship.  And a divorcee isn’t sure how to fill her life now the chaos is gone. &nbs...

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Yamaneika’s in Chelsea’s house (and won’t leave) to discuss the merits of an Erewhon rotisserie Chicken, the power of two women wrestling, and why Chelsea’s the problem this week.  Then: A family falls apart after an open marriage becomes a little too open.  A trans man’s love life gets increasingly more complicated.  And a sister needs to put her sister in her place. 

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Chelsea and Catherine get an update about a long-distance move for love, and a caller struggles with a marriage that really shouldn’t be long-distance at all.

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Find our callers today on instagram!

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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 ...

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Hannah Gadsby joins Chelsea to chat about the dubious nature of cruises, why their new special features a sock puppet, and how Tasmania is not in Africa. 

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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, an...

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D’Arcy Carden joins Chelsea to chat about eating her niece’s hair, why working on the Handmaid’s Tale was actually fun, and the best advice Ted Danson ever gave her. Then: An actor struggles to know what’s next in the shifting landscape of entertainment.  And a med student must decide between her fiance and the potential of another man.

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Find Cassidi and her new production here

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Chelsea and Catherine hear from a listener who saw the Signs, and a Floridian is looking to get the hell out.

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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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July 2, 2026 58 mins

Wanda Sykes joins Chelsea to talk about what she’d do if Ivanka moved in, treating church like bar-hopping, and why she may not be able to top her new special, LEGACY.  Then: A Black woman cringes when going to her white boyfriend’s redneck family get-togethers. A 50-something is laid off but looking forward to what’s next. And a bisexual man worries his lack of experience will hold him back.

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June 25, 2026 64 mins

The indomitable TS Madison joins Chelsea to discuss the voice that told her she’d be friends with RuPaul, what it means to be a woman, and why she remains well-endowed.  Then: A caller learns that you f*ck young, date rich.  And a childfree woman can’t shake the guys who *might* want kids.  

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

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Executive Producer Catherine Law

E...

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Chelsea and Catherine go on a book roundup filled with giants, sisterhood, and the deep, dark woods. 

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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...

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Internet personality Tana Mongeau joins Chelsea to talk about writing a new chapter for yourself, what happens when a party girl stops drinking, and her new podcast, Brand Safe. Then: A fresh nose job has a transwoman seeking celibacy.  And the hunt for a threesome needs to move out of one caller’s own backyard. 

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

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June 11, 2026 63 mins

Cheri Oteri (Scary Movie 6) is here to chat with Chelsea about the power of a salmon plank, why she left SNL at the right time, and how the former First Lady helped her through her breast cancer diagnosis.  Then: Can you steal a baby name?  A 30-something seeking a burial plot has lost the plot.  And a widow wrestles with a cross-country move after losing her husband.   

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Book Mentions: Near Death in ...

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Chelsea and Catherine discover the origin of the name Ray J and solve geographical conundrums for the polycule. 

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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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Astrophysicist Neil deGrasse Tyson joins Chelsea to talk about what little green men might actually look like, how to prove alien life exists, and disclose what Area 51 is REALLY used for.  

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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 ind...

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Kerri Kenney-Silver (The Four Seasons, Reno 911) joins Chelsea to talk about the many lives she’s led as a frontwoman in a band, an actor and a mom, why Reno 911 is in the Epstein files, and grabbing every opportunity when it came to her.  Then: A new niece has a terrible nickname.  A 30-something investigates her pregnant bestie’s cheating husband.  And a dad is taking his new girlfriend to the cottage a...

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Chelsea and Catherine hear from a season 1-favorite caller, rein in a meddling mom, and cheer a fast followup. 

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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 iHeartMe...

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May 21, 2026 49 mins

The iconic Luenell is back to discuss why all men need therapy, opening a brothel next door to Chelsea’s, and why she can talk about crack in front of her daughter. Then: A wife wonders if she should dose her husband with a little Xanax.  A 30-something is curious about sugaring.  And mom-to-be wonders who to tell when her ex goes awol.  

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Kevin Kane (Law & Order SVU) stops by to discuss NOT having an affair with his now-wife, why he thinks we should bring back (a little) bullying, and why mahjong is the new pickleball.  Then: A tarot reader wants to go full-time.  An auntie wants to escape an escape-room birthday.  And a girlfriend is thrown when she learns her boyfriend slipped into her bestie’s DM’s first. 

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Chelsea and Catherine get a followup from a disgruntled wife and take exclusively one-drink questions. 

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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 i...

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