Dear Chelsea

Updated: 28 Nov 2025 • 298 episodes
www.iheart.com/podcast/1119-dear-chelsea-81449817

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  

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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.  * Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail.com * Executive Producer Catherine Law Edited & Engineered by Brad Dickert *

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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 com

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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 problem

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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. * Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail.com * Executive Producer Catherine La

12 min
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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

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Haley Lu Richardson (White Lotus) joins Chelsea to talk about her bedside-table collection of “besties”, the text that got her a B- from her therapist, and the breakup that helped her grow the most. Then: A newly-relocated caller debates whether to date on the apps.  And an office romance goes awry.  * Get your copy of

62 min
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