Dear Chelsea

Updated: 05 Dec 2025 • 299 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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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 corp

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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 la

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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

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