Dear Chelsea

Updated: 22 Aug 2025 • 274 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 discuss the problem with men, as well as followups from a caller whose partner’s oversized organ became an issue. * https://www.intimaterose.com/collections/vaginal-dilators  https://www.intimaterose.com/collections/pelvic-wands Pelvic Floor Wand Non-hormonal Vaginal Moisturizers: https://hellobon

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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 nuptial

60 min
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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 fam

57 min
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Chelsea and Catherine do a book roundup, and read a followup about gay underwear. * Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail.com * Executive Producer Catherine Law Edited & Engineered by Brad Dickert * * * * * The views and opinions expressed are solely those of the Podcast author, or individ

11 min
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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 welcom

62 min
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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 sis

56 min
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