Dear Chelsea

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Latest Episodes:

The Psychology of Your 20s with Jemma Sbeg Aug 14, 2025

Show notes

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 family’s oscar-worthy goodbyes.

Pick up a copy of Jemma’s book Person in Progress!

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 individuals participating in the Podcast, and do not represent the opinions of iHeartMedia or its employees. This Podcast should not be used as medical advice, mental health advice, mental health counseling or therapy, or as imparting any health care recommendations at all. Individuals are advised to seek independent medical, counseling advice and/or therapy from a competent health care professional with respect to any medical condition, mental health issues, health inquiry or matter, including matters discussed on this Podcast. Guests and listeners should not rely on matters discussed in the Podcast and shall notact or shall refrain from acting based on information contained in the Podcast without first seeking independent medical advice.

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Minisode: Refresh My Memory with Chelsea + Catherine Aug 08, 2025

Show notes

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

See omnystudio.com/listener for privacy information.

The Gayest Olympics with Adam Rippon Aug 07, 2025

Show notes

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 welcome.

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

Executive Producer Catherine Law

Edited & Engineered by Brad Dickert

See omnystudio.com/listener for privacy information.

Crackers with Yamaneika Saunders Jul 31, 2025

Show notes

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 sister’s bitcoin scams.

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

Executive Producer Catherine Law

Edited & Engineered by Brad Dickert

See omnystudio.com/listener for privacy information.

Minisode: Beat It! with Yamaneika Saunders Jul 25, 2025

Show notes

A followup about an 0nlyfans mishap. Then: A book club is threatened by political divides.

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

Executive Producer Catherine Law

Edited & Engineered by Brad Dickert

See omnystudio.com/listener for privacy information.

Outsmarting Kangaroos with Eric Bana Jul 24, 2025

Show notes

Eric Bana is here in America to talk about fighting a kangaroo, his love of fast cars and motorcycles, and why his kids still speak to him. Then: A put-together woman struggles with the decision to leave her lackadaisical husband. And a bisexual man finds out he may be a dad – after a fling 8 years ago.

Want to help James with medical bills? Click here to donate!

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

Executive Producer Catherine Law

Edited & Engineered by Brad Dickert

See omnystudio.com/listener for privacy information.

The Hunting Wives with Malin Akerman Jul 17, 2025

Show notes

Malin Akerman is here to talk about the power of women, why you’ll never win an argument with a narcissist, and why much-younger men make surprisingly great husbands. Then: A 20-something can’t stomach her influencer friend’s lifestyle. A sister wonders how to stay in touch when she makes a cross-country move. And a dad struggles to deal with his kid’s mom - especially when she tells lies about him.

Want to help families impacted by ICE? Follow the links below:

Immigrant Defenders Law Center

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

Executive Producer Catherine Law

Edited & Engineered by Brad Dickert

See omnystudio.com/listener for privacy information.

Minisode: Big Boyfriend Problems with Yamaneika Saunders Jul 11, 2025

Show notes

A positive update from a favorite trans caller. Then: A new boyfriend’s nether-regions overwhelm.

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

Executive Producer Catherine Law

Edited & Engineered by Brad Dickert

See omnystudio.com/listener for privacy information.

Reclaiming with Monica Lewinsky Jul 10, 2025

Show notes

Monica Lewinsky joins Chelsea to talk about the perfect temperature for sleeping, getting better about road rage, and why you should never answer the door naked. Then: A friend is ghosted for having a baby. A government worker struggles with the precarious future of her job. And a gay man loses his mom, his dog and his relationship in one fell swoop… but can he see the light again?

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

Executive Producer Catherine Law

Edited & Engineered by Brad Dickert

See omnystudio.com/listener for privacy information.

My D*ck is Exhausted with Boom Boom "Jeff" Hiller Jul 03, 2025

Show notes

Jeff Hiller joins Chelsea in NY to talk about finally booking the role that launched him, why casting directors love to give you a soft ghost, and the *one* little problem that kept him from becoming a pastor. Then: A couple wonder if they should be opening up or breaking up. A gay son wants to get his mom to stop pushing her religious agenda on him. And a daughter struggles when her mom gets remarried to her Uncle Daddy.

Pick up Jeff’s book Actress of a Certain Age here!

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

Executive Producer Catherine Law

Edited & Engineered by Brad Dickert

See omnystudio.com/listener for privacy information.