Dear Chelsea

iHeartPodcasts
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Jan 8, 2026 • 45min

A Late Bloomer with Kaitlin Olson

Kaitlin Olson (Hacks, High Potential, It’s Always Sunny in Philadelphia) joins Chelsea to chat about juggling 3 shows at once, forcing her husband Rob Mac to fall in love with her, and why balls are funny… until they’re not.   Then: A postal worker can’t jibe with girls her own age and finds happiness in may-december friendships.  An ex-wife struggles to name a newborn.  And an ex-stripper chases her new dream job - but will her past hold her back? * Check out Redneck Kitty at @redneck.kitty * 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 not act or shall refrain from acting based on information contained in the Podcast without first seeking independent medical advice.  See omnystudio.com/listener for privacy information.
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Jan 2, 2026 • 11min

Minisode: Pikachu vs. Kaslapus with Chelsea + Catherine

Chelsea and Catherine get an update from a caller who married his longtime love and assess a friend-zoning situation. * 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 not act or shall refrain from acting based on information contained in the Podcast without first seeking independent medical advice.  See omnystudio.com/listener for privacy information.
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Jan 1, 2026 • 58min

Night Thoughts with Kumail Nanjiani

Kumail Nanjiani (OH MARY!, Night Thoughts) joins Chelsea to talk about building trust in a relationship, surviving the loss of his cat Bagel, and why working out is actually very nerdy.  Then: A doggy deal breaker is just the tip of the iceberg in one man’s troubled relationship.  And tension around tipping leads to an embarrassing situation for a restaurant’s regular.  * 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 not act or shall refrain from acting based on information contained in the Podcast without first seeking independent medical advice.  See omnystudio.com/listener for privacy information.
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Dec 25, 2025 • 51min

Having a Felch with Toni Collette

Actress Toni Collette (Wayward, Goodbye June) joins Chelsea to talk about why Rome is her happy place, what it feels like to get your character wrong, and finding her inner creep for her role as a cult leader.  Then: A baby actor struggles to leave his family to pursue his career.  A stepmom struggles to connect with her stepdaughter after a sibling is born.   And a sister’s tactless behavior results in an awkward confrontation. * 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 not act or shall refrain from acting based on information contained in the Podcast without first seeking independent medical advice.  See omnystudio.com/listener for privacy information.
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Dec 19, 2025 • 12min

Minisode: Snatch That Kid Up with Chelsea + Catherine

Chelsea and Catherine talk with a couple exploring the foster system… for the second time.   * 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 not act or shall refrain from acting based on information contained in the Podcast without first seeking independent medical advice.  See omnystudio.com/listener for privacy information.
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Dec 18, 2025 • 54min

Not a Loser with Amanda Seyfried

Amanda Seyfried (The Housemaid, The Testament of Ann Lee) joins Chelsea to talk about auditioning for Wicked, mucking stalls on her farm in the Catskills, and why she’ll never do a stage play again.  Then: A wedding in Bali threatens to go off the rails when an evil stepmother needs to be disinvited.   And a florist falls in love with an Ecuadorian rose merchant and wrestles with following her head or her heart.  * 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 not act or shall refrain from acting based on information contained in the Podcast without first seeking independent medical advice.  See omnystudio.com/listener for privacy information.
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Dec 11, 2025 • 54min

Tio & Tio with Ross Mathews & Wellinthon Garcia-Mathews

Ross Mathews & Wellinthon Garcia-Mathews are here to talk about RuPaul’s best advice, early bedtimes, and putting a saddle on life.  Then: A drag performer wrestles with a change of heart about their artform.  A 30-something wants his firefighter boyfriend to open up. And a year-long relationship gets put back in the closet when one woman struggles to tell her family she has a girlfriend.  * Pick up your copy of Tio & Tio in English or en Español! * 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 not act or shall refrain from acting based on information contained in the Podcast without first seeking independent medical advice.  See omnystudio.com/listener for privacy information.
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Dec 5, 2025 • 58min

Put Some Luxury On It with Da’Vine Joy Randolph

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 corporate drone is desperate to get out of the office and into the great outdoors. And a May-December relationship is nearing its end… just not nearly fast enough.  * 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 not act or shall refrain from acting based on information contained in the Podcast without first seeking independent medical advice.  See omnystudio.com/listener for privacy information.
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Dec 4, 2025 • 58min

Swimming Naked with Elizabeth Olsen

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 lawyer can’t get her man to commit - so she’s stuck paying double rent.  * 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 not act or shall refrain from acting based on information contained in the Podcast without first seeking independent medical advice.  See omnystudio.com/listener for privacy information.
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Nov 28, 2025 • 13min

Minisode: Type Ho Positive with Chelsea + Catherine

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 * * * 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 not act or shall refrain from acting based on information contained in the Podcast without first seeking independent medical advice.  See omnystudio.com/listener for privacy information.

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