Dear Chelsea

iHeartPodcasts

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: [email protected]  

  • 11 minutes 50 seconds
    Minisode: Big Boyfriend Problems with Yamaneika Saunders

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

    *

    Need some advice from Chelsea? Email us at [email protected]

    *

    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.

    11 July 2025, 7:05 am
  • 50 minutes
    Reclaiming with Monica Lewinsky

    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 [email protected]

    *

    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.

    10 July 2025, 7:05 am
  • 1 hour 3 minutes
    My D*ck is Exhausted with Boom Boom "Jeff" Hiller

    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 [email protected]

    *

    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.

    3 July 2025, 7:05 am
  • 24 minutes 51 seconds
    “Totally Booked with Zibby: Chelsea Handler”

    Today, we are sharing Chelsea’s recent interview on the Webby Award-winning daily podcast Totally Booked with Zibby. Hosted by Zibby Owens – the powerhouse bookstore owner and bestselling author dubbed "NYC's Most Powerful Book-fluencer" by Vulture – Totally Booked delivers interviews with the best, buzziest, and underrated authors to share work that’s truly worth your time.

     

    In this specific episode, you’ll hear all about Chelsea’s recent New York Times bestselling book I’ll Have What She’s Having, in addition to her takes on relationships, independence and solitude, and handling criticism. She also shares unforgettable life moments – from a transformative encounter with Jane Fonda to skiing in Whistler to an unexpected visit to Kennebunkport, where three edibles helped her keep her cool.

     

    For more episodes, follow Totally Booked with Zibby on Apple Podcasts, Spotify, or wherever you get podcasts. New episodes are released daily!

    See omnystudio.com/listener for privacy information.

    29 June 2025, 7:05 am
  • 15 minutes 14 seconds
    Minisode: I’m Not Here to Tear Up Love with Yamaneika Saunders

    Yamaneika joins Chelsea to discuss some sneakers that need to be retired.  Then: A girlfriend’s support for her boyfriend begins to waver. 

    *

    Need some advice from Chelsea? Email us at [email protected]

    *

    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.

    27 June 2025, 7:05 am
  • 55 minutes 52 seconds
    Friends to Lovers with Sophia Bush

    Sophia Bush is here to talk about her acceptance into the club of Hot Celesbians, takes the reins on how to weather the political landscape, and wonders why nobody noticed she’s been kissing girls onscreen for quite some time.  Then: A FWB situation has a caller dickmatized.  A lesbian is angry about politics - but should she hold back? And a best friend wonders how to tell her bestie she’s in love with her. 

    *

    Need some advice from Chelsea? Email us at [email protected]

    *

    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.

    26 June 2025, 7:05 am
  • 53 minutes 47 seconds
    Scheduling Sex with Atsuko Okatsuka

    Atsuko Okatsuka is back to chat about the time she didn’t do laundry for 7 years, the weirdest things about touring in Europe, and why she’ll never be allowed to get another haircut.  Then: A singer sends inappropriate texts.  A sister-in-law spat needs to be dragged out in the open.  And a burnt-out lawyer hits the breaks.  

    *

    Need some advice from Chelsea? Email us at [email protected]

    *

    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.

    19 June 2025, 7:05 am
  • 13 minutes 4 seconds
    Minisode: Cosby Voice with Yamaneika Saunders

    Yamaneika Saunders joins Chelsea to talk about the worst/best dinner they ever had.  Then: A therapist-cum-psychedelics-dealer gets trolled online by her ex. 

    *

    Need some advice from Chelsea? Email us at [email protected]

    *

    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.

    13 June 2025, 7:05 am
  • 52 minutes 38 seconds
    Folk Magic with Wendi McLendon-Covey

    Wendi McLendon-Covey joins Chelsea to chat about her love of New Orleans, why she’s obsessed with costar David Alan Grier, and the best thing about being childfree by choice. Then: A childfree woman struggles when her partner’s teenage kid moves in with them. A mom wonders if her daughter is asexual.  And a 20-something is put in an awkward position when her neighbor sleeps with her best friend.  

    *

    Need some advice from Chelsea? Email us at [email protected]

    *

    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.

    12 June 2025, 7:05 am
  • 1 hour 3 minutes
    Supercharged Growth with Maren Morris

    Maren Morris dishes with Chelsea about leaving country music and her marriage, supercharging her personal growth, and why being a woman takes guts and balls.  Then: A brand-new singer wonders how to gain confidence. A trans man struggles to find peace with his wife as they divorce. And a wedding RSVP starts to waffle.  

    *

    Need some advice from Chelsea? Email us at [email protected]

    *

    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.

    5 June 2025, 7:05 am
  • 15 minutes 48 seconds
    Minisode: Over-the-Pants with Chelsea + Catherine

    Chelsea and Catherine do couples counseling with a wife whose husband has “penis fingers”. 

    *

    Order a signed copy of Chelsea’s new book HERE!

    *

    Need some advice from Chelsea? Email us at [email protected]

    *

    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.

    30 May 2025, 7:05 am
  • More Episodes? Get the App