Dear Chelsea

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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Every guest on Dear Chelsea

211 guests, ranked by how many people never want them back.

1. —
   Laura Wasser

   How Do I Put This… with Laura Wasser · May 2021

   0 votes

   Never again
2. —
   Leslie Bibb

   A Very Different Vacation with Leslie Bibb · Mar 2025

   0 votes

   Never again
3. —
   Lindsey Vonn

   There Is No Fairy Tale with Lindsey Vonn · Apr 2023

   0 votes

   Never again
4. —
   Lo Bosworth

   The Gut-Vagina Connection with Lo Bosworth · Jan 2025

   0 votes

   Never again
5. —
   Madelaine Petsch

   It’s Me or The Dog with Madelaine Petsch · Oct 2025

   0 votes

   Never again
6. —
   Malin Akerman

   The Hunting Wives with Malin Akerman · Jul 2025

   0 votes

   Never again
7. —
   Marie Faustin

   Minisode: Bringing Delusion To The Table with Aminah Imani, Sydnee Washington, and Marie Faustin · 3 episodes

   0 votes

   Never again
8. —
   Martha Plimpton

   Outta My House with Martha Plimpton · Oct 2025

   0 votes

   Never again
9. —
   Martha Stewart

   TMI with Martha Stewart · Jul 2022

   0 votes

   Never again
10. —
    Mary Elizabeth Ellis

    One Long Muscle with Mary Elizabeth Ellis · Apr 2026

    0 votes

    Never again
11. —
    Matteo Lane

    Meeting Men at Airports with Matteo Lane · 2 episodes

    0 votes

    Never again
12. —
    Mena Suvari

    Does Everybody Have a Secret Sibling? with Mena Suvari · Nov 2021

    0 votes

    Never again
13. —
    Michael Urie

    Fanilow to Ambassilow with Michael Urie · Aug 2025

    0 votes

    Never again
14. —
    Michelle Monaghan

    Enduring Friendships with Michelle Monaghan · Apr 2025

    0 votes

    Never again
15. —
    Mikie Sherrill

    Minisode: Fighting Back with Mikie Sherrill · Oct 2025

    0 votes

    Never again
16. —
    Minnie Driver

    How Much Sunshine Are You Spreading? With Minnie Driver · Jan 2022

    0 votes

    Never again
17. —
    Mitch Albom

    Twice with Mitch Albom · Oct 2025

    0 votes

    Never again
18. —
    Monica Padman

    Here to Meet Men with Monica Padman · Aug 2022

    0 votes

    Never again
19. —
    Naomi Watts

    Vag of Honor with Naomi Watts · Feb 2025

    0 votes

    Never again
20. —
    Nicholas Sparks

    Nick & Night with Nicholas Sparks · Oct 2025

    0 votes

    Never again
21. —
    Nicole Avant

    Think You’ll Be Happy with Nicole Avant · Feb 2024

    0 votes

    Never again
22. —
    Olympian Scotty James

    The Problem with Snowboarders with Olympian Scotty James · Feb 2026

    0 votes

    Never again
23. —
    Paige DeSorbo

    How to Giggle with Hannah Berner + Paige DeSorbo · Apr 2025

    0 votes

    Never again
24. —
    Rachel Morrison

    The Fire Inside with Rachel Morrison · Dec 2024

    0 votes

    Never again
25. —
    Reality Winner

    I Am Not Your Enemy with Whistleblower Reality Winner · Sep 2025

    0 votes

    Never again
26. —
    Riley Keough

    Into The Great Unknown with Riley Keough · Dec 2024

    0 votes

    Never again
27. —
    Ross Mathews

    REPLAY: Kinky Bottoms with Ross Mathews · 2 episodes

    0 votes

    Never again
28. —
    Ruby Warrington

    Women Without Kids with Ruby Warrington · Oct 2023

    0 votes

    Never again
29. —
    Rufus Wainwright

    Dream Requiem with Rufus Wainwright · Apr 2025

    0 votes

    Never again
30. —
    Samantha Irby

    Lean Into the Rot with Samantha Irby · Oct 2023

    0 votes

    Never again
31. —
    Sarah Chalke

    Aggressive Politeness with Sarah Chalke · Mar 2026

    0 votes

    Never again
32. —
    Sarah Shahi

    Life is Lifey with Sarah Shahi · Feb 2026

    0 votes

    Never again
33. —
    Schuyler Bailar

    He/She/They with Schuyler Bailar · Nov 2023

    0 votes

    Never again
34. —
    Sharon Brous

    Victims, Heroes & Learners with Rabbi Sharon Brous · Feb 2024

    0 votes

    Never again
35. —
    Shelly Tygielski

    Taking Your Own Advice with Shelly Tygielski · Oct 2021

    0 votes

    Never again
36. —
    TS Madison

    Can You Spell Shenis? with TS Madison · Jun 2026

    0 votes

    Never again
37. —
    Tana Mongeau

    Hole Out, But Classy with Tana Mongeau · Jun 2026

    0 votes

    Never again
38. —
    Therapist Lori Gottlieb

    Canaries in Coal Mines with Therapist Lori Gottlieb · Dec 2021

    0 votes

    Never again
39. —
    Therapist Nedra Tawwab

    Family Secrets with Therapist Nedra Tawwab · Oct 2024

    0 votes

    Never again
40. —
    Tiffani Thiessen

    Dad's New Girlfriend with Tiffani Thiessen · Dec 2023

    0 votes

    Never again