Uploaded May 2026 | Updated September 2026, 3 weeks ago
This week, I sit down with the one and only Chelsea Handler! And in true Chelsea fashion, nothing is off limits. We get into how she's staying single, getting hotter & giving less f*cks than ever. We dig into why she has zero interest in long-term relationships, the one thing therapy changed about her, and why her 50s are the best years yet. She also opens up about Hollywood, confidence, sex, if sobriety is a dealbreaker, and the freedom that comes with truly knowing yourself. We also talk about her dating life, celebrity disasters, why she loves being alone, and the biggest lessons she’s learned getting older. Chelsea is the best, and I think you guys are going to love this conversation!
00:00 — Surviving Life on a Massive Stand-Up Tour
02:05 — Looking Incredible at 50
04:30 — Why I Only Date Men for Five or Six Months
08:48 — The Freedom of Being Single & Protecting Your Energy
11:37 — The Difference Between Your 30s, 40s, and 50s
17:36 — How Therapy Forced Me to Stop Fixing Everyone's Problems
32:00 — My Stance on Hollywood & Why I Choose Real Life
39:03 — Bad Celebrity Dates
44:44 — Playing "Hot or Not"
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Wayfair: Get prepped for patio season for way less. Head to Wayfair.com right now to shop all things home.
Tonal: Right now, Tonal is offering our listeners $200 off your Tonal purchase with promo code HONEST
Foria: Experience your juiciest and deepest sensual experience with a bottle of Foria. Foria is offering a special deal for our listeners. Get 20% off your first order by visiting foriawellness.com/HONEST OR use code HONEST at checkout.
Produced by Dear Media.
This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct or indirect financial interest in products, or services referred to in this episode.
For more Let’s Be Honest, follow along at:
Instagram: instagram.com/kristincavallari
TikTok: tiktok.com/@kristincavallari
YouTube: youtube.com/channel/UCSJqT36l3imYtr_QF6LFNXA
Produced by Dear Media.
Follow Dear Media:
Listen: dearmedia.com/shows
Instagram: instagram.com/dearmediastudio
TikTok: tiktok.com/@dearmedia
Linkedin: linkedin.com/company/dear-media
Shop Dear Media:
shop.dearmedia.com
ABOUT DEAR MEDIA
Dear Media is the largest podcast network focused on amplifying women’s voices and audiences. Founded in 2018, DM hosts 80+ podcasts fronted by top-tier talent and has a following of more than 60M across social channels. DM is building the podcast incubator of the future through a 360-degree business model, providing unparalleled support from concept to editorial, production, distribution, and commerce extensions. Due to its highly engaged and vast consumer audience, the network attracts global brands and digital savvy partners.
SyncID: MB01HHBEV1K9OGB
This week, I sit down with the one and only Chelsea Handler! And in true Chelsea fashion, nothing is off limits. We get into how she's staying single, getting hotter & giving less f*cks than ever. We dig into why she has zero interest in long-term relationships, the one thing therapy changed about her, and why her 50s are the best years yet. She also opens up about Hollywood, confidence, sex, if sobriety is a dealbreaker, and the freedom that comes with truly knowing yourself. We also talk about her dating life, celebrity disasters, why she loves being alone, and the biggest lessons she’s learned getting older. Chelsea is the best, and I think you guys are going to love this conversation!
00:00 — Surviving Life on a Massive Stand-Up Tour
02:05 — Looking Incredible at 50
04:30 — Why I Only Date Men for Five or Six Months
08:48 — The Freedom of Being Single & Protecting Your Energy
11:37 — The Difference Between Your 30s, 40s, and 50s
17:36 — How Therapy Forced Me to Stop Fixing Everyone's Problems
32:00 — My Stance on Hollywood & Why I Choose Real Life
39:03 — Bad Celebrity Dates
44:44 — Playing "Hot or Not"
Nutrafol: See thicker, stronger, faster-growing hair with less shedding in just 3-6 months with Nutrafol. For a limited time, Nutrafol is offering our listeners $10 off your first month’s subscription and free shipping when you go to Nutrafol.com and enter the promo code HONEST
Wayfair: Get prepped for patio season for way less. Head to Wayfair.com right now to shop all things home.
Tonal: Right now, Tonal is offering our listeners $200 off your Tonal purchase with promo code HONEST
Foria: Experience your juiciest and deepest sensual experience with a bottle of Foria. Foria is offering a special deal for our listeners. Get 20% off your first order by visiting foriawellness.com/HONEST OR use code HONEST at checkout.
Produced by Dear Media.
This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct or indirect financial interest in products, or services referred to in this episode.
For more Let’s Be Honest, follow along at:
Instagram: instagram.com/kristincavallari
TikTok: tiktok.com/@kristincavallari
YouTube: youtube.com/channel/UCSJqT36l3imYtr_QF6LFNXA
Produced by Dear Media.
Follow Dear Media:
Listen: dearmedia.com/shows
Instagram: instagram.com/dearmediastudio
TikTok: tiktok.com/@dearmedia
Linkedin: linkedin.com/company/dear-media
Shop Dear Media:
shop.dearmedia.com
ABOUT DEAR MEDIA
Dear Media is the largest podcast network focused on amplifying women’s voices and audiences. Founded in 2018, DM hosts 80+ podcasts fronted by top-tier talent and has a following of more than 60M across social channels. DM is building the podcast incubator of the future through a 360-degree business model, providing unparalleled support from concept to editorial, production, distribution, and commerce extensions. Due to its highly engaged and vast consumer audience, the network attracts global brands and digital savvy partners.
SyncID: MB01HHBEV1K9OGB
