2 Bears, 1 Cave with Tom Segura & Bert Kreischer
2 Bears, 1 Cave with Tom Segura & Bert Kreischer
YMH Studios
Mel Robbins Calls Out Bert’s People-Pleasing | 2 Bears, 1 Cave
1 hour 59 minutes Posted Nov 10, 2025 at 1:00 pm.
Intro
What's Your Drink?
College Chaos & Cheating Confessions
Nobody Wants To F**k Up Their Life
FOMO, Stoicism, & The Let Them Theory
Why We Need to Disappoint People
Family Guilt & The Dinner Dilemma
An Awkward Nicole Kidman Kiss & Approval Addiction
ADHD, Dyslexia, & The Volcano Inside
What Could Possibly Go Wrong?
Bert Gets Real
Wired To Change
Opportunity Of A Lifetime
Let Them (And Let Yourself) Learn more about your ad choices. Visit megaphone.fm/adchoices
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1:59:14
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Show notes
Tom will be filming his new stand-up special in Milwaukee at The Riverside Theater on November 14th & 15th! Tickets are still available in Milwaukee for the November 14th show. Go get your tickets now at https://tomsegura.com/tour .
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This week, Bert sits down with the one and only Mel Robbins for a brutally honest, hilarious, and surprisingly deep conversation about anxiety, cheating, parenting, and learning how to “let them.” From wild college confessions to Mel breaking down her Let Them Theory in real time, this episode is half therapy, half comedy, and all chaos.
They cover everything — why Bert can’t stop overexplaining to strangers (and accidentally tried to kiss Nicole Kidman), how ADHD and anxiety shaped both of their lives, and why it’s so hard to stop caring what everyone thinks. Mel opens up about her own journey through debt, dysfunction, and discovery — and Bert realizes maybe, just maybe, he doesn’t have to fix everyone to be happy.
If you’ve ever felt like you’re juggling guilt, stress, and trying to please everyone — this episode will hit home and crack you up at the same time.
2 Bears, 1 Cave Ep. 314
https://tomsegura.com/tour
https://www.bertbertbert.com/tour
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Chapters
01:45:51 - Let Them (And Let Yourself) Learn more about your ad choices. Visit megaphone.fm/adchoices