Mel Robbins Calls Out Bert’s People-Pleasing 2 Bears, 1 Cave

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 . SPONSORS: -Take advantage of Ridge’s Biggest Sale of the Year and GET UP TO 47% Off by going to -Get $10 Off @‌BRUNT with code CAVE at -Give the gift of smooth this holiday season with the Performance Package 5.0 Ultra. Get 15% off + free shipping at with code BEARS. -Order a bottle of Por Osos and some killer merch online 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 Chapters 00:00:00 - Intro 00:00:46 - What's Your Drink? 00:03:50 - College Chaos & Cheating Confessions 00:13:47 - Nobody Wants To F**k Up Their Life 00:23:12 - FOMO, Stoicism, & The Let Them Theory 00:34:42 - Why We Need to Disappoint People 00:47:55 - Family Guilt & The Dinner Dilemma 00:55:08 - An Awkward Nicole Kidman Kiss & Approval Addiction 01:01:39 - ADHD, Dyslexia, & The Volcano Inside 01:10:44 - What Could Possibly Go Wrong? 01:20:01 - Bert Gets Real 01:31:05 - Wired To Change 01:36:25 - Opportunity Of A Lifetime 01:45:51 - Let Them (And Let Yourself) Learn more about your ad choices. Visit megaphone.fm/adchoices

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Mel Robbins Calls Out Bert’s People-Pleasing 2 Bears, 1 Cave is an episode from 2 Bears 1 Cave with Tom Segura & Bert Kreischer by 2 Bears 1 Cave.

This episode is 119:14 long.

This episode was published on Nov 10, 2025.

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