Awkward Moments Episodes

32
Aug. 14, 2025

Brad Pitt, Glenn Close, and Tony Danza Walk Into a Podcast: Our Most Awkward Celebrity Moments

From Brad Pitt’s jewel-inlaid cowboy boots to Jennifer Aniston playfully balancing toward a stranger on a hiking trail, Well, That Was Awkward is serving up the ultimate playlist of star-studded slip-ups, blunders, and “did that just happen?” moments. Bree and Mendy swap their own cringe-meets-comedy celebrity encounters—like the time Bree sat between her husband and the last man left on her Hall Pass list (sorry, Spalding Gray), and when Tony Danza spent an entire three-act Eugene O’Neill drama...
19
Oct. 24, 2024

Only Neighbors – Too Close for Comfort

Welcome to another awkward-filled episode of Well, That Was Awkward with Bree and Mendy! In this intimate installment, Bree and Mendy dive into the theme of awkward neighbor stories. They share their own personal experiences, from sneaky pets to avoiding neighbors while stoned, and even discuss a listener's tale of an unexpected sight during a late-night baseball game. Along the way, they embrace the joy of awkwardness and remind us all that sometimes, the best thing to do is laugh through it. ...
14
Aug. 29, 2024

Butterfingers and the Bomb: An Unexpected Journey from Draft to Laughs

In this episode of Well, That Was Awkward, Bree and Mendy share an incredible story from one of their listeners, Paul, whose journey from a law school student to a soldier during the Vietnam War takes a surprisingly hilarious and awkward turn. Get ready to hear about Paul's unique draft experience, his run-ins with bullies during basic training, and an unexpected assignment with nuclear weapons! Mendy kicks off the episode with a story about her crush on Noam Chomsky and a memorable encounter...
13
Aug. 22, 2024

Sebastian the Superhero: When A Good Deed Goes Wrong

Welcome to another episode of "Well That Was Awkward," where we dive into the hilariously cringeworthy and downright awkward moments that life throws our way. In this episode, Bree and Mendy are back with stories that will make you laugh, cringe, and maybe even rethink your next good deed!