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 winking at Mendy.

Our listeners don’t hold back either: nearly bumping Jennifer Aniston off a sidewalk curb, falling into Christopher Reeve’s arms on the subway, mistaking Bruce Springsteen for just another guy hogging a pool lounger, and getting a 3 AM call meant for the Steven Tyler from Aerosmith. You’ll also hear tales of running into Glenn Close while wearing questionable maternity wear, and exactly what celebrities really smell like.

Packed with celebrity names, awkward charm, and “you can’t make this stuff up” storytelling, this episode is a must-listen for pop culture junkies, nostalgia lovers, and anyone who’s ever accidentally made a fool of themselves in front of a famous person.

Episode Highlights:

• The cowboy boot obsession that led Bree straight to Brad Pitt in Santa Fe
• Mendy’s theory on why you should pretend you don’t recognize famous people
• A Runyon Canyon run-in with Jennifer Aniston (and her playful side)
• Morning sickness meets Glenn Close on a New York sidewalk
• Falling—literally—into Superman’s arms
• How to accidentally diss Bruce Springsteen poolside
• The Steven Tyler mix-up that almost got champagne and “ladies” delivered to the wrong guy
• Bree’s Hall Pass dilemma in a movie theater
• Mendy’s summer of 1999 Tony Danza flirt-fest during The Iceman Cometh

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