Well, That Was Awkward

Awkward stories, big laughs, (pretty much)zero judgment. Join Mendy and Bree, your utterly unqualified awkwardness experts, as they unpack hilarious, cringeworthy moments from people like you. Get ready to say ”Oh noooo!” out loud, then secretly feel better about your own life.

Well, That Was Awkward is a comedy podcast hosted by wellthatwasawkward, with 37 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

wellthatwasawkward hosts Well, That Was Awkward, a comedy show with 37 episodes published.

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  Episode #34

  The Truth About Why French Canada Got Super Awkward

  Aug 28, 202513 minS0

  <p>Grab your flannel shirts and Sun-In, because Mendy is taking us back to the summer of 1994 —where lifeguard shifts, band camp, and a French class trip turned into something unforgettable.</p> <p>From roller skating to French disco to swooning over a dreamy Canadian tour guide, it was the kind of teenage adventure that felt like pure magic… until a late-night prank at the hotel tipped everything straight into awkward chaos.</p> <p>What happened next left a busload of teenagers horrified, a tour guide disappointed, and Mendy mortified enough to cry all the way home.</p> <p>This epis...

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  Episode #33

  100% Chance of Awkwardness: From Childhood Fame to Small-Town Shame

  Aug 21, 202527 minS0

  <p>In this episode of Well, That Was Awkward, Mendy and Bree bask in the hilarity of the awkward, celebrating the moments that leave us red-faced but connected. Fresh off their Best of C-Ville award win (and plotting the deviled egg party spread), they invite listeners to join their Facebook group and send in stories that prove awkwardness is universal.</p> <p>This week’s story spotlights Stephanie (aka Jen), a former child star of community theater with equal parts talent and ambition — and a knack for unforgettable mishaps. From starring in jazz cantatas about biblical floods to an infamous rest...

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  Episode #32

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

  Aug 14, 202536 minS0

  <p>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.</p> <p>Our listeners don’t hold back either: nearly bumping Jennifer Aniston off a sidewalk cur...

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  Episode #31

  When Your Side Hustle Serves You Humble Pie

  Aug 7, 202510 minS0

  <p >Bree here. It’s 4 AM. I’ve got flour in my hair, burns on my arms, and questions about my life choices.</p> <p >In this solo installment of Awkward and Alone, I share what happened when I—middle-aged arts executive, story-slinger, and resident night owl—decided to take a second job… at a bakery. Why? Because I wanted something “real.” (Spoiler: it got real fast.)</p> <p >This is a tale of romanticized routines, edible glitter fantasies, and being publicly outed for doing honest work. It’s also about ego, identity, and remembering that hard, awkward, physical labor can be both ego...

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  Episode #30

  When it Comes to LOVE, Three is the Awkward Number… Or Is It?

  Jul 31, 202526 minS0

  <p>A dead butterfly wedding tribute.</p> <p>A throuple in a walk-in closet.</p> <p>An ex at the door.</p> <p>This week, we hear from a listener whose spring break turned into a science-backed, champagne-fueled throuple… until his ex crashed the party.</p> <p>Also:</p> <p>🦋 The world’s most tragic butterfly release</p> <p>📚 Sex ed memories involving cartoon nudity and romance novels</p> <p>💬 Advice from a former wallflower turned botanical Casanova</p> <p>Don’t open the door. Don’t shake the box. And whatever you do, don’t miss this episode.</p> <p>🤓Referenced in th...

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