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
Claim This Podcastby wellthatwasawkward
5.0(28 reviews)
37 episodes
Updated Bi-weekly
Accepts GuestsHas SponsorsLocation 🇨🇦
70
Podcast Authority
BetaGoodBased on show quality, social media presence, reviews, charts, and more
Quality56
Social94
YouTube93
Engagement71
Podcast Overview
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.
Language
🇺🇲
Publishing Since
4/16/2024
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70
Podcast Authority
BetaGoodBased on show quality, social media presence, reviews, charts, and more
Quality56
Social94
YouTube93
Engagement71
7
Excellent Areas
2
Good Performance
10
Growth Opportunities
excellent
Episode Length
22 minutes
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good
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Every 13 days
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Recent Episodes
August 28, 2025
The Truth About Why French Canada Got Super Awkward
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. 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. What happened next left a busload of teenagers horrified, a tour guide disappointed, and Mendy mortified enough to cry all the way home. This episode has it all: ’90s nostalgia, travel mishaps, high school crushes, and the kind of teenage mischief that only makes sense decades later when you can finally laugh about it. 🎧 Listen now to relive the awkward glory of the Summer of ’94. 🔗 Connect with us: Share your own awkward story (Anonymously or not!) via the WTWA Form Leave us a voice memo on the WTWA Website Follow us on Instagram: @awkwardsagemedia Send us an email: wellthatwasawkwardpodcast@gmail.com Support the show at Buy Me A Coffee Save 10% on your Monk Manual at monkmanual.com/AWKWARD using code AWKWARD Don’t forget to follow the show wherever you listen!
August 21, 2025
100% Chance of Awkwardness: From Childhood Fame to Small-Town Shame
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. 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 restaurant “incident,” her story reminds us that the things we once thought might ruin us often become our best material. With nostalgia, 80s flair, and their signature irreverence, Bree and Mendy spin Stephanie’s childhood embarrassments into pure comedy gold. Along the way, they remind us that awkwardness isn’t a flaw — it’s a feature. What You’ll Hear in This Episode: WTWA’s Best of C-Ville award win and what it means How awkwardness connects us (and why we love it) Listener story: from child star to small-town embarrassment Church musicals, theater moms, and jazz cantatas about floods The infamous “pizzeria moment” (aka awkward glory at its finest) Why awkward childhoods often make the most creative adults Here’s Jen’s Website, as promised: https://jenniferhoyttidwell.com/ Join the Awkward Community: 👉 Share your story or send us a message in the WTWA Facebook Group 👉 Keep awkward alive — subscribe, rate, and review Well, That Was Awkward wherever you listen to podcasts. 🔗 Connect with us: Share your own awkward story (Anonymously or not!) via the WTWA Form Leave us a voice memo on the WTWA Website Follow us on Instagram: @awkwardsagemedia Send us an email: wellthatwasawkwardpodcast@gmail.com Support the show at Buy Me A Coffee Save 10% on your Monk Manual at monkmanual.com/AWKWARD using code AWKWARD Don’t forget to follow the show wherever you listen!
August 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 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 🔗 Connect with us: Share your own awkward story (Anonymously or not!) via the WTWA Form Leave us a voice memo on the WTWA Website Follow us on Instagram: @awkwardsagemedia Send us an email: wellthatwasawkwardpodcast@gmail.com Support the show at Buy Me A Coffee Save 10% on your Monk Manual at monkmanual.com/AWKWARD using code AWKWARD Don’t forget to follow the show wherever you listen!
37 total episodes available
Recent guests on Well, That Was Awkward
Guests from recent episodes — sign up to see every guest that has ever appeared on this show.
Mendy St Ours
Guest
Denise Stewart
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Melody
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Frequently asked questions
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- What is Well, That Was Awkward?
- How often does this podcast release new episodes?
This podcast updates bi-weekly.
- Where can I listen to this podcast?
This podcast is available on 9 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
- Does this podcast accept guests?
Yes, this podcast regularly features guests.
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