Well, That Was Awkward

wellthatwasawkward
  • 5.0 (14)
  • COMEDY
  • UPDATED WEEKLY

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.

  1. The Truth About Why French Canada Got Super Awkward

    08/28/2025

    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!

    13 min
  2. 100% Chance of Awkwardness: From Childhood Fame to Small-Town Shame

    08/21/2025

    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!

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

    08/14/2025

    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!

    36 min
  4. When Your Side Hustle Serves You Humble Pie

    08/07/2025

    When Your Side Hustle Serves You Humble Pie

    Bree here. It’s 4 AM. I’ve got flour in my hair, burns on my arms, and questions about my life choices. 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.) 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-bruising and soul-soothing. Tune in for laughs, burns (literal and emotional), and a reminder that even when we’re flailing—we’re never really alone. Things You’ll Hear in This Episode: Bree’s dreamy fantasy of bakery life… and the gritty, flour-covered truth That time someone shouted across a room about her new job What it means to be terrible at something (and keep doing it anyway) Why non-slip Swedish clogs are a LIE The unexpected joy of manual labor… and heating pads 🔗 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!

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

    07/31/2025

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

    A dead butterfly wedding tribute. A throuple in a walk-in closet. An ex at the door. This week, we hear from a listener whose spring break turned into a science-backed, champagne-fueled throuple… until his ex crashed the party. Also: 🦋 The world’s most tragic butterfly release 📚 Sex ed memories involving cartoon nudity and romance novels 💬 Advice from a former wallflower turned botanical Casanova Don’t open the door. Don’t shake the box. And whatever you do, don’t miss this episode. 🤓Referenced in this episode: Where Did I Come From? by Peter Mayle — A beloved illustrated children’s guide to the facts of life, in print since 1973 with over 1 million copies sold. It’s lighthearted, honest, and touches on everything from anatomy to conception in a way young readers can understand  . You can grab it from major retailers like Barnes & Noble or Amazon. For instance: Barnes & Noble: Where Did I Come From? 50th Anniversary Edition: An Illustrated Children’s Book on Human Sexuality by Peter Mayle (ISBN: 9780806542287) Also available under variations like the 1973 original or other paperback editions (ISBN: 0818402539 / 9780818402531) 🔗 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!

    26 min
  6. She Found Her Stolen Car… With a Psychic Hunch and a Booby Trap

    07/24/2025

    She Found Her Stolen Car… With a Psychic Hunch and a Booby Trap

    Mendy’s riding solo—and taking you on a truly absurd (but 100% real) journey through amateur detective work, neighborhood drama, and a very misunderstood pair of underwear. Also featured? A severed hand, a fake penis, and one heroic fishing vest rescue. Solving crime is awkward, y’all! If you’ve ever felt like a badass and then watched your dignity slide down a storm drain—this one’s for you. 💅 What’s Inside This Mess: Why Mendy got certified as a PI (but never went full Veronica Mars) Finding a stolen car… twice True crime podcasts vs. real-life Facebook sleuthing The “Car Penis”: its origin story and unfortunate police discovery A heartfelt tribute to her neighborhood watch crew (feat. Jodi from Louisiana) The case of the brown-stained undies and the crumbling illusion of cool 💌 Call to Action: Have you ever tried to impress someone… only to end up confessing ownership of something deeply regrettable in front of the police? We need your story. Send it in and maybe you’ll get to awkward-brag on the next episode. 🔗 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!

    18 min
  7. Bear With Us — These Might Be the Worst Camping Decisions Ever

    07/17/2025

    Bear With Us — These Might Be the Worst Camping Decisions Ever

    What do you do when someone asks you to do something you absolutely do not want to do, but they think they’re offering you an honor? This week, Bree and Mendy tackle the awkwardness of saying no when saying yes feels like a social trap. And speaking of traps, they also share a listener story that includes hiking, exotic dancers, two dudes marinated in fish slime, and one “bear” attack in the Wyoming wilderness. It’s equal parts adventure, absurdity, and advice on what not to do in grizzly country. In This Episode: Bree and Mendy on awkward invitations and how to decline without spiraling into guilt Bree’s go-to “I don’t have the bandwidth” line (feel free to steal it) Mendy’s clever tactics to ghost unwanted social obligations Listener story: A 1985 misadventure involving two friends, some fishy decisions, and a misunderstood tree limb A bear scare that turns out to be snoring + nature = comic gold What not to pack in your tent (hint: it’s trout) Why you should never hike in bear country with nothing but colored pencils How Dana (imaginary bestie and part-time exotic dancer) would have handled it differently Our Favorite Takeaway? If you’re going to cook dinner in the woods, maybe don’t turn your tent into a trout-scented snack pack. Listener Story Credit: Thanks to “Andrew” (and “Gary”) for sharing your hilarious and oddly inspiring tale of wilderness survival, near-bear encounters, and post-strip-club camping. Want to share your awkward story? We love hearing from you. Email us your most awkward encounter at  wellthatwasawkwardpodcast@gmail.com CTA: If you laughed, cried, or opened a tin of sardines after listening to this episode, leave us a review, share the episode with your weirdest friend, and remember: you may be awkward, but you’re definitely not alone. 🔗 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!

    23 min
  8. I Got Married at 22 and Invited My Ex -- Here's the Awkward Truth

    07/10/2025

    I Got Married at 22 and Invited My Ex -- Here's the Awkward Truth

    In this solo episode, Bree dishes from a literal closet at her mother-in-law’s Cape Cod home about her awkward journey into marriage at age 22. From engagement party antics at the Plaza Hotel to wedding-day wardrobe disasters involving high heels in soft grass, Bree humorously explores the messy decisions of young adulthood. Highlighted by an ex-boyfriend who made a bizarre fashion choice when he decided to attend her union, Bree's wedding story proves that awkwardness is both universal and strangely endearing. Tune in for laughs, relatable moments, and reassurance that no matter how awkward things get, you're never alone. In This Episode: Bree's existential closet musings: Why is her wedding photo tucked away next to old shoes? Why getting married at 22 might not have been her brightest decision, but, hey, it took! Bree’s swanky (but actually super sketchy) engagement party at the Plaza Hotel. The legendary appearance of Nikolai, the ex who crashed Bree’s ceremony in a clown nose. The epic "Linebacker-Hemingway Minister vs. Party Clown Ex" showdown at the after-party. The awkward and ultimately sweet moments that defined Bree's uniquely chaotic wedding. Call to Action: Awkward wedding tales unite us all—what's yours? Send your wonderfully weird stories our way, and you just might hear them featured in a future episode! 🔗 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!

    20 min
See All (37)

Trailer

5
out of 5
14 Ratings

About

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.

Information

  • Creator
    wellthatwasawkward
  • Years Active
    2024 - 2025
  • Episodes
    37
  • Rating
    Explicit
  • Copyright
    © Copyright 2024 All rights reserved.
  • Show Website
    Well, That Was Awkward