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.

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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:

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.

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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:

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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.

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

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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:

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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.

💌 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.

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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:

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 

[email protected]

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.

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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:

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!

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You’re out of lockdown, finally at a real wedding again, and someone on the dance floor catches your eye. There’s chemistry, connection, shared moon signs, and just the right amount of glitter. But sometimes, even when the vibes are right, the love connection takes an unexpected turn.

In this episode of Well, That Was Awkward, Mendy and Bree share a listener story full of post-pandemic hope, woo-tinged romance, Nashville nightlife, and one of the most awkward twists we’ve heard in a while. From wedding dance floors to burlesque bars to velvet couches, this one has it all.

As always, we’ll celebrate the awkward, embrace the unexpected, and ask ourselves the most important question: What would Dana do?

In This Episode:

Listener Advisory:

Contains adult themes, queer dating mishaps, mild swearing, and irreverent woo.

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In this solo episode of Well, That Was Awkward, Mendy takes the mic alone – But things escalate quickly when Mendy recounts a surprisingly flirty run-in with a car detailer named Lucky, who offers more than just a clean ride.

What starts as a simple oil change turns into a rhyming text exchange, a dirty Lexus, and a minor emotional entanglement. Mendy shares the play-by-play of how she accidentally had an affair… From clever rhymes to uncomfortable realizations, this is a hilarious and painfully relatable tale about boundaries, intentions, and how quickly friendliness can get misread.

In This Episode:

Call to Action:

Ever had a “wait, was that flirting?” moment? Or a flirty moment you really didn’t ask for?

Share your story with us! Use the submission link in the show notes or head to https://www.awkwardsagemedia.com/show/well-that-was-awkward-podcast/ You might hear it on a future episode!

Credits:

Host + Writer: Mendy St. Ours

Producer + Editor: Bree Luck

A production of Awkward Sage Media

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