Well, That Was 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...

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...

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...

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, e...

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 Casano...

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. 💅 W...

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 Wyomi...

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...

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-t...

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 accidentall...

In this season premiere of Well That Was Awkward, Bree and Mendy crack open the vault of 1991 with a scandal so juicy it practically rewinds itself. Our heroine, Dee Dee (a.k.a. the ever-iconic Denise Stewart), finds herself in the middle of a VHS-fueled covert mission to record Madonna’s Blonde Ambition Tour… without her best friend’s military mom finding out. What follows is a story of S.E.X., b...

Season 1 is in the books, folks! In this finale episode, Mendy and Bree spill the tea on the joy (and sheer awkwardness) of connecting with you, our lovely listeners. Plus, Bree confesses her hairdresser dilemma, Mendy recounts an awkward moment involving their podcast’s title, and the duo invites YOU to share your awkward stories for Season 2. What’s Inside This Episode: Mendy’s awkward encounter...

Holidays bring family, food, and a whole lot of awkwardness. Bree and Mendy share one of the most hilariously bizarre listener-submitted stories this week. Our listener, Melody, finds that  Christmas morning takes an unexpected turn when Grandma doesn’t show up to the festivities, leaving the family to juggle big feelings, a breakfast casserole, and Uncle Steve’s Hell’s Angels hangover. From diape...

Get ready to up your awkward game this holiday season! In this surprise minisode, Bree and Mendy announce something exciting: Well, That Was Awkward, The Party Game! This free storytelling game lets you share your funniest, most cringe-worthy, and awkward moments with family, friends, or coworkers. Tune in to find out how you can download the game, what you’ll need to play, and why this is the per...

Ah, the holidays. A time for twinkling lights, festive cheer, and… family-induced trauma disguised as a gift exchange. In this episode, Bree and Mendy unwrap (see what we did there?) Sammy’s jaw-dropping story of holiday hierarchy. Imagine getting tumblers while your stepsiblings are handed Cartier watches and kid-sized Land Rovers. Yeah, that kind of holiday.  Here’s what’s inside this episode-sh...

This week, Bree and Mendy share a listener’s unforgettable story of teenage love, heartbreak, and one hilariously awkward date in Brooklyn. From a kiss that could rival a rom-com to a Venmo request that shattered the illusion, this episode is packed with laughs, tears, and relatable moments. In addition, Bree and Mendy share their own awkward tales of broken laptops, nerd dates, and revisiting boo...

Join Bree and Mendy as they share memories of 80s nostalgia, awkward breakups, and musical mishaps! This episode features Darla’s story of romantic despair—complete with botched song lyrics and a surprise roadside breakup! Bree and Mendy explore the awkward side of 80s fashion, misheard lyrics, and cringe-worthy moments we’d rather forget (or sing about). Whether it’s high hair, leg warmers, or a...

Welcome to another awkward-filled episode of Well, That Was Awkward with Bree and Mendy! In this intimate installment, Bree and Mendy dive into the theme of awkward neighbor stories. They share their own personal experiences, from sneaky pets to avoiding neighbors while stoned, and even discuss a listener's tale of an unexpected sight during a late-night baseball game. Along the way, they embrace...

In this episode, Bree and Mendy share the mic with the real-life Dana, whose wisdom and hilarity take center stage. Together, they unpack listener stories, including Denise’s poetic third-grade hustle, Dr. Greg's unforgettable gaseous mishap, and an anonymous caller’s crockpot weed discovery. Plus, they welcome a special WEDDING story from Shaneisha Wofford. Oh, and  Bree gets mooned by a familiar...

In this episode of Well That Was Awkward, Bree and Mendy dive deep into the world of awkwardness and human connection with their first-ever guest, Dr. Jim Coan, professor of psychology and head of the Virginia Affective Neuroscience Lab. Together, they explore the science behind why awkward moments can actually bring us closer, how discomfort creates bonds, and why a cringe-worthy encounter could...

In this hilariously awkward episode, Bree and Mendy dive into the story of Matthew, whose European adventures take a turn for the awkward when he finds himself navigating a boomerang relationship. From navigating the tricky dynamics of an on-again, off-again relationship to getting stood up at just the wrong time, this story hits all the right notes of cringe, humor, and surprise. Key highlights i...

We’ve got some news, folks! Bree and Mendy are taking a little breather… sort of. While we’re still here for all your awkward needs, we’re mixing things up a bit and going bi-weekly. That’s right, we’ll be dropping new episodes every other week.  📅 What’s New? Episode Drops Every Other Week: You can still get your awkward fix, just with a little more anticipation built in! YouTube Goodness: We’re...

In this episode of Well, That Was Awkward, Bree and Mendy share an incredible story from one of their listeners, Paul, whose journey from a law school student to a soldier during the Vietnam War takes a surprisingly hilarious and awkward turn. Get ready to hear about Paul's unique draft experience, his run-ins with bullies during basic training, and an unexpected assignment with nuclear weapons! M...

Welcome to another episode of "Well That Was Awkward," where we dive into the hilariously cringeworthy and downright awkward moments that life throws our way. In this episode, Bree and Mendy are back with stories that will make you laugh, cringe, and maybe even rethink your next good deed! In This Episode: First In-Person Recording: Bree and Mendy share the excitement (and awkwardness) of recordin...

In this episode, Bree and Mendy unravel the hilariously awkward story of Margaret, a high-flying business consultant who unknowingly lets her love for garlic almost derail her career. From her early days as a competitive child to landing prestigious positions at top consulting firms, Margaret's journey is nothing short of remarkable. But when a well-meaning family intervention reveals a very perso...