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Wellthatwasawkward

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Well, That Was Awkward
Well, That Was AwkwardThe Truth About Why French Canada Got Super AwkwardGrab 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 epis...
2025-08-2812 minWell, That Was Awkward
Well, That Was Awkward100% Chance of Awkwardness: From Childhood Fame to Small-Town ShameIn 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 rest...
2025-08-2126 minWell, That Was Awkward
Well, That Was AwkwardBrad Pitt, Glenn Close, and Tony Danza Walk Into a Podcast: Our Most Awkward Celebrity MomentsFrom 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 cur...
2025-08-1436 minWell, That Was Awkward
Well, That Was AwkwardWhen Your Side Hustle Serves You Humble PieBree 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...
2025-08-0710 minWell, That Was Awkward
Well, That Was AwkwardWhen 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 th...
2025-07-3125 minWell, That Was Awkward
Well, That Was AwkwardShe Found Her Stolen Car… With a Psychic Hunch and a Booby TrapMendy’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...
2025-07-2417 minWell, That Was Awkward
Well, That Was AwkwardBear With Us — These Might Be the Worst Camping Decisions EverWhat 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...
2025-07-1722 minWell, That Was Awkward
Well, That Was AwkwardI Got Married at 22 and Invited My Ex -- Here's the Awkward TruthIn 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....
2025-07-1019 minWell, That Was Awkward
Well, That Was AwkwardWhy You Should Never Date During Mercury RetrogradeYou’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...
2025-07-0322 minWell, That Was Awkward
Well, That Was AwkwardAwkward Confession: The Accidental AffairIn 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 T...
2025-06-2609 minWell, That Was Awkward
Well, That Was AwkwardThe Madonna Tape Heist: Scandals and Small Town Secrets RevealedIn 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., betrayal, and one very loud Dodge Charger. It’s a tale of forbidden pop culture, nosy neighbors, teenage code-breaking, and the long road back into a small...
2025-06-1931 minWell, That Was Awkward
Well, That Was AwkwardHow to Cheat on Your Hairdresser (and Handle Awkward Encounters Like a Pro)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 explaining the podcast title to an old friend. Bree’s confession about cheating on her beloved hairdresser. A thank-you to all our listeners who shared and resonated with our awkward stories...
2025-01-0209 minWell, That Was Awkward
Well, That Was AwkwardGrandma Got Run Over By A Casserole: Awkward Christmas StoriesHolidays 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 diaper rash cream miscommunications to Bree’s “glasses invisibility” dilemma, the hosts dive headfirst into the beauty of embracing life’s absurd moments. Plus, they reflect on the intersection of grief, awkwardness, and humanity in this touchin...
2024-12-1931 minWell, That Was Awkward
Well, That Was AwkwardBONUS: Well, That Was Awkward: The Game You Didn’t Know You NeededGet 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 perfect icebreaker for holiday gatherings. Plus, hear some hilarious examples of how you can embrace the awkward and make unforgettable memories.   Download the Game: Click the...
2024-12-1202 minWell, That Was Awkward
Well, That Was AwkwardA Very Awkward Holiday: When Gifting Goes WrongAh, 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-shaped gift box: Sammy’s awkward Christmas saga: A family gathering that makes even the worst Secret Santa feel like a dream. The art of passive-aggressive revenge: From strategic gift-giving to killer game night comebacks...
2024-12-0539 minWell, That Was Awkward
Well, That Was AwkwardHeartbreak on the L Train: When Love Goes from Dreamy to DisastrousThis 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 books they forgot they’d already read. Whether it’s reliving high school heartbreaks or celebrating the awkwardness of daily life, this episode reminds us that you may be awkward, but you're defini...
2024-11-2139 minWell, That Was Awkward
Well, That Was AwkwardFrom Big Hair to Breakups: The Ultimate 80s Awkward StoryJoin 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 really bad round of Jeopardy, this episode is packed with fun, friendship, and 80s flashbacks. Celebrity Shoutouts: Frisco & Felicia (General Hospital), Bo and Luke Duke (The Dukes of Hazzard), Ricky Schroder...
2024-11-0731 minWell, That Was Awkward
Well, That Was AwkwardOnly Neighbors – Too Close for ComfortWelcome 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 the joy of awkwardness and remind us all that sometimes, the best thing to do is laugh through it. You'll hear stories about: Bree’s giant dog Basho, who mastered an impressive disappearing ac...
2024-10-2437 minWell, That Was Awkward
Well, That Was AwkwardVacation Mode: Corrupting Canadians, Crockpot Weed, Zoom Moonings and More!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 fanny during a Zoom call... Can you guess who it is? Thank yous: A huge thank you to our surprise guest Dana for joining us -- and to all the callers—Denise, Dr. Greg, Shaneis...
2024-10-1034 minWell, That Was Awkward
Well, That Was AwkwardWe Made It Awkward With An Expert: Dr. Jim CoanIn 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 be the best thing to happen in a relationship. Dr. Coan shares personal stories of awkward moments, from a mistaken kiss in the car to navigating uncomfortable conversations around sex, revealing how these moments...
2024-09-2640 minWell, That Was Awkward
Well, That Was AwkwardStranded in Spain: When Love Goes Off the RailsIn 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 include: The unique dynamics of boomerang romances and how Matthew found himself in a series of geographical "on-again, off-again" relationships. The awkwardness of being stranded in a foreign country with no money...
2024-09-1235 minWell, That Was Awkward
Well, That Was AwkwardWhy We're Hitting Pause on Weekly Episodes (Spoiler: It’s Awkward)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 not leaving you hanging! Between episodes, catch us on YouTube for exclusive video clips. Make sure to subscribe so you don’t miss out! Stay Conne...
2024-09-0502 minWell, That Was Awkward
Well, That Was AwkwardButterfingers and the Bomb: An Unexpected Journey from Draft to LaughsIn 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! Mendy kicks off the episode with a story about her crush on Noam Chomsky and a memorable encounter at MIT, setting the stage for a discussion on parasocial relationships with celebrities. Bree...
2024-08-2929 minWell, That Was Awkward
Well, That Was AwkwardSebastian the Superhero: When A Good Deed Goes WrongWelcome 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 recording in person for the first time, complete with multi-camera action and all the self-soothing habits they have to leave behind. From picking noses to dealing with the new "hot pink beeper," the transition...
2024-08-2233 minWell, That Was Awkward
Well, That Was AwkwardWhat Happens When One Woman's High Stakes Life Kinda StinksIn 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 personal issue, Margaret faces an awkward moment that could have jeopardized her professional reputation. Through laughter and reflection, Bree and Mendy discuss the impact of personal quirks on professional life, the importance of self-awareness, and how even...
2024-08-1531 minWell, That Was Awkward
Well, That Was AwkwardFrom Faux Pas to Fabulous How One Girl Owned Her Unique StyleEver felt that cringe-worthy moment when you wish you could take back something you said or did? Join Mendy and Bree as they celebrate the awkward moments we all experience. This week, we hear a story about our worst middle school nightmare -- getting laughed at by a room full of mean girls! Plus our hosts divulge their own awkward stories from the week.  Protective Awkwardness Mendy shares a story about defending her partner at the pool, showcasing how our awkwardness can become a superpower when protecting loved ones. We explore why we're often more assertive in d...
2024-08-0830 minWell, That Was Awkward
Well, That Was AwkwardThe Super Awkward Elevator Episode: How to survive when you're stuckIn this episode, Bree and Mendy explore the hilariously awkward and slightly terrifying experience of Ellie, who got stuck in an elevator just before Christmas. They discuss strategies for handling awkward moments, particularly in confined spaces, and share their own cringeworthy encounters. Ellie’s story is a rollercoaster of emotions, complete with lo mein noodles, lipstick messages, and a heroic rescue by her best friend. The episode wraps up with a special message from Synthia Scott Kearney – and offers a valuable tip for anyone who might find themselves stuck in an elevator. (Thank you, Synthia!) Bullet Points: A...
2024-08-0125 minWell, That Was Awkward
Well, That Was AwkwardHot Hippie Summer: The Greatest Awkward Breakup Story Ever ToldThis week, Mendy and Bree talk about strategies for dealing with restroom knockers and come up with a business plan for making your next trip to the loo a little less awkward. The episode's highlight is a listener story from Lane. We hear all about how her summer romance with Tristan, a high school acquaintance turned love, blossoms over shared values.  But will their summer romance wilt on the vine? The episode ends on a hopeful note, encouraging listeners to embrace awkwardness and life's lessons.   Bullet Points   - The theme of awk...
2024-07-2528 minWell, That Was Awkward
Well, That Was AwkwardHigher Math: This is your brain on CalculusThis week, Bree and Mendy dive into a listener's hilariously awkward high school story that involves perms, weed, and a surprising triumph in a calculus class. Plus, they share their own awkward moments and serenade you with a special song at the end. Don’t miss out on this 80s flashback that will have you laughing out loud and reminiscing about your own high school days. Key Themes: Summertime awkward moments (FREE THE NIPS… maybe?) High school memories  Awkward fashion and hairstyles of the 80s The adventures (and misadventures) of smoking weed in high school Unexpected acade...
2024-07-1821 minWell, That Was Awkward
Well, That Was AwkwardSavannah Surprise: What happens when a date gets really awkwardThis week, Bree and Mendy dive into the cringe-worthy adventures of George Steele. Join us as we unravel George's impulsive trip to Savannah with a dating app match? Will they find a love connection in the land of Southern charm – or will the whole relationship go up in flames? Key Themes: Embracing awkward moments The ups and downs of dating Savannah travel highlights and mishaps Awkward Stories of the Week: Mendy’s Awkward IUD Change: A medical procedure turned into a musical moment. Bree’s Group Chat Mishap: But if you want to buy us a c...
2024-07-1134 minWell, That Was Awkward
Well, That Was AwkwardThe Fireworks Episode: A Sure Fire Way to Laugh TodayWelcome to a special holiday episode of "Well, That Was Awkward," where Bree and Mendy share the most hilariously cringeworthy voicemails submitted by our beloved listeners. Celebrating Independence Day with a bang, we’ve got tales of embarrassing encounters, unexpected discoveries, and awkward celebrity run-ins. Key Themes: We REALLY REALLY Want to hear from you! Share your story with us! Embarrassing encounters at public places Celebrity sightings and awkward interactions Misplaced items leading to awkward situations Hilarious misunderstandings and social faux pas Listener Stories: Bagel Shop Blunder: A listener recounts a mortifying moment at Bo...
2024-07-0428 minWell, That Was Awkward
Well, That Was AwkwardAwkward Zoom Moments: A Parent-Teacher Conference DisasterWelcome to another episode of "Well, That Was Awkward," where Bree and Mendy dissect listener's most cringe-worthy and hilarious moments with warmth, wit, and irreverent insight. In this episode, join us as we explore the world of Zoom fails, unexpected emotional moments, and the importance of humor in navigating awkward situations. Key Themes: The emotional rollercoaster of losing a beloved pet The hilariously awkward consequences of an unexpected Zoom fail Navigating parent-teacher conferences during a pandemic The resilience and humor required to handle public embarrassment Creative problem-solving in the face of virtual communication mishaps Takeaways:
2024-06-2730 minWell, That Was Awkward
Well, That Was AwkwardCheeky Charlotte: Mischief And Mayhem That Will Make You LaughWelcome to Episode 4 of "Well, That Was Awkward," where Bree and Mendy share and dissect our listeners' most cringe-worthy and hilarious moments. Join us as we delve into the world of childhood mischief, grown-up pranks, and the lasting power of humor. Key Themes: Mischievous childhood antics and their lasting impacts Resilience and humor in navigating public embarrassment The joy of connecting through shared awkward moments The importance of looking before you smack! Takeaways: Embrace the unexpected with humor and grace. Use awkward moments as opportunities to bond and empathize with others. Always make sure...
2024-06-2029 minWell, That Was Awkward
Well, That Was AwkwardFrom Fart to Finish: The Funniest Theater BlundersWelcome to another episode of "Well, That Was Awkward," where Bree and Mendy share and dissect life's most cringe-worthy and hilarious moments with warmth, wit, and irreverent insight. In this episode, join us as we explore the world of theater blunders, unexpected bodily functions, and the power of humor in the face of embarrassment. Key Themes: Theater mishaps and live performance challenges The awkwardness of unexpected bodily functions The resilience and humor required to navigate public embarrassment The importance of shared experiences and empathy in awkward situations Creative problem-solving in the face of embarrassment Takeaways: Embrace the unexpected...
2024-06-1334 minWell, That Was Awkward
Well, That Was AwkwardMuscle Maniac Meltdown: Let's Get Physically Awkward!Welcome to "Well, That Was Awkward," where hosts Bree and Mendy share stories of life's most cringe-worthy moments with humor, warmth, and irreverent insight. In this episode, join us as we unpack Ben's hilariously mortifying encounter at the gym and explore the hilarious aftermath of an unplanned fitness disaster.  Key Themes: A listener story that will make you queasy. The pitfalls of trying too hard to impress at the gym. The delicate balance of social dynamics around hookups. Embracing awkward moments with humor and grace. Tips on how to avoid gym-related embarrassments. Takeaways: Don't o...
2024-06-0636 minWell, That Was Awkward
Well, That Was AwkwardGood Vibrations: An Awkward Tale of Moving Mishaps and Surprise VisitsWelcome to "Well, That Was Awkward," where hosts Bree and Mendy share stories of life's most cringe-worthy moments with humor, warmth, and irreverent insight. In this episode, join us as we unpack Taylor's jaw-dropping encounter with Meadowhaven management and explore the hilarious aftermath of an unplanned inspection... Key Themes: A listener story leaves us vibing. Creative problem-solving in awkward situations. Embracing empowerment and owning quirks with humor. Strategies for navigating shame and embarrassment with wit and whimsy. The liberating power of outrageous solutions in embarrassing predicaments. Takeaways: Embrace embarrassment with humor, creativity, and self-assurance. ...
2024-05-3034 minWell, That Was Awkward
Well, That Was AwkwardWell, That Was Awkward- The Trailer!Join Mendy St. Ours and Bree Luck, your unqualified, yet certified awkwardness experts as they launch a podcast dedicated to exploring (and celebrating) the hilariously uncomfortable moments we've all experienced.   This trailer is a sneak peek at what awaits you: listener-submitted stories, side-splitting commentary, and a supportive space to celebrate (and dissect) the awkwardness that unites us.   ***NEW EPISODES DROP IN MAY!*** In This Trailer, You'll Hear: Our catchy new theme song tune, written by Mendy. A glimpse into the relatable awkward situations we all face The promise of...
2024-04-1701 min