Comedy Episodes

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...

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 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 stra...

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 painfu...

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., betrayal, and one very loud Dodge Charger. It’s a tale of forbidden pop culture, nosy neighbors, t...

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-shaped gift box: Sammy’s awkward Christmas saga: A family gathering that makes even the worst Se...

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 really bad round of Jeopardy, this episode is packed with fun, friendship, and 80s flashbacks. Ce...

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 the joy of awkwardness and remind us all that sometimes, the best thing to do is laugh through it. ...

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 personal issue, Margaret faces an awkward moment that could have jeopardized her professional reputation....

Ever 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 superpow...

In 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 ...

This 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...

This 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?

Welcome 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 Misplace...

Welcome 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-teache...

Welcome 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! Takeawa...

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...