Videos

Dec. 19, 2024

Grandma Got Run Over By A Casserole: Awkward Christmas Stories

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,…

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Dec. 12, 2024

BONUS: Well, That Was Awkward: The Game You Didn’t Know You Needed

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…

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Dec. 6, 2024

🎉 Make Your Holidays Awkward (On Purpose!) 🎉

🎉 Make Your Holidays Awkward (On Purpose!) 🎉 We turned our podcast, Well, That Was Awkward, into the ultimate party game—and it’s FREE! If you love laughing at life’s weirdest, funniest moments (and sharing your own), you need to try Well, That Was Awkward: The Party Game. ✔️ Perfect for…

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Dec. 5, 2024

A Very Awkward Holiday: When Gifting Goes Wrong

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.…

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Nov. 21, 2024

Heartbreak on the L Train: When Love Goes from Dreamy to Disastrous

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…

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Nov. 7, 2024

From Big Hair to Breakups: The Ultimate 80s Awkward Story

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…

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Oct. 24, 2024

Only Neighbors – Too Close for Comfort

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…

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Oct. 10, 2024

Vacation 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…

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Sept. 26, 2024

We Made It Awkward With An Expert: Dr. Jim Coan

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…

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Sept. 12, 2024

Linger Log Lovers.

Ever had a relationship that you just couldn’t flush? 😅 Tune into our outtakes this week’s episode about linger log lovers, where we share some hilarious behind-the-scenes moments that didn't quite make the cut. Well That Was Awkward is all about embracing the awkward, and this bit takes it to…

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Sept. 12, 2024

Stranded in Spain: When Love Goes Off the Rails

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,…

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Sept. 5, 2024

Why 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…

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Aug. 29, 2024

Butterfingers and the Bomb: An Unexpected Journey from Draft to Laughs

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…

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Aug. 22, 2024

A Hawk Came Knocking!

Ever had an unexpected guest at your door? 🦅 In this clip from "Well, That Was Awkward," Bree shares the story of a red-tailed hawk that decided to pay her a visit—and it’s not your typical knock at the door! Tune in as she describes the surprise, the awkwardness, and…

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Aug. 22, 2024

Baton Twirler Saves the Day! (An awkward moment from Mendy!)

🔊 What happens when a baton twirler takes matters with a cringe-y dancing dude into her own hands? 😳 In this clip from Episode 13 of 'Well That Was Awkward,' Mendy recalls the unforgettable moment when her baton saved the day during a parade! 🎺💥 Watch the full episode to…

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Aug. 22, 2024

Sebastian the Superhero: When A Good Deed Goes Wrong

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…

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Aug. 15, 2024

What Happens When One Woman's High Stakes Life Kinda Stinks

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…

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Aug. 9, 2024

Mendy's Nostalgic Crop Top Moment

When a simple T-shirt becomes a fashion statement... and a source of trouble! 😬 Enjoy Mendy’s story of transforming her cotillion tee into a crop top and the unexpected fallout. 🎙️ #Podcast #FashionFail #DIYGoneWrong #AwkwardMoments

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Aug. 9, 2024

The Good Morning Challenge #awkwardsituations #podcast

Bree’s mission to spread cheer in a quiet neighborhood took an unexpected turn! 🌅😅 Discover how cultural differences can lead to awkward (but hilarious) moments. #Podcast #GoodMorningChallenge #awkwardencounters Catch the full episode here: https://youtu.be/VbQ8s5z8Pgc?si=y_D0pe8x9eUG6oAI

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Aug. 8, 2024

From Faux Pas to Fabulous How One Girl Owned Her Unique Style

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…

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Aug. 1, 2024

The Super Awkward Elevator Episode: How to survive when you're stuck

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…

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July 24, 2024

Hot Hippie Summer: The Greatest Awkward Breakup Story Ever Told

This 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…

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July 18, 2024

Higher Math: This is your brain on Calculus

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…

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July 11, 2024

Savannah Surprise: What happens when a date gets really awkward

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 coffee, here’s the non-typoed link: Link (https://www.buymeacoffee.com/awkwardsage) • George Steele's Awkward Date: From a boring start to a fiery…

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