Well, That Was Awkward

Well, That Was Awkward

Awkward stories, big laughs, (pretty much) zero judgment. Join Mendy and Bree, your utterly unqualified awkwardness experts, as they unpack hilarious, cringeworthy moments from people like you. Get ready to say ”Oh noooo!” out loud, then secretly feel better about your own life.

Episodes

January 2, 2025 9 mins

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 titl...
Mark as Played

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 diaper rash cream miscommunications to B...

Mark as Played

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 perfect icebreaker for h...

Mark as Played

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:

  • Read more
Mark as Played

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 books they forgot they’d already read....

Mark as Played

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 ...

Mark as Played
October 24, 2024 37 mins

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 u...

Mark as Played

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 yo...

  • Mark as Played

    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 be the best thing to happen in a re...

    Mark as Played

    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 include:

    • Read more
    Mark as Played

    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!
    • Read more
    Mark as Played

    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!

    Mendy kicks off the episode with a s...

    Mark as Played

    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 recording ...
    Mark as Played

    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 awkwar...

    Mark as Played

    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 th...

    Mark as Played

    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 ep...

    Mark as Played

    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 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 n...

    Mark as Played

    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 awkw...
    Mark as Played

    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?

    Key Themes:

    • Embracing awkward moments
    • The ups and downs of dating
    Mark as Played

    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:

    Mark as Played

    Popular Podcasts

      If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

      Dateline NBC

      Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

      On Purpose with Jay Shetty

      I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

      The Bobby Bones Show

      Listen to 'The Bobby Bones Show' by downloading the daily full replay.

      The Clay Travis and Buck Sexton Show

      The Clay Travis and Buck Sexton Show. Clay Travis and Buck Sexton tackle the biggest stories in news, politics and current events with intelligence and humor. From the border crisis, to the madness of cancel culture and far-left missteps, Clay and Buck guide listeners through the latest headlines and hot topics with fun and entertaining conversations and opinions.

    Advertise With Us
    Music, radio and podcasts, all free. Listen online or download the iHeart App.

    Connect

    © 2025 iHeartMedia, Inc.