Well, That Was Awkward

How 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 this season.
Details on how to share your awkward stories to be featured in Season 2!
Connect With Us:
🎙️ Share Your Awkward Story:
Submit your story anonymously (or not!) through the Well That Was Awkward Story Form
📞 Leave a Voicemail:
Call our SpeakPipe line to share your awkward moments directly: Leave a message!
Facebook Group: Well, That Was Awkward Facebook Group
Instagram: @AwkwardSageMedia
Email us: wellthatwasawkwardpodcast@gmail.com 
📰 Follow Us on Substack:
Stay updated with our awkward adventures and more! Subscribe here: Awkward Sage Substack
☕ Buy Us a Coffee:
Support the podcast and fuel our awkwardness: Buy Us a Coffee
 
Thank You for Listening!
We’re so grateful to our listeners for making this season unforgettable. Season 2 will be back in the spring, packed with fresh awkwardness and even more laughs. In the meantime, keep sharing your stories, stay awkward, and we’ll see you soon!
Don’t forget to click “Follow” on your podcast platform so you don’t miss Season 2.
Credits:
This has been an Awkward Sage Production.

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, 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 touching yet utterly ridiculous holiday tale.
 
What’s Inside This Episode?
Mendy’s Underwear Mishap: A locker room incident involving going commando and scratchy jeans.
Bree’s Glasses Dilemma: Why Bree sometimes feels invisible in glasses (and sunglasses).
Melody’s Christmas Chaos: A listener story about an unforgettable Christmas morning featuring a casserole, Uncle Steve’s antics, and a surprise visit from the Grim Reaper.
Grandma’s Grand Exit: How Melody’s family handled grief, awkwardness, and the inevitable with laughter and a holiday breakfast.
Final Reflections: Bree and Mendy discuss the beauty of awkwardness, the humanity in grief, and the hilarity of family dynamics.
You can now play Well, That Was Awkward: The Party Game with your own family! Create new memories… or at least new grudges. Get it here.
 
**A special thanks to “Melody” for sharing her incredibly awkward story.**
Want to share your own awkward story? Submit your cringe-worthy, hilarious, or heartwarming moments anonymously (or not!) here.
 
Connect with Us
Share your thoughts on Grandma’s casserole, Uncle Steve’s holiday flair, or anything else awkward with Bree and Mendy!
Instagram: @awkwardsagemedia
Website: https://www.awkwardsagemedia.com/show/well-that-was-awkward-podcast/
Buy Us a Coffee: Support the podcast at Buy Me a Coffee.
Get your own Monk Manual with a discount! Visit Monk Manual and use code AWKWARD.
Next Episode Preview
We’ll be back in January with another episode packed with laughter, insights, and unexpected twists.

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 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 link below to grab your free copy of Well, That Was Awkward, The Party Game:
👉 Download Here
 
Connect With Us:
•Share your awkward game stories with Bree and Mendy at Well That Was Awkward.
•Follow us on Instagram: @awkwardsagemedia
•Join our private Facebook group to exchange stories and connect with other awkward enthusiasts.
 
Closing Note:
This game guarantees a hilariously awkward holiday season in the best way. So what are you waiting for? Download the game, play it, love it, and share the awkwardness with us!
Remember, you may be awkward, but you are definitely not alone.
 
This episode was brought to you by Awkward Sage Media.

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. 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 (loaded questions, anyone?).
Holiday survival tips: Bree and Mendy’s thoughts on keeping the peace… or burning it all down (metaphorically, of course).
Why family dynamics and plastic tumblers just don’t mix: A WASP’s guide to handling cringe-worthy gifting inequalities.
If this episode doesn’t have you simultaneously laughing and clutching your chest in chagrin, we don’t know what will.
Got your own awkward holiday tale? Spill it here: https://www.awkwardsagemedia.com/show/well-that-was-awkward-podcast/about/ 
Or better yet, record a voice memo! We’d love to share your horror (oops, we mean holiday) stories in a future episode. You can share it anonymously HERE or email it to wellthatwasawkwardpodcast@gmail.com 
BONUS: You can now play Well, That Was Awkward: The Party Game with your own family! Create new memories… or at least new grudges. Get it here.
Feeling overwhelmed this season? The holidays can be tough. If you’re struggling, help is always available. Call or text the Suicide & Crisis Lifeline at 988 to connect with someone who cares.
Stay connected:
Follow us on Instagram: @awkwardsagemedia
Support the show: Buy Me a Coffee
Share your story: https://www.awkwardsagemedia.com/show/well-that-was-awkward-podcast/about/
Let’s face it, you may be awkward, but at least you’re not gifting pizza scissors to your stepson. (Probably.)

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 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 definitely not alone!
What You’ll Hear:
A listener’s dramatic story of first love and heartbreak, complete with theater boys, Snapchats, and questionable restaurant choices.
Bree’s nerd date gone wrong—and why you should always double-check where your laptop is.
The moment Mendy and Gabe conquered their homebody tendencies… only to encounter an awkward dance floor moment.
Why theater boys might not always be worth the drama (and when to walk away).
Breakup advice, the best ice cream for heartbreak, and the joy of awkwardness.
Connect with Us:
Share your awkward stories (Anonymously – or Not!) in writing or by voicemail at Awkward Sage Media
Join our Cult of Awkwardness on Facebook – We want to get awkward with you! Facebook Group
Follow us on Instagram: @awkwardsagemedia
Buy us a coffee and support this podcast at Buy Me a Coffee
Get a discount on your Monk Manual at Monk Manual using the code AWKWARD.
Friends, this podcast is possible because of your awkward moments -- so please share them with us! Questions? Email us at wellthatwasawkwardpodcast@gmail.com or hop on over to Instagram and leave us a DM! 

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 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 & Jason Bateman (Silver Spoons), MacGyver, George Clooney, Tom Selleck
We want to hear from you!
Got your own misheard lyrics? We want to hear them! Whether it’s a song you sang all wrong or a lyric that took on a whole new meaning, share your funniest misheard lyrics with us. You can even sing them on our Speakpipe and make us laugh out loud! We’ll be sharing our favorites in our Facebook group, so don’t miss out on the fun. Who knows? Your lyrics might just make it into the next episode of Well, That Was Awkward!
 
Connect with Us:
Share your awkward stories (Anonymously – or Not!) in writing or by voicemail at Awkward Sage Media
Join our Cult of Awkwardness on Facebook – We want to get awkward with you! Facebook Group
Follow us on Instagram: @awkwardsagemedia
Buy us a coffee and support this podcast at Buy Me a Coffee
Get a discount on your Monk Manual at Monk Manual using the code AWKWARD.
Remember to click follow wherever you listen to your podcasts and join us next time for another episode filled with laughter, insights, and unexpected twists. You may be awkward, but you are definitely not alone.

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 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 act and lived a double life.
Mendy’s hilarious confession of avoiding her neighbor while under the influence of edibles. (P.S. You can listen to the episode where Bree showed up inadvertently under the influence of THC HERE.)
Jack's awkward dilemma when he accidentally catches his neighbor putting on a rather revealing show.
The episode explores the sometimes-awkward realities of being neighbors, handling embarrassing situations with humor, and offering some practical advice on how to politely address uncomfortable scenarios. Plus, we discuss the value of being upfront (or...maybe a little vague) when things get awkward.
 
Connect with Us:
Share your awkward stories (Anonymously – or Not!) in writing or by voicemail at Awkward Sage Media
Join our Cult of Awkwardness on Facebook – We want to get awkward with you! Facebook Group
Follow us on Instagram: @awkwardsagemedia
Buy us a coffee and support this podcast at Buy Me a Coffee
Get a discount on your Monk Manual at Monk Manual using the code AWKWARD.
Remember to click follow wherever you listen to your podcasts and join us next time for another episode filled with laughter, insights, and unexpected twists. You may be awkward, but you are definitely not alone.
Remember to click follow wherever you listen to your podcasts and join us next time for another episode filled with laughter, insights, and unexpected twists. You may be awkward, but you are definitely not alone.

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 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, Shaneisha Wofford and our anonymous callers, we love your awkward stories.
 
About Shaneisha Wofford:Shaneisha Wofford, JD, MA, is a fourth-year graduate student pursuing her doctorate in clinical psychology. A passionate resource to her community, she navigates life awkwardly but adventurously as an introvert who often finds herself wrapped in books and research. Shaneisha’s love for curiosity fuels her daily goal of positively impacting at least one person per day. Follow her story on Instagram.
You can find out more about Shaneisha’s journey on her Instagram @nemos_journey, or visit our full website for more information about her.
Connect with us:
Share your awkward stories with Bree and Mendy! Submit anonymously or not through the Well That Was Awkward form.
Follow us on Instagram: @awkwardsagemedia
Leave us a voice memo or thoughts on Dana’s advice through the Well That Was Awkward Website!
Support us by buying a coffee at Buy Me a Coffee
Get your Monk Manual with a discount at Monk Manual using code AWKWARD.
We’ll be back next time with more awkward stories—remember to hit follow and join us for more unexpected laughs!
 

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 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 shape relationships in unexpected ways. With a background in affective neuroscience, Dr. Coan brings academic expertise to the emotional territory we all know too well but rarely understand.
Key Topics:
The definition and role of awkwardness in relationships
Personal awkward moments, including Dr. Coan's "Car Kiss" story
How discomfort and vulnerability build emotional bonds
Navigating the blurred lines between cringe and connection
How awkward moments can lead to deepening relationships and personal growth
Guest Info: Dr. Jim Coan is a professor of psychology at the University of Virginia and director of the Virginia Affective Neuroscience Lab. He’s also the host of the podcast Circle of Willis, where he explores the brain and emotion through interviews with scientists, researchers, and thought leaders. You can listen to Circle of Willis at circleofwillispodcast.com or find it wherever you listen to podcasts.
Links Mentioned:
Watch Mendy's stand-up sets on YouTube: https://www.youtube.com/channel/UCrJI1b-eCqCKV-5KqlNtl1w
Listen to Dr. Coan's TED Talk on handholding: https://www.youtube.com/watch?v=1UMHUPPQ96c
Explore Dr. Coan's podcast, Circle of Willis: circleofwillispodcast.com
Connect with Us:
Share your awkward stories (Anonymously – or Not!) in writing or by voicemail at Awkward Sage Media
Join our Cult of Awkwardness on Facebook – We want to get awkward with you! Facebook Group
Follow us on Instagram: @awkwardsagemedia
Buy us a coffee and support this podcast at Buy Me a Coffee
Get a discount on your Monk Manual at Monk Manual using the code AWKWARD.
Remember to click follow wherever you listen to your podcasts and join us next time for another episode filled with laughter, insights, and unexpected twists. You may be awkward, but you are definitely not alone.
Remember to click follow wherever you listen to your podcasts and join us next time for another episode filled with laughter, insights, and unexpected twists. You may be awkward, but you are definitely not alone.

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, 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, no job, and no backup plan.
A sweet moment of redemption when Matthew’s professor offers him a life-changing opportunity.
We want to take Well,That Was Awkward all over the world! So we're selling T-shirts (and other merch), just like Matthew -- Get your awkward merch here: https://www.awkwardsage.com/productionservicesstore/merch
References:
Check out Bree’s high school friend, Nancy (Hilliard) Joyce’s website. Nancy was cool in high school, but she’s phenomenal now! Here’s her website: Nancy Hilliard Art
You can find Nancy on Instagram athttps://www.instagram.com/nancyjoyceart/
Connect with Us!
Share your awkward stories (Anonymously – or Not!) in writing or by voicemail at Awkward Sage Media
Join our Cult of Awkwardness on Facebook – We want to get awkward with you! Facebook Group
Follow us on Instagram: @awkwardsagemedia
Buy us a coffee and support this podcast at Buy Me a Coffee
Get a discount on your Monk Manual at Monk Manual using the code AWKWARD.
Remember to click follow wherever you listen to your podcasts and join us next time for another episode filled with laughter, insights, and unexpected twists. You may be awkward, but you are definitely not alone.
Disclaimer: This podcast is for entertainment purposes only. Please, dear listener, do not look to this podcast for relationship or financial advice. We don't know what we're talking about!!!
Correction: When Bree followed up with Nancy Hilliard to get her permission to be mentioned in this episode, Nancy clarified that she did NOT have permission to be in the smokehouse. Oops! Hope we don't get you in trouble, Nancy!