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 strangely endearing. Tune in for laughs, relatable moments, and reassurance that no matter how awkward things get, you're never alone.

In This Episode:

• Bree's existential closet musings: Why is her wedding photo tucked away next to old shoes?
• Why getting married at 22 might not have been her brightest decision, but, hey, it took!
• Bree’s swanky (but actually super sketchy) engagement party at the Plaza Hotel.
• The legendary appearance of Nikolai, the ex who crashed Bree’s ceremony in a clown nose.
• The epic "Linebacker-Hemingway Minister vs. Party Clown Ex" showdown at the after-party.
• The awkward and ultimately sweet moments that defined Bree's uniquely chaotic wedding.

Call to Action: Awkward wedding tales unite us all—what's yours? Send your wonderfully weird stories our way, and you just might hear them featured in a future episode!

• Share your own awkward story (Anonymously or not!) via the WTWA Form
• Leave us a voice memo on the WTWA Website
• Follow us on Instagram: @awkwardsagemedia
• Support the show at Buy Me A Coffee
• Save 10% on your Monk Manual at monkmanual.com/AWKWARD using code AWKWARD

You’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 all.

As always, we’ll celebrate the awkward, embrace the unexpected, and ask ourselves the most important question: What would Dana do?

In This Episode:

• Re-entering the dating world post-lockdown
• Astrology-fueled chemistry
• Velvet couches and questionable cocktails
• Queer joy, hope, and heartbreak
• The ultimate awkward moment—and how to recover

Listener Advisory:

Contains adult themes, queer dating mishaps, mild swearing, and irreverent woo.

• Share your own awkward story (Anonymously or not!) via the WTWA Form
• Leave us a voice memo on the WTWA Website
• Follow us on Instagram: @awkwardsagemedia
• Support the show at Buy Me A Coffee
• Save 10% on your Monk Manual at monkmanual.com/AWKWARD using code AWKWARD

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 painfully relatable tale about boundaries, intentions, and how quickly friendliness can get misread.

In This Episode:

• Why Bree can’t join this week’s episode (yep, it’s TMI in the best way)
• How Mendy’s beloved 4Runner set the stage for a flirtatious disaster
• The misunderstood meaning of “detailing” and how it got her into trouble
• A spontaneous rap battle that blurred the line between play and pursuit
• The moment Mendy realized: “Oh no. This man thinks I’m into him.”
• How she owned the moment—and shut it down

Call to Action:

Ever had a “wait, was that flirting?” moment? Or a flirty moment you really didn’t ask for?

Share your story with us! Use the submission link in the show notes or head to https://www.awkwardsagemedia.com/show/well-that-was-awkward-podcast/ You might hear it on a future episode!

Credits:

Host + Writer: Mendy St. Ours

Producer + Editor: Bree Luck

A production of Awkward Sage Media

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, teenage code-breaking, and the long road back into a small-town mom’s good graces. Plus, the Tiptop Twins make an appearance, Mendy mistakes a stranger for her high school BFF, and Bree confesses to reading Clan of the Cave Bear for “extra credit.”

Episode Breakdown

• 🎤 Comedy night awkwardness & Tiptop Twins misidentification
• 📼 Dee Dee’s undercover mission to record Madonna
• 🚗 A loud car, a flowerpot key, and one overly observant neighbor
• 🧃 Pantries, Belk makeup counters, and teenage friendships under fire
• 💌 Advice on apologies, VHS ethics, and what we’d all do differently now

Guest Mention

Denise Stewart is a longtime friend, performer, and mischievous mastermind behind some of the Tiptop Twins’ best moments. You can find more about her and her work on her site or via@swamphatchedbutterfly.

Links Mentioned

• 🎥 Tiptop Twins at the Lemonade Stand: Watch on YouTube
• 📧 Email your awkward story: wellthatwasawkwardpodcast@gmail.com
• VOTE FOR US!!! https://bestof.c-ville.com/2025/podcast
• Check out Mendy's Glamour Shots! https://www.youtube.com/watch?v=43u4Cle7Pd0
• 💬 Comment on Spotify or YouTube! Rank the awkwardness 1–10

Call to Action

Tell us: What would you have done in Dee Dee’s shoes? Sneakier alibi? Different car? Throw Dana under the bus? Text Mendy, comment on Spotify, or send us an email. We’re collecting strategies for future VHS emergencies.

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.

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.

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.

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.)