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