Well, That Was Awkward

In this episode of Well, That Was Awkward, Mendy and Bree bask in the hilarity of the awkward, celebrating the moments that leave us red-faced but connected. Fresh off their Best of C-Ville award win (and plotting the deviled egg party spread), they invite listeners to join their Facebook group and send in stories that prove awkwardness is universal.

This week’s story spotlights Stephanie (aka Jen), a former child star of community...

From Brad Pitt’s jewel-inlaid cowboy boots to Jennifer Aniston playfully balancing toward a stranger on a hiking trail, Well, That Was Awkward is serving up the ultimate playlist of star-studded slip-ups, blunders, and “did that just happen?” moments. Bree and Mendy swap their own cringe-meets-comedy celebrity encounters—like the time Bree sat between her husband and the last man left on her Hall Pass list (sorry, Spalding Gray), a...

Bree here. It’s 4 AM. I’ve got flour in my hair, burns on my arms, and questions about my life choices.

In this solo installment of Awkward and Alone, I share what happened when I—middle-aged arts executive, story-slinger, and resident night owl—decided to take a second job… at a bakery. Why? Because I wanted something “real.” (Spoiler: it got real fast.)

This is a tale of romanticized rout...

A dead butterfly wedding tribute.

A throuple in a walk-in closet.

An ex at the door.

This week, we hear from a listener whose spring break turned into a science-backed, champagne-fueled throuple… until his ex crashed the party.

Also:

🦋 The world’s most tragic butterfly release

📚 Sex ed memories involving cartoon nudity and romance novels

💬 Advice from a former wallflower turned botanical Casanova

Don’t open the door. Don’t shake...

Mendy’s riding solo—and taking you on a truly absurd (but 100% real) journey through amateur detective work, neighborhood drama, and a very misunderstood pair of underwear. Also featured? A severed hand, a fake penis, and one heroic fishing vest rescue.

Solving crime is awkward, y’all!

If you’ve ever felt like a badass and then watched your dignity slide down a storm drain—this one’s for you.

What do you do when someone asks you to do something you absolutely do not want to do, but they think they’re offering you an honor? This week, Bree and Mendy tackle the awkwardness of saying no when saying yes feels like a social trap. And speaking of traps, they also share a listener story that includes hiking, exotic dancers, two dudes marinated in fish slime, and one “bear” attack in the Wyoming wilderness. It’s equal parts adv...

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...

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,...

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...

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 Ch...

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...

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...

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...

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