Episodes
July 31, 2025
When it Comes to LOVE, Three is the Awkward Number… Or Is It?
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 part...
July 24, 2025
She Found Her Stolen Car… With a Psychic Hunch and a Booby Trap
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...
July 17, 2025
Bear With Us — These Might Be the Worst Camping Decisions Ever
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 i…
July 10, 2025
I Got Married at 22 and Invited My Ex -- Here's the Awkward Truth
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...
July 2, 2025
Why You Should Never Date During Mercury Retrograde
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 vi...
June 26, 2025
Awkward Confession: The Accidental Affair
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...
June 19, 2025
The Madonna Tape Heist: Scandals and Small Town Secrets Revealed
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...
Jan. 2, 2025
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 recoun...
Dec. 19, 2024
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 unexpect...
Dec. 12, 2024
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, ...
Dec. 5, 2024
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 hier...
Nov. 21, 2024
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...
Nov. 7, 2024
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! Br...
Oct. 24, 2024
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,...
Oct. 10, 2024
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 unforgettabl...
Sept. 26, 2024
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 Neur...
Sept. 12, 2024
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 d...
Sept. 5, 2024
Why We're Hitting Pause on Weekly Episodes (Spoiler: It’s Awkward)
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 episod...
Aug. 29, 2024
Butterfingers and the Bomb: An Unexpected Journey from Draft to Laughs
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 hilariou...
Aug. 22, 2024
Sebastian the Superhero: When A Good Deed Goes Wrong
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!
Aug. 15, 2024
What Happens When One Woman's High Stakes Life Kinda Stinks
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 chil...
Aug. 8, 2024
From Faux Pas to Fabulous How One Girl Owned Her Unique Style
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 s...
Aug. 1, 2024
The Super Awkward Elevator Episode: How to survive when you're stuck
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, particular...
July 25, 2024
Hot Hippie Summer: The Greatest Awkward Breakup Story Ever Told
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…