All Episodes

December 5, 2024 39 mins

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:

Let’s face it, you may be awkward, but at least you’re not gifting pizza scissors to your stepson. (Probably.)

🔗 Connect with us: Don’t forget to follow the show wherever you listen!
Mark as Played

Advertise With Us

Popular Podcasts

Stuff You Should Know
Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

The Male Room with Dr. Jesse Mills

The Male Room with Dr. Jesse Mills

As Director of The Men’s Clinic at UCLA, Dr. Jesse Mills has spent his career helping men understand their bodies, their hormones, and their health. Now he’s bringing that expertise to The Male Room — a podcast where data-driven medicine meets common sense. Each episode separates fact from hype, science from snake oil, and gives men the tools to live longer, stronger, and happier lives. With candor, humor, and real-world experience from the exam room and the operating room, Dr. Mills breaks down the latest health headlines, dissects trends, and explains what actually works — and what doesn’t. Smart, straightforward, and entertaining, The Male Room is the show that helps men take charge of their health without the jargon.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.