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 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.)

🔗 Connect with us:

• 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
• Send us an email: wellthatwasawkwardpodcast@gmail.com
• Support the show at Buy Me A Coffee
• Save 10% on your Monk Manual at monkmanual.com/AWKWARD using code AWKWARD

Don’t forget to follow the show wherever you listen!