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 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 Charger.

It’s a tale of forbidden pop culture, nosy neighbors, teenage code-breaking, and the long road back into a small-town mom’s good graces. Plus, the Tiptop Twins make an appearance, Mendy mistakes a stranger for her high school BFF, and Bree confesses to reading Clan of the Cave Bear for “extra credit.”

Episode Breakdown

• 🎤 Comedy night awkwardness & Tiptop Twins misidentification
  
  
• 📼 Dee Dee’s undercover mission to record Madonna
  
  
• 🚗 A loud car, a flowerpot key, and one overly observant neighbor
  
  
• 🧃 Pantries, Belk makeup counters, and teenage friendships under fire
  
  
• 💌 Advice on apologies, VHS ethics, and what we’d all do differently now
  
  

Guest Mention

Denise Stewart is a longtime friend, performer, and mischievous mastermind behind some of the Tiptop Twins’ best moments. You can find more about her and her work on her site or via@swamphatchedbutterfly.

Links Mentioned

• 🎥 Tiptop Twins at the Lemonade Stand: Watch on YouTube 
• 📧 Email your awkward story: wellthatwasawkwardpodcast@gmail.com
• VOTE FOR US!!! https://bestof.c-ville.com/2025/podcast
• Check out Mendy's Glamour Shots! https://www.youtube.com/watch?v=43u4Cle7Pd0
• 💬 Comment on Spotify or YouTube! Rank the awkwardness 1–10
  
  
  

Call to Action

Tell us: What would you have done in Dee Dee’s shoes? Sneakier alibi? Different car? Throw Dana under the bus? Text Mendy, comment on Spotify, or send us an email. We’re collecting strategies for future VHS emergencies.

🔗 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
  
  
• 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!