The Madonna Tape Heist: Scandals and Small Town Secrets Revealed

Bree: Hi Mendy.

Mendy: Bree.

Bree: Oh, it’s so good to see you today.

Mendy: You too.

Bree: Do you have an awkward story from this week?

Mendy: Oh boy. Of course I do.

Comedy Night Mishap

Mendy: This one happened on stage, live in front of people. Denise and I were co-hosting one of our comedy nights.

Bree: Hold on. One thing first—

Mendy: What?

Bree: We need to tell our listener who Denise is because even though she’s famous to us, not everybody knows who she is.

Mendy: Yes, Denise is our best friend. We share her.

Bree: And we call her Dee Dee.

Mendy: Yes.

Bree: So you’re on stage, one of your comedy nights—by the way, fantastic comedy nights.

Mendy: Oh, thank you.

Bree: It’s been so much fun while we’ve been on hiatus to see you perform. Although, I get a little jealous because I want it to just be me—

Mendy: Up there alone, performing for everyone?

Bree: No, an audience of one. So, okay, you’re performing with Denise?

Mendy: Yes, co-hosting as the Tiptop Twins.

Bree: Who are the Tiptop Twins?

Mendy: I was afraid you were going to ask that. They’re hard to describe. They’re so unique. Do you know the show Hee Haw?

Bree: Of course.

Mendy: Imagine all those girls from Hee Haw, but a whole lot naughtier and not quite as smart—except when it comes to beauty techniques.

Bree: They’ve got beauty techniques down.

Mendy: Yeah, and our origin story is that they are our legal wards. We take care of them because they can’t function in the real world. Every once in a while the girls sneak out and get up to mischief—promoting businesses that never asked to be promoted, like firework stands and little kids’ lemonade stands.

Bree: I’m going to put a link to that video of the Tiptop Twins at the lemonade stand in the show notes. If you need a pick-me-up, go watch it. It cracks me up every time.

Unexpected Reunion

Mendy: So at this show, we’re hosting and welcoming the next comedian right after intermission. We’re doing a little bit, and in the middle of it, I look out into the audience and see my best dude friend from high school—someone I haven’t seen since I was 19. I just stop and say:

Mendy: “Jed Hurt! Jed Hurt!”

Bree: In the middle of the show?!

Mendy: Yep. “Guys, Jed Hurt is here! He’s one of the coolest dudes I’ve known!” And then we get back into it and introduce the set.

Bree: First of all, how cool is it that your best friend from high school showed up at your show?

Mendy: I was so excited to introduce him to Gabe and my friends who were there. Jed is epic.

Bree: Gabe is…

Mendy: My Siggy.

Bree: Got it.

Mendy: So I run offstage and back, and I’m like, “Oh my gosh, Jed, what are you doing here?” And then I look closer… it’s not him.

Bree: Oh no.

Mendy: Totally not him. He was a sweet, shy guy under a ball cap, grinning. The woman with him—girlfriend or sister—was cracking up. I said, “You’re not Jed. I’m sorry. You just look like someone I know.” And I bet he’s a really cool person.

Mendy: I had in my reading contact. Because when I checked the lineup backstage, I didn’t want anyone to see Tina (my Tiptop Twin) wearing glasses. They don’t age.

Bree: For our younger listeners, this is what happens when you need reading glasses but want to maintain the illusion. One contact lens for near, one for far.

Mendy: But it messes with your distance vision.

Bree: That happened because of Tina’s vanity.

Mendy: Yep.

Bree: But the beautiful thing is you got two big moments—joy thinking Jed was there, and then that delicious awkwardness.

Mendy: Exactly.

Bree: And I’m sure it made that guy’s night!

Mendy: Wherever you are, Jed Hurt, you’re still a cool guy. Give him a high five for me if you know him.

Listener’s Awkward Story – Dee Dee’s Mission

Bree: We’re keeping our episodes tight this year, so let’s go into the awkward story.

Mendy: This one’s from a listener—Dee Dee.

Bree: Our Dee Dee?

Mendy: Maybe. These are anonymous.

Bree: I know it’s gonna be good if it even resembles our Dee Dee.

Mendy: Also, it takes place in 1991.

Bree: Oh, the year I graduated from high school.

Mendy: It was the end of apartheid, the Gulf War started, and the Dow hit 3,000 for the first time.

Bree: Well, now I feel old.

Mendy: But most importantly, HBO aired Madonna: Blonde Ambition Live—the most-watched entertainment special in its history.

(And so begins the Madonna tape heist story…)

Dee Dee and Nathan’s Summer Adventures

Mendy: Dee Dee and her friend—let’s call him Nathan—were obsessed with the Blonde Ambition tour. Not the book.

Bree: Oh wait, the book came out the next year. Okay, so where were Dee Dee and Nathan?

Mendy: It’s summertime. They’re part of a small, tightly knit friend group. Dee Dee and Nathan had been friends since kindergarten.

Bree: Awww.

Mendy: He was a military kid who moved away in elementary school. She almost lost him in fourth grade.

Bree: Glad she got him back.

Mendy: Nathan was impeccably dressed, just like his mom. His mom was a Mary Kay rep and a makeup artist. Total bombshell. Dee Dee remembers her bringing Nathan by the elementary school library in an OshKosh B’gosh outfit to say goodbye.

Bree: Clarifying questions: were Nathan and his mom wearing matching OshKosh?

Mendy: No! Just both stylish. Mom wasn’t stuffing herself into toddler overalls.

Bree: Second: school library or public?

Mendy: School. Only you would ask that.

Bree: It matters!

Mendy: Dee Dee was gifted and mischievous, so her fourth-grade teacher basically got her out of class with a “job” shelving books. She’d go to GT in the morning, then work in the library while the other kids learned times tables and plate tectonics.

Bree: That reminds me of when I told my mom Clan of the Cave Bear was on my summer reading list…

Fifth Grade Drama Club + The Return of Nathan

Mendy: This trend continued. In 5th grade, she started a drama club in the school basement with the other misfit smart kids. They had to turn ’80s health campaigns into instructional skits—Just Say No, Get in Shape Girl, Stranger Danger…

Bree: Oh wow.

Mendy: Nathan returns in 7th grade. Still stylish. Still himself—only taller.

Bree: Still in OshKosh?

Mendy: Upgraded to Benetton. Still rolled his eyes, had lots of opinions on outfits. Unfortunately, some a-holes picked on him.

Bree: Of course they did.

Mendy: In the locker room, the guys went around saying what they’d want most in the world. Most said “Heather Luck’s boobs in my face.” Nathan said, “Three Swatch watches.”

Bree: Icon.

Mendy: He would come out later, but at the time he didn’t know he was gay. Madonna was very important to him. Bookmark that.

Teen Summers & the BK Lounge

Mendy: That summer, Dee Dee and Nathan had the best time. They drove around in Dee Dee’s beastly Dodge Charger 2.2, chilled in the BK Lounge (Burger King, duh), worked jobs, and bothered each other at said jobs.

Bree: I wish we could bother each other at our jobs.

Mendy: You do bother me at mine.

Bree: Fair.

Mendy: Nathan worked at Belk. His mom was now the Estée Lauder consultant. Huge deal.

Bree: I remember the Estée Lauder counter smell. I wanted to look like Linda Evangelista.

Mendy: And when they gave us free makeovers, we looked like Vegas showgirls at 14.

Bree: Listener, you need to see Mendy’s Glamour Shots. Please send us yours—we’re making a gallery.

The Mission Begins

Mendy: When they weren’t working, they were bothering Theresa at Whataburger or Katy at the A&P. Dee Dee remembered riding around in Jed’s grandpa’s car with handicap plates so they could get prime mall parking.

Bree: I never messed around before college. You’re making up for lost time for me.

Mendy: They spent so much time at Nathan’s house playing “The Board Game.”

Bree: The what?

Mendy: The board game. “It’s not whether you lose or win, it’s whether you win.”

Bree: Ah. Got it.

Nathan’s House & The Madonna Tape Heist Begins

Mendy: Nathan’s house was as meticulously put together as he and his mom. Big house on a hill, stocked pantry, always had Oreos. Dee Dee loved that pantry. Pick a day of the week—they were either at her place or Nathan’s.

Mendy: Then Nathan calls Dee Dee. He’s going to the beach with his family and needs her to record Madonna: Blonde Ambition Live on HBO.

Bree: And Dee Dee doesn’t have cable…

Mendy: Nope. Nathan does, but his mom said he’s not allowed to set the VCR to record while they’re gone.

Bree: Fire hazard?

Mendy: Allegedly. But really? Mom didn’t want Nathan watching Madonna. You can smell the homophobia of the era, even if it wasn’t said outright.

Bree: So what does Dee Dee do?

The Covert Operation

Mendy: Nathan gives Dee Dee her mission: sneak into the house while the concert airs, tape it on VHS, and get out. No evidence.

Bree: This is already my favorite story.

Mendy: She does a dry run before they leave—Nathan shows her how to use the cable box and VCR. Then the big night comes. She finds the spare key under the flowerpot by the grill.

Mendy: She’s nervous—she loves his parents, she adores that pantry. But she also feels powerful. She sneaks into the den, pops in the blank tape, queues up HBO… and presses record.

Bree: Does she watch it?

Mendy: Of course she does. It’s fabulous.

Bree: I didn’t see it live, but I saw the documentary. Kevin Costner comes backstage, tells Madonna it was “neat.”

Mendy: And she gags herself and goes, “Anyone who calls my show neat has to go.” ICON.

Bree: That reminds me of when we’d get backhanded compliments after shows—“You looked like you were having fun up there…”

Mendy: Or, “It was brave of you to be up there naked in front of everyone.” Brave for them to say that. Anyway—Dee Dee finishes recording, sneaks out, drives off.

The Fallout

Mendy: Next day, Nathan calls.

Mendy: “My mom is really mad at you.”

Bree: She knows?

Mendy: Yep. Because Dee Dee parked her very distinctive Dodge Charger 2.2 all the way up the driveway. It was light blue with a navy hood and the numbers “2.2” emblazoned on it. Loud as hell.

Bree: Our Dee Dee would never make that mistake now.

Mendy: But she had never parked in the driveway before. She always had to hike up that hill. With the family out of town, she finally treated herself to the premier spot.

Mendy: Unfortunately, Mrs. Harris—a neighbor, Dee Dee’s best friend’s cousin once removed, and also the lady who once fed her chicken tetrazzini—saw the whole thing. She casually mentioned it to Nathan’s mom after they got home. “So nice of Dee Dee to water your plants!”

Bree: Oh no.

Mendy: And that was it. Dee Dee was busted.

Bree: Did Nathan get in trouble?

Mendy: Yeah, but Dee Dee bore the brunt. She was persona non grata. Banned from the house.

Bree: Couldn’t she explain?

Mendy: Nope. The family was military, the home was a House of Honor, and Dee Dee had broken the code.

Redemption… Eventually

Bree: Did they ever make amends?

Mendy: Dee Dee didn’t even try to go back for a year. She slowly worked her way back in. Eventually Nathan came out to his family.

Bree: So he could finally watch Madonna in peace.

Mendy: And—this is sweet—Nathan’s mom reached out to Dee Dee on Facebook a few years ago and they had a lovely time catching up.

Bree: Maybe she’s using La Mer now instead of Estée Lauder.

Reflecting on the Incident

Bree: So… does Dee Dee have any advice for us and our listeners?

Mendy: Yes. She says she could’ve shortened the cold freeze with Nathan’s mom by writing an apology note. That’s the kind of thing Nathan’s mom would’ve appreciated.

Bree: Good advice.

Mendy: She also says she wishes she’d made her friend Sarah drive because Sarah had a quiet car. And… never underestimate the power of a nosy neighbor.

Bree: Facts.

Mendy: What would you have done in that situation, Bree?

Bree: Oh, I would’ve been terrified of getting caught. I think I would’ve gone straight to Nathan’s mom and made up a very honest-sounding lie. Like: “Hey, I need to record a documentary for a school project. Can I use your VCR while you’re gone?”

Mendy: Something educational?

Bree: Exactly. If I could figure out a cable-only show that sounded academic, I’d use that.

Mendy: Nathan’s mom would’ve seen right through you.

Bree: Excuse me! I was a very good daughter. A near-perfect honorary daughter.

Mendy: You’re right, you were. What about me?

Bree: What would you have done?

Mendy: Oh, I definitely would’ve gone to someone else’s house to tape it. But if it had to be Nathan’s house? Then yeah—I probably would’ve taken the pantry risk too. Because: Oreos.

Bree: A risk worth taking.

Mendy: But the yearlong ban? That would’ve been hard. His house was the social hub. That’s where the board games lived. I wouldn’t have been mad at my friends for still going over, but I’d have been so sad.

Enter: Dana

Bree: Mendy, normally in these situations, don’t you blame Dana?

Mendy: Ah, yes. Dana. My imaginary friend who exists solely to take the fall. But even Dana wouldn’t have been able to fix this one.

Mendy: I keep visualizing Dee Dee rumbling up that driveway in her 2.2, like a snack-fueled ninja on a mission. Dana would’ve also driven up that driveway. She would’ve made the same call.

Bree: Could you have said, “Oh, that was Dana’s car, not mine”?

Mendy: I could have tried. But this was a small town. Everyone knows your family tree—and your car. I couldn’t have convinced Nathan’s mom I had a cousin named Dana without someone calling my mom by sundown.

Bree: I actually do have a cousin named Dana.

Mendy: See? We should’ve blamed your Dana.

Listener Engagement & Wrap-Up

Bree: So, listener—we want to know: What would you have done in this situation?

Mendy: We’ve established she could’ve parked farther down the street, or gotten a quieter ride. But once the deed is done—how do you cover it up? Or shift the blame?

Bree: Our listeners are very smart, a little devious, and we want your input. What would you have done?

Mendy: Yes! I need tips. Because let’s be honest: one day I will do something like this.

Bree: Mendy, if you’re sneaking into someone’s house to record something on VHS in 2025, we’ve got a bigger problem.

Mendy: Well, I have snuck into your house before…

Bree: When we were home! You caught me meditating in my sauna blanket.

Mendy: I almost said hi but figured I’d wait until you weren’t covered in sweat.

Bree: Appreciated.

Mendy: Bree, remember when we used to rank awkward moments on a scale of 1 to 10?

Bree: We were terrible at it. Everyone got 9s and 10s.

Mendy: Because we relate to every story!

Bree: So, listener—your turn. Scroll down if you’re on Spotify. You can leave a comment. Just a number. One = not awkward at all. Ten = super duper awkward. It makes our day.

Mendy: You can do the same on YouTube. But not on Apple.

Bree: If you’re listening on Apple Podcasts, just… text Mendy.

Mendy: Yup. Hit me up.

Bree: Or email us: wellthatwasawkwardpodcast@gmail.com.

Gratitude & Closing Song

Mendy: Dee Dee, thank you for this story. And thank you for being such a good friend to Nathan.

Bree: Can you please find another Charger so we can roll up in it sometime?

Mendy: Thank you, Madonna, for everything you did for us.

Bree: Mendy, you can’t sing a Madonna song, but you can sing this one—

Mendy & Bree (singing):

🎶 Nathan needed to tape Madonna’s show.

His mama got freaked out and said, “Hell no!”

But Dee Dee’s ride won’t incognito…

Well, that was awkward.

So here’s a tip from us to you:

When you’re caught sneaking in in your 2.2,

Send a note to the mama’s what you gotta do… 🎶

Bree: Mendy, did you eat all my chips when you stopped by my house?

Mendy & Bree (singing):

🎶 Don’t cry for my corn tortillas.

Those were my corn tortillas.

Mama don’t preach…

Well, that was… awkward. 🎶

Post-Episode Note

Bree: Hey listener—usually our stories are anonymous, but this one came from our dear friend Denise Stewart.

Mendy: If you want to hear more of her antics, head to the show notes.

Bree: We love you, Denise.

Mendy: And we love awkward stories. Keep them coming.