Vault: First Date Fails That Should Have Ended Everything

Summary

Podcast Summary: The Bert Show

Episode: Vault: First Date Fails That Should Have Ended Everything
Air Date: April 13, 2026

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Episode Overview

This episode of The Bert Show dives into cringe-worthy, disastrous first (and second) date experiences that, against all odds, blossomed into lasting relationships. The cast and callers share stories of extreme embarrassment, bodily malfunctions, and disastrous decisions—proving that sometimes love surpasses the roughest starts. Hosts Bert, Kristin, Abby, Cassie, Tommy, and crew trade hilarious, real, and authentic stories, inviting listeners to reflect on the unpredictable, forgiving nature of romance.

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Key Discussion Points & Insights

1. Setting the Stage: The Greatest Dating Comebacks

• Host Bert introduces the theme: relationships that survived unforgivable early date disasters.

  • “I think that I have the greatest dating comeback story in the history of dating. It went so awful the first night... she never ever, ever saw him on for another date.” (01:02, Bert)

• Criterion: story must concern a deal-breaker incident within the first few dates.

  • “It has to be in that window of the easy bye bye. Because the fact that this guy’s still hanging on after this happened…it’s almost miraculous.” (02:42, Bert)

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2. The Hosts Share: Embarrassing Beginnings

The IBS Roadside Incident

• Cassie shares a “friend-of-a-friend” story of a woman on a third date, struck by IBS on a rural drive, forcing her to have a “side of the road doozer” in front of her date.

  • “She made a side of the road dooser.” (04:01, Host D)
  • “They are married today.” (04:33, Cassie)

• Commentary on attraction versus disaster:

  • “She has got to be, like, ridiculously over the top hot for him to be able to get past that on the third date.” (04:40, Bert)

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3. Listener Call-Ins: Even Worse First Dates

a. The Stand-Up That Led to Marriage (05:00 – Fred)

• Fred recounts standing up his blind date (she had scraped snow off her car to go out), leading to her swearing off him—until family pressure got them together. They’re now married with two kids.
  • “To this day, she'll say, our first date—I stood her up.” (06:37, Fred)

b. The Oyster-Induced Vomit Incident (06:48 – Suzy, Voice Disguiser)

• Suzy admits to puking on her date after a neighbor offered raw oysters. Despite this, they eventually married.

  • “At this little local place to do trivia…neighbor came up… put [raw oysters] under my face and I just threw up all over.” (07:06, Suzy)

• Bert relates:

  • “Stacy…she threw up the first two times we went out. That’s when I fell in love with her, man.” (07:22 and 07:34, Bert)

c. The Lipstick Body Art Prank (07:40 – Ray)

• Ray, painted in his sleep with makeup and flowers on his butt by his date, found the prank endearing; they’re now married with children.

  • “She painted me…with her makeup, lipstick, things like that. Flowers on my butt.” (08:11-08:14, Ray)

• The hosts marvel at her creativity:

  • “Who comes up, who’s drunk…‘Let's paint him with lipstick.’ I don’t know, but I want her in my entourage.” (08:48, Cassie)

d. Kissing the Wrong Guy, Having a Boyfriend, Still Destiny (09:00 – Jason)

• First night, Jason’s crush ends up making out with his good friend. Later, at a party, discovers she has a boyfriend, but they connect. They’re now married.
  • “As we left the bar…she’s actually making out with one of my good friends…Turns out she’s got a boyfriend as well…And now we’re married.” (09:21-09:53, Jason)

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e. The Car Accident & DUI Disaster (10:34 – Jeff)

• On the way home, Jeff’s date needs to pee; he takes a wrong turn, crashes, and gets a DUI. She calls him weeks later—they go out again.

  • “She decided…she’s got to pee real bad. So I pull off Roswell Road, go the wrong way, hit a car, get a DUI.” (10:39-10:52, Jeff)

• “Come to find out she’s the alcoholic, not me.” (11:18, Jeff)

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4. Bert’s Grand Finale: The Ultimate Poop-Pants Redemption

• Host Bert finally tells his “best comeback ever”:

  • Man, determined to impress, ignores his worsening stomach pain.

  • Leaves dinner early; on the ride home, has a major accident in the car.

  • Date drives him, odor and all, to his apartment, cares for him, stays to ensure he’s OK—and they end up hooking up that night.

    • “He goes to relieve himself just a little bit, what he thought was gonna be gas, and it wasn’t.” (12:41, Bert)
    • “She insists on walking him up to his apartment so that he’s okay…She still stays there to make sure he’s okay. And they end up hooking up that night.” (13:32-14:10, Bert)

  • “He is obligated to marry her. With Poopy Pants.” (14:12-14:24, Cassie & Bert)

  • “She is the greatest woman ever.” (14:26, Bert)

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Notable Quotes & Memorable Moments

• Bert: “That could be the greatest dating comeback story.” (04:35)
• Fred: “To this day, she'll say, our first date, I stood her up.” (06:37)
• Suzy: “I just threw up all over.” (07:14)
• Ray: “She painted me...flowers on my butt.” (08:14)
• Jason: “She’s actually making out with one of my good friends...Now we’re married.” (09:21-09:53)
• Jeff: “Pull off Roswell Road, go the wrong way, hit a car, get a DUI…She called me a couple weeks later.” (10:39-11:11)
• Cassie: “You were like, I want to hold your hair forever, baby.” (07:34)
• Bert, closing out: “She is the greatest woman ever.” (14:26)

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Noteworthy Timestamps

• 01:02 – Bert: Introduction of the dating disaster theme
• 04:01 – Cassie: IBS roadside incident
• 05:00 – Fred: Stood-up first date story
• 07:06 – Suzy: Vomiting on a first date
• 07:40 – Ray: Lipstick prank story
• 09:00 – Jason: Bar betrayal turnaround
• 10:39 – Jeff: DUI and still dating
• 12:41 – Bert: “Poop pants” redemption story
• 14:10 – Bert: The ultimate show of empathy ends in romance

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Tone & Language

Raucous, honest, and lighthearted, the episode exemplifies The Bert Show’s trademark authenticity. The crew moves easily between empathy and irreverent humor, poking fun at themselves and their listeners while celebrating the resilience of real-life love stories.

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Summary

This episode highlights how romance can spring from literal messes and mortifying moments, offering hope and hilarity to anyone who's ever experienced a date gone wrong. The stories—raw, sometimes gross, always real—remind listeners that sometimes, the most enduring relationships begin with stories better left untold…or better yet, retold on morning radio.

Transcript

[A]

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[B]

got a question to ask you guys. 404-741-Q100 I think that I have the greatest dating comeback story in the history of dating. It went so awful the first night that these two were out. It should be a no brainer that she never ever, ever saw him on for another date. But they have seen each other and it has worked out well over the last couple of weeks. I don't even want to tell you guys what the story is at. I just want you to call in and give us your I mean it's this is the greatest comeback dating comeback. We tried marriage with this a couple of weeks ago. This is like a first or second date. He or she messes this thing up so badly that there's there should be no way that you would ever see him or her ever again. But for whatever reason, out of the goodness of your heart, you're like, I'll give him one more shot. And for it, lo and behold, the second date is great and then the third date is fine and the fourth date is great and you end up in a relationship with this guy or this woman even though that first date was awful.

[C]

Does it have to be the first date that was awful or just something right at the beginning or what?

[B]

I think it's gotta be like the first or second date. And then I'll tell you what I consider to be the worst dating comeback story. Well, actually the best.

[D]

It has to be the incident has to happen early enough in the relationship that it could be a deal breaker situation. You know, like by the time you've gone out with somebody, you've gone out with somebody half a dozen times. And like, for example, whatever. They don't open the car door for you once.

[B]

Mm.

[D]

Like they've built up or whatever. But if you're on first, second, maybe

[B]

third, know each other very well, first

[D]

couple of dates, and they do something. Like if you're on the third date with somebody and he sends 20 text messages from the dinner table, then you're gonna. You might be like, I got nothing invested in this. I've been out to dinner with him twice now. It's the third time done. Bye bye. So it has to be in that window of the easy bye bye. Because the fact that this guy's still hanging on after this happened, which was in that easy bye bye period, I mean, it's almost miraculous. I think there should be a bronze bust of him somewhere in some sort of museum with the story.

[C]

I have one that I could maybe get it started with.

[B]

Okay. 404-741-Q100. Because it cannot beat the one I'm about to tell you.

[C]

This is a friend of a friend. So this is one of my best friend's high school friends that this happened to. She was on her third date and he had taken her to a nice restaurant. They live in sort of a small town. So there's like, you know, the, you know, like sort of the more chain restaurants like the Chili's or the Olive Gardens or whatever. And they had done that for the first two dates. But he wanted to take her somewhere special for their third date. So they were about 40, 45 minutes away to this restaurant. And as they have scared. Great dinner, whatever. They're driving back from the restaurant. She realizes she has a little IBS, like about 20 minutes into the trip and literally had to make him pull over. And she had a.

[D]

She made a side of the road dooser.

[B]

A side of the road doo. That one may be better than the one that I'm about to tell.

[C]

And guess what? They're married now.

[B]

Whoa. That one may be better than the one I'm about to tell you.

[C]

Really?

[B]

It's close. They're Very, very similar, actually. I don't even think I could ask

[A]

to pull over and say that.

[B]

So on the side of the road,

[C]

she said there was no choice. She had no other options. She just told him to pull over.

[B]

And they are married.

[C]

They are married today.

[B]

Okay. That could be the greatest comeback dating comeback story.

[C]

Cause this is, you know, a high school friend of one of my best friends that I don't know. And in my mind, I thought, she has got to be hot. Like, she has got to be, like, ridiculously over the top hot for him to be able to get past that on the third date.

[B]

Wow. Good morning. Here is. I'm not sure who. Good morning, Q and A.

[E]

Hey, good morning. This is Fred.

[B]

Hey, Fred.

[E]

How you guys doing?

[C]

Good.

[B]

What's up, man?

[E]

Good. I love the show. I don't know if this is like the most horrible story in the world, but I'll lay it out for you guys. We were living up in New Jersey at the time, and a mutual friend of ours had, you know, set us up. And we had talked a few times on the phone and decided to give it a shot and go out, you know, blind date type thing. So we had set something up. In my impression I was going to call her on like, a late Sunday afternoon and, you know, see how we both felt. Maybe go out on Sunday night, you know, kind of make it kind of easy. The first date, she was under the impression that we definitely had a date. Okay. So Sunday comes along and I was

[F]

doing some odd jobs, my dad and

[E]

stuff on the weekends, and I was exhausted and it was snowing, and I'm like, yeah, I'm not, you know, this isn't ideal for first date. So I called her up around, must have been about 6, 6:30. And, you know, I'll say she's all excited. And I'm like, yeah, you know, I worked all day. I'm like, dad, I can't. You know, I'm not. I'm just not up for this. And, you know, let me give you a call Thursday. We'll set something for next week. And she was fine on the phone and, you know, call me. And then so I later find out, you know, she goes back inside to her mom. Now she. She was dressed up for the date. She had scraped the snow and ice off her car. I mean, she was set to go. And she goes back in. She's like, mom, I don't care if, you know, Uncle Frank is setting us, you know, I am not seeing this guy. And her mom was like, no, no, no, it's Frank. You have to. You know, he was like the Godfather type Italian. And so lo and behold, you know, we go out a few more times and it's great. And you know, here we are X years later, we have two kids, married and all that stuff. So it ended up great. But to this day, she'll say, our first date, I stood her up.

[B]

Okay, stand up on a first date. And then ends up married to Gary with two kids. He said, Good morning, Suzy, you're on Q100. Hi, how are you?

[G]

Good, how are you?

[B]

Great. You were on the Voice Disguiser. It really must be bad.

[G]

Oh, it's bad. I started my first date, I was 18 years old and I was so nervous. So I decided we met at this little local place to do trivia and I decided to start drinking some beer to take the edge off. So at the end of the night we go back to his parents house and his neighbor came up to me with some raw oysters and put them under my face and I just threw up all over.

[C]

Oh no.

[G]

Oh man, it's so bad and it's so ironic cause we actually ended up getting married.

[C]

Oh.

[B]

See, Stacy. When I started dating Stacy, she threw up the first two times we went out.

[C]

The first two times?

[B]

Yeah. We were drinking so much that she ended up puking both times we went out.

[D]

That's funny.

[B]

That's when I fell in love with her, man.

[C]

You were like, I want to hold your hair forever, baby.

[B]

That's my girl right there. Hey, Ray. Good morning. You're on Q100.

[C]

Hi.

[E]

Hey guys.

[B]

Hey.

[F]

Crazy date story. My first date with this girl, we

[E]

had been friends for a while.

[F]

She invites her friends, she gets drunk, we go back to my hotel. She ends up passing out, middle of

[E]

the night, wakes up, paints me, puts

[F]

paints a flower on my butt, takes pictures and sends it to her friends

[E]

to mock me out.

[F]

We're now, we're now married with children.

[C]

No.

[B]

You're mad. Are you kidding? You got over that.

[C]

Wait a second. What did she do to you?

[F]

She painted me. With what?

[E]

Her makeup, lipstick, things like that.

[F]

Wore paint on my face, flowers on my butt.

[B]

Did you pass out? I mean, were you like hammered, passed out?

[E]

Me?

[F]

No, it was just like five in

[E]

the morning and then up all night. Flying. Yeah, it was.

[F]

I was out at some point. I probably woke up.

[E]

Thought she was just like giving me

[F]

a massage or, or something. Or rubbing my back. Yeah, she was painting me.

[C]

That's awesome. That is hilarious.

[B]

And again, this goes with. She must be super Hot, Obviously, he married her, so she's super hot, or you can never get away with that.

[C]

I like his wife already, because who thinks of that?

[D]

Somebody used hammers.

[C]

Who comes up, who's drunk? I've got an idea. I just met this guy. Let's paint him with lipstick. I don't know, but I want her in my entourage.

[B]

Jason, greatest dating comeback of all time.

[F]

Well, it's pretty good. It's, you know, the first night we met, we didn't know each other. My friends were out and her friends were out or downtown Atlanta. And of course, we all ended up running into each other in the bar, and her and I talked the entire night. And as we left the bar that night, I turned around, and she's actually making out with one of my good friends.

[C]

Oh, God.

[F]

So then I like her, too. Yeah, exactly. So then I got invited to a party by one of her friends a week or two later. You know, we hadn't talked since, and so I ran into her at a party, got to the party. It turns out she's got a boyfriend as well.

[D]

Hello.

[F]

So. But the entire night, we spend these talking to each other again, and she. I didn't even know her boyfriend was there at the time. She never talked to him once that night. But it went well. And now we're married.

[G]

Wow.

[F]

It's kind of an interesting story. I never would have expected, you know, that. That result after the first night.

[D]

Do you tell. Like, how close do you have to be with friends before you start to share these stories? All the people that ended up married together, like, war, pain on your butt, dude, and stuff. Like, how well do you got to know your. You know, whatever.

[C]

After what anniversary is it cool to tell those stories at parties?

[B]

Because you've been lying for years.

[D]

Right?

[G]

Right.

[B]

I feel for that last guy because there's nothing worse than, as the guy putting in all the time, all night long, trying to hook up with one girl, and then one of your friends comes, and in a second, your night is over, and he hasn't put any time in at all. And he gets. The girl sucks.

[C]

Poor dude.

[B]

Jeff, you're on Q100. Hi.

[E]

Hey, man.

[F]

How you doing?

[B]

What's happening, man?

[F]

I was on a date with this chick, went downtown, coming back, and she decided, you know, she's got to pee real bad. So I pull off Roswell Road, go the wrong way, hit a car, get a dui.

[C]

Oh, no.

[F]

I'm in the back of the car, going to jail. She's crying because she doesn't know how she's gonna get home?

[C]

Oh,

[F]

I was fine. I mean, I. I'm not worried about you.

[B]

DUI and an accident, and that's the first date and you guys end up continuing to go out.

[F]

Yeah, she called me a couple weeks later. We ended up going out. I don't know why.

[D]

When she got out of jail. Yeah.

[F]

Come to find out she's the alcoholic, not me.

[B]

That's why she's like, you really wasn't that bad. What's a.25?

[D]

I think she's OBL. I think she's obligated to go out with him again because she's the one who made him pull over to pee. So, like, it's her kind of. Her fault that he got off, you know, I mean, his fault. He turned the wrong way, run into a car and got a dui. That's his fault. But she could have, you know, if she had a bigger bladder, none of that would have happened.

[F]

Come on.

[B]

The one I was gonna share is similar to Jen's, except Jen's, I think, is actually better. And I can't use names here, but they are out on a first date. And the guy. First date, very first date. And he's been jockeying to get a date her for quite a while. And finally she gives in and he goes all traditional on her where he picks her up and does all that. Actually, I think for whatever reason, no, it was his car. So he picks her up, but he's got, like, this stomach crampy thing going on beforehand. But she's just so hot that he's like, there's no way. I mean, I could suck it up through this thing and things will be fine. So they go out on their date, and while they're at dinner, his stomach starts to do the grumble thing you're talking about. And he's like, I gotta be totally honest with you. We gotta get outta here. I didn't feel good when this date started, and my stomach's jacked up now. We gotta split. It's so bad. And he's cramping up so bad that she has to get in his car and start driving him home.

[C]

Ooh.

[B]

So on the way home, he goes to relieve himself just a little bit, what he thought was gonna be gas, and it wasn't.

[D]

Oh, boy.

[G]

Oh, no.

[C]

That story is worse because she had to endure the odor and everything. Where Jen's friend. The guy didn't. The guy didn't know. She just got out of the car.

[B]

She got out of the car.

[F]

What?

[B]

So it happens in the. While he's in his own passenger seat. He said it was awful. And he rolled. He rolled down the window. It was like one of those don't say anything, don't tell type deals. Like, he knew she knew, but nobody was saying anything.

[C]

Do you think she could have thought it was really bad gas?

[B]

He said that he was doing everything that he could to get that smell out of the car. Like, he rolled down the window and he put his Position himself in the passenger seat to where his booty would be like, in the window.

[C]

You're kidding me.

[B]

It wasn't a little. It was a lot.

[C]

Oh, that makes it worse.

[B]

And here's the comeback part. Because she drives him home, you know, he doesn't say what happened, but she's like, he's doubled over in pain. So she insists on walking him up to his apartment.

[C]

He's okay.

[B]

So that he's okay. They get up to the apartment. He just assumes she's gonna bail once he's inside the house. But she's like, the real comforting type. So he gets inside the apartment and goes in, takes a shower, cleans everything off, lays down. She still stays there to make sure he's okay. And they end up hooking up that night.

[C]

No way.

[B]

Yes.

[D]

He has to marry her.

[B]

Best comeback ever in the history of dating.

[D]

He is obligated to marry her.

[C]

With Poopy Pants.

[B]

He is obligated to marry her.

[D]

That's him.

[B]

She is the greatest woman ever.

[C]

Oh, God. Man. Poop God.

[B]

The Bircho.