Boomers on the Edge
Before smartphones. Before social media. Before anyone thought to record the evidence.
Boomers on the Edge is a weekly storytelling podcast where two lifelong friends revisit the wild, reckless, and often unbelievable adventures of their youth. Kenn and Ron trade stories from the 60s, 70s, and 80s — the mischief, the bad decisions, and the close calls that somehow didn’t kill them.
From gritty Detroit bars and summer days on the lake to high school locker rooms and blue-collar job sites, every episode blends sharp improv, vivid memories, and outrageous true tales.
It’s unfiltered nostalgia — raw, irreverent, and laugh-out-loud funny.
If you like your comedy honest, slightly inappropriate, and full of “there’s no way that really happened” moments… welcome to the edge.
Boomers on the Edge
The Drive-In Date
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Kenn, Ron, and guest host Randy dive into a hilarious “coming-of-age” episode of Boomers on the Edge, as Ron recounts the unforgettable—and awkward—story of one of his very first drive-in dates.
Known back then as a clean-cut student and class president, Ron admits his dates usually leaned more toward conversations about academics and the National Honor Society than anything remotely romantic. Looking to change his luck, he seeks advice from the school quarterback on which girls might be a little more… adventurous.
After asking out one of the recommended girls, Ron quickly realizes he may be in over his head—especially when her overly enthusiastic family greets him like he’s the perfect gentleman, leaving him feeling a bit guilty about his true intentions.
Things escalate fast once they arrive at the local drive-in. Before he can even settle in, she slides across the wide front seat of his classic ’61 Cadillac and makes her move. But instead of sparks flying, Ron finds himself overwhelmed by clouds of hairspray, layers of makeup, and a situation he’s clearly not ready for.
Needless to say, the night doesn’t go quite as planned.
Kenn and Randy can’t help but laugh as Ron relives this awkward, eye-watering misadventure—proving once again that some lessons in life come with a lot of humor (and a little discomfort).
Another classic and comical memory from Boomers on the Edge!
- Adult themes and language.
- Boomer rating: Over the Edge
https://www.boomersontheedge.com
boomers@boomersontheedge.com
Hey, and welcome to Boomers on the Edge. Some guys in their 60s who still think they're 60. Your hosts, Kat and Ron. And this week's guest host, my brother, Randy. Let's get started.
SPEAKER_00Hey guys. Uh Boomers on the Edge to come at you. Ron, wasn't there an episode with you and a girl who you were kind of trying to, you know, like the high cot karate commercials trying to fight off? Um Yeah, yeah.
SPEAKER_01Yeah. It you know, in it, you know, we were talking about uh in one of the other episodes, the the lipstick from you know grandma grandma and stuff, and it kind of comes not so much grandma into the story, but full circle. But put the memories of lipstick. But uh, you know, this kind of follows up too when Ken and I talked about our story about going over to see the girls and putting putting the putting the condom in the we were Ken and I were going through a period where we thought we were gonna die before we ever, you know.
SPEAKER_00It was a period of hope.
SPEAKER_01But yeah, we were we were just like we it was it's a this is a boomer boomer's uh coming of age story where it's like we we hadn't really done anything, you know, in the sex area, so we we wanted to accomplish it. So we read about it, you know. I was like went through the I was between girlfriends or something, and I'm like, you know, I gotta accomplish I gotta accomplish something here. So I went to uh well, he was like the quarterback of the school, you know, and is well known for having a lot of girlfriends and doing a lot of things.
SPEAKER_00Quarterback's got all the chicks, yeah.
SPEAKER_01So I went to our buddy, so I said to him, I says, you know, I kinda need to go on a date, if you know what I'm saying. And has a higher percentage of things happening. And he goes, Oh, I know I I I got just the person for you. So he says, Go look up uh so and so. I'm like, okay. Not a girl, I probably kind of like the pom-pom girls was not in my normal not in my normal circle. Out of the blue, I call her up and like, hey, you know, she's like all excited because again, kind of like what happened when we went over to the pom-pom girls, I was the class president and I was kind of had the clean cut, you know, image, and and so I I go pick her up. She had good hair. I pick her up in my 61 caddy. And I don't know if we've talked about the caddy and some of the other stories, but I had a 61 caddy that you know, I was the class president, I had a 61 caddy, everybody knew who I was. And it's like I pull up and the parents are like, You'd think the president of the United States had pulled up. I'd pull up and I'm like, they're like, whoa, he's here, you know? And I'm like, oh man, I'm feeling like already feeling guilty, you know, like this is not good. I'm not here to get into marriage or anything. And so I said, uh, is uh so-and-so here. I so she's like all excited. I'm you know, I'm feeling I'm meeting the grandma, the mother, the brother, sister, everybody, everybody. And I'm like, oh, this is bad. This was supposed to be kind of more incognito or something. I don't even tell.
SPEAKER_00Are you? I don't even know you're basically describing that you might have had poor intentions.
SPEAKER_01I I was feeling I no wonder I never had any sex because I was feeling guilty all the time. So, so I don't even tell Ray or Ken. No, because that comes in later when I tell them they much later go into hysterics. Decades later. Ray, to this day, Ray won't let me live it down. So anyway, what do I do? Normally you go on a date or something, you go, you know, take them to the pizza shop or whatever. So I'm feeling pretty guilty though, but I I completed my plan. I I went to uh to the drive in, and I can remember it. It was the well you didn't really complete your plan. Well, I you followed step one of your.
SPEAKER_00Did you take her to the restaurant first?
SPEAKER_01No, I went right. It's terrible. We pull in the old drive in there, you know, at the old galaxy. They're not there anymore, doesn't matter. And I'm telling you, the old Cadillac, I just barely turned it off and parked.
SPEAKER_00I don't know. Wait, wasn't the Cadillac quite a roomy vehicle?
SPEAKER_01The caddy had like a couch for a front seat. Like it was everybody loved that car. I turned the car off, and I'm feeling kind of guilty, like right to the drive in from you know, with the family. And all of a sudden, as soon as you turn the key off, key off, she shoots across the front seat. Like, and she's kind of a bigger one.
SPEAKER_00Pretty horned up herself.
SPEAKER_01Horned up, like she and she comes shooting over, and she's like it's like the makeup, like a lot of light layers of makeup, and then they're like going all over my face and smushing me. And and you talk about that lipstick smearing all over me.
SPEAKER_00And then the worst part was You got some of the makeup on the Cadillac interior?
SPEAKER_01No, I was mostly on my face for right now. Okay, and I was getting worried about that bad. Okay, not that I was getting I was getting worried about that, but now the hair has got uh like like Aqua Net in it. Oh, that's it. Like that hair spray, yeah, and my eyes are like like watering, I'm like watering, and I can't see, and I got smushy stuff all over my face. And I'm like, I can't do this. I can't, this is this is bad. Maybe you were just feeling guilty. I got some kind of standard, you know. It was like an animal. It's like it's I don't care how horny I am. I'm maybe I'm gonna be a homo. I don't know. I got like a little guy on my shoulder, like an animal house going. I'm exactly. I'm like, I'm like, this is bad, but I think I'm gonna not do this.
SPEAKER_00Wait, one guy on the shoulder is telling you to go for it. Yes, and the other guy's doing what?
SPEAKER_01Saying I'm a homo.
SPEAKER_00So I got AquaNet in my eyes. So essentially you were conflicted at this point.
SPEAKER_01No, you know, I was AquaNet. I was like, I can't do this. I can't for what I don't like, I don't like layers of makeup and dancing of the hair. Was it it was probably real treatment?
SPEAKER_00Maybe you were so overwhelmed, maybe you weren't thinking straight.
SPEAKER_01I don't know. I turned it down. I'm like, I pushed away, and I'm like, you know what? It was just and so I like made some stupid excuse up like an idiot. Like, you know what? Like you had cramps when your grandma came over. I gotta go home. I gotta go home. Like he had to go to the National National Honor Society. I didn't even wait to see the rest of the movie because I decided I was done. Done. I can understand that though. So then it was funny. I kept it a secret, and then I made the mistake of telling Ken and Ray. Oh, Ray, I didn't make a big deal. Ray was laughing his guts out. He thought it was so funny. So similar to Randy's, you know, Randy, you know, he turned that down. Yeah, right. I had to. So but he was only 14. There was no I I was like 60. Wow. I still have PST. What do they call it? PST. PTSD. When I see Gaquinet. Yeah.
SPEAKER_00All right. Well, you guys, uh, thanks for listening. Maybe you can relate to some of those experiences yourself. Hopefully, you'll listen in next time. Thanks. See you bye.
SPEAKER_01Hey, thanks for joining us here on Boomers on the Edge. We hope you'll join us again. And until then, have a great time. Thank you.