Boomers on the Edge

Boomers on the Edge
  • 5.0 (21)
  • IMPROV
  • UPDATED WEEKLY

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.

  1. 6D AGO

    The Drive-In Date

    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 EdgeSend us Fan Mail https://www.boomersontheedge.com boomers@boomersontheedge.com

    8 min

  2. MAR 30

    Crotch Stories

    In this episode of Boomers on the Edge, Kenn and Ron dive headfirst into one of the most awkward—and hilarious—subjects known to mankind: the crotch. Because let’s face it… some of the funniest disasters in life seem to happen right there. Ron kicks things off with the story of a poor guy who drops a hot cup of coffee straight into his lap and immediately performs what can only be described as the “scalded crotch shuffle” across the room. It’s the kind of dance nobody wants to do—but everyone in the room remembers forever. He also flashes back to the 1980s, when a senior salesperson tries to help a young Ron impress a customer by proudly telling them he’d love to help with their “jewels.” Of course, he meant their most valuable projects… but the customer wasn’t entirely convinced and looked like he might bolt before anyone got too close. Kenn piles on with the story of a coworker whose well-meaning mother washed his underwear along with some fiberglass-lined drapes. The result? A full day of mystery itching, panic, and a man who could not stop grabbing his crotch while trying to figure out what the heck was happening. The buds once again prove that the 1980s workplace was a goldmine of ridiculous, unscripted comedy—especially when things went terribly wrong below the belt. Another unapologetically funny episode from Boomers on the Edge. Adult humor.Boomer's rating: On the Edge.Send us Fan Mail https://www.boomersontheedge.com boomers@boomersontheedge.com

    11 min

  3. MAR 23

    Crying Wolf and ATV Riding

    Kenn and Ron look back at the 1980s and the early days of ATV riding—when exploring the woods meant real risk and there were no cell phones to call for help if something went wrong. Ron tells a story about riding Honda ATC 90 three-wheelers with his dad in the woods of northern Michigan. Their ride takes a dangerous turn when a truck and trailer cut them off on a narrow forest trail, forcing his dad off the road and down a steep embankment in a violent crash. There’s just one complication: Ron’s dad had a long-standing reputation for dramatic reactions to even minor bumps and bruises. In the family, it was almost routine to assume he was exaggerating whenever he claimed he was hurt—much like the classic boy who cried wolf. After the crash, his dad insists he can’t move, so Ron calls for emergency help and gets him taken to the hospital. Surprisingly, doctors send him home with a clean bill of health and no broken bones, reinforcing the family’s belief that he might be playing things up again. The next day, during a trip to Ann Arbor, his dad rides in the back seat surrounded by pillows, groaning about every bump in the road—prompting Ron and his mom to quietly laugh themselves into hysterics. But the joke is on them. A second hospital visit reveals the truth: he actually had a broken sternum. The moral of the story? Don’t cry wolf… because when something really is wrong, people might not believe you.  Another classic Boomers on the Edge tale.  Adult humor.Boomer rating: Under the Edge.Send us Fan Mail https://www.boomersontheedge.com boomers@boomersontheedge.com

    15 min

  4. MAR 16

    Sibling Antics 2

    The adventures continue as guest host Randy joins Kenn and Ron for another round of outrageous childhood stories straight from the 1960s. Kenn kicks things off with a family “game” their mom introduced—one that put their love of snacks to the test. Forget competitive eating contests… the Coney Island hot dog challenge has nothing on a living room showdown involving an impressive number of cheese puffs crammed into eager mouths. It was messy, competitive, and absolutely unforgettable. Following up on the fan-favorite Sibling Nighttime Antics episode, Randy shares his side of the story about Ron’s so-called “character-building” techniques. Ron insists his big-brother tactics were simply preparation for the real world. Randy might describe it differently. Ah yes… 1960s brotherly love at its finest. From learning grocery store jingles (accompanied by “motivational” taps) to mastering the art of dodging surprise pillow attacks from above, these stories capture the wild, unsupervised, and hilariously chaotic world of growing up with siblings in the ’60s. You either learned fast—or got flattened. Another nutty, laugh-out-loud episode from Boomers on the Edge! Boomers rating: Under the Edge.Send us Fan Mail https://www.boomersontheedge.com boomers@boomersontheedge.com

    18 min

  5. MAR 9

    Sibling Nighttime Antics

    It’s another hilarious flashback to the 1960s, when the Buds were just little kids and bedtime was strictly 8:00 PM — whether they were tired or not. Of course, sleep was the last thing on their minds. Causing chaos? That was a different story. Ron kicks things off with a mischievous memory of convincing his much younger brother to go on a “top secret” mission. While their parents entertained guests, Ron saw an opportunity: maybe a snack raid on the kitchen. But his true plan? Outfit his unsuspecting little brother with a sheet for “camouflage” and send him straight into trouble. What happens next is pure sibling strategy — and classic 1960s consequences. Kenn follows with a tale from a darker place — literally. He and his twin brother dreaded bedtime, thanks to their former Marine dad’s firm rule: door shut tight, lights completely off. The twins’ nightly mission became cracking the door open just enough to let in a sliver of light. Let’s just say Dad was not amused… and discipline was swift. Both stories end the way many 1960s childhood escapades did — with one sibling taking the fall while the other hid quietly, relieved it wasn’t them this time. Relive the laughter, the mischief, and the unmistakable parenting style of another era. Boomers on the Edge once again takes you on a nostalgic ride down memory lane. Boomer rating: Under the Edge.Send us Fan Mail https://www.boomersontheedge.com boomers@boomersontheedge.com

    13 min

  6. MAR 2

    Workplace Tales

    In this episode, Kenn and Ron swap outrageous workplace stories that prove no office day is ever truly “normal.” Ron opens with a corporate curveball from his early management days. When new technology wipes out the company’s all‑female Message Center, he’s tasked with finding new roles for the displaced team. He thinks he’s got it handled—until his buddy Joe suddenly fills Ron’s open position with a stunning, mysterious secretary shipped in from across the country. Ron is left holding the bag, forced to deliver bad news to one of the loyal Message Center women… and wondering what exactly Joe is up to. Then things get strange. Their new co‑worker’s behavior becomes increasingly odd, office drama starts piling up, and suspicions swirl. And just when the Buds think they’ve seen it all, she vanishes without warning. The truth eventually surfaces in spectacular fashion: she’s been moonlighting as an exotic dancer. Not to be outdone, Kenn adds his own unforgettable “Dress for Success” disaster—a day at the office spent unknowingly sporting a panty shield stuck to his elbow… and possibly other places. From management misfires to wardrobe malfunctions, this episode proves once again that the Buds’ careers were anything but boring. Another unbelievable episode from the “Buds” on Boomers on the Edge. Adult humor.Boomer rating: On the Edge.Send us Fan Mail https://www.boomersontheedge.com boomers@boomersontheedge.com

    15 min

  7. FEB 23

    Wingman

    Guest host Randy is back with another unforgettable tale from the 1970s. As young teenagers, Randy and his buddy Johnny hatch a bold plan: a double-blind date while Johnny’s parents are away for the night. With the house to themselves, the boys “borrow” a little liquid courage from Johnny’s dad’s liquor cabinet and pass the time engaging in some classic ’70s teenage mischief—perched on the roof, laughing, and making questionable decisions. Soon, the girls arrive on their bikes: one a well-known school beauty, the other a star athlete… and significantly taller than either Randy or Johnny. That’s when Johnny drops the bomb—Randy’s date for the night is the athlete, who stands a solid six inches taller than the boys. In true teenage wingman fashion, Johnny promptly disappears into the next bedroom, cranks up the music, and locks the door—leaving Randy to fend for himself. What happens next is an awkward, chaotic, and painfully funny encounter that ends with a split lip and a story that has become a true Boomers on the Edge classic. Adult humor.Boomer rating: On the Edge.Send us Fan Mail https://www.boomersontheedge.com boomers@boomersontheedge.com

    12 min

  8. FEB 16

    Healthcare Antics

    As Kenn, Craig, and Ron officially cross into “senior citizen” territory, one thing becomes clear: the doctor’s office is starting to feel like a second home. But in true Boomers on the Edge fashion, the “Buds” can’t seem to have a normal medical visit without it turning into comedy gold. Kenn kicks things off with an orthodontics office disaster. Thinking the kid in the chair in front of him was his son, he starts clowning around—making goofy noises, cracking jokes, even pretending to dump Tic Tacs into the poor kid’s mouth—only to be stopped cold by a horrified mom. Turns out… wrong kid. His son was one chair over. Instant legend status at the orthodontist. Ron shares his colonoscopy follow-up, where his doctor casually mentions the chart says he has a “sensitive colon.” Ron, stunned, asks how they could possibly know that just by looking. The answer? He told them… apparently during that so-called “twilight” sedation. So much for privacy. And Kenn wraps it up with another questionable life choice: passing the time in exam rooms by rummaging through the doctor’s cabinets—until a nurse catches him red-handed. Craig and Ron react exactly how you’d expect: equal parts shock, disbelief, and “Why would you do that?!” It’s another round of ridiculous, relatable, and slightly chaotic stories as the Buds navigate the wild world of modern healthcare—Boomer style. Funny, awkward, and a little bit nut's… just another day on Boomers on the Edge.  Adult humor.Boomer rating: Under the Edge.Send us Fan Mail https://www.boomersontheedge.com boomers@boomersontheedge.com

    20 min
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5
out of 5
21 Ratings

About

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.

Information

  • Creator
    Boomers on the Edge
  • Years Active
    2025 - 2026
  • Episodes
    30
  • Rating
    Explicit
  • Copyright
    © 2026 Boomers on the Edge
  • Show Website
    Boomers on the Edge

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