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. 1H AGO

    Dating Etiquette (Boomers on the Edge Style)

    Guest host Randy, a single Boomer navigating the modern dating world, shares how the Buds—have a knack for unintentionally sabotaging his romantic evenings. Randy has one firm rule on dates: no phone ringer. He keeps things polite and distraction-free, with only the vibration setting on—just in case one of his adult kids needs him in an emergency. But one night at dinner, his phone won’t stop buzzing. It’s Kenn. Randy ignores it at first… then again… and again. Finally, trying to save face, he excuses himself and tells his date that, given his medical background, the call might be urgent—possibly someone needing expert guidance during a procedure. Sounds impressive—until he answers. On the other end, Kenn casually explains that he and Ray are out deer hunting and need Randy to walk them through field dressing their “patient.” At that moment, the illusion shatters. The “emergency” isn’t exactly what Randy’s date had in mind—and it quickly becomes clear this is not a human medical situation. Needless to say, the date doesn’t quite recover. Another well-intentioned (but perfectly timed) interruption from the Buds—and another unforgettable dating disaster. Classic Boomers on the Edge: equal parts outrageous and hilarious. Boomer rating: Under the EdgeSend us Fan Mail https://www.boomersontheedge.com boomers@boomersontheedge.com

    5 min

  2. MAY 18

    You Roared?

    In the 1990s, as Boomers settled into parenthood, everyday life came with its fair share of chaos—and comedy. In this episode, Kenn shares a story that perfectly captures both. After noticing a neighborhood kid picking on his son, Kenn pulls him aside and gives some blunt, old-school advice: if the bully doesn’t stop, he has permission to punch him in the nose. Not exactly textbook parenting—but very on brand. A few days later, while chatting with a group of moms as the kids play nearby, Kenn spots the same bully causing trouble again—this time smacking kids with a piece of rubber tubing. Suddenly, a loud scream cuts through the air. The bully is crying. Kenn rushes over, expecting the worst, and asks his son what happened. His son, looking a bit sheepish, simply says: “I roared.” Confused at first, Kenn quickly realizes—his son didn’t throw a punch. He scared the bully off by roaring like a lion. Seizing the moment, Kenn rallies all the kids to roar together, turning it into a lesson: you don’t always have to fight back—you can stand your ground in other ways. Meanwhile, he can’t help but enjoy watching the bully get a taste of his own medicine. Just another unconventional—and unforgettable—parenting moment from Boomers on the Edge. Boomer rating: Under the Edge.Send us Fan Mail https://www.boomersontheedge.com boomers@boomersontheedge.com

    6 min

  3. MAY 11

    Hair Removal and Hot Ointments

    Kenn and Ron take things back to the 1970s with another round of unforgettable high school track stories—this time featuring a mix of pranks, poor decisions, and plenty of laughs. The first tale centers on a classic locker room prank: someone secretly slipped hair-removal cream into a teammate’s varsity jacket sleeves. The result? One very confused (and suddenly very smooth-armed) athlete. To this day, the culprit remains a mystery. The second story shifts to a dedicated—but slightly over-the-top—long-distance runner who swore by using extra-strength warming ointments to battle the cold. Despite constant warnings from teammates to go easy, he didn’t hold back. During one two-mile race, things took a painful turn when the ointment made its way into his eyes. What followed was a chaotic attempt to finish the race while half-blinded, yelling, and tearing up—earning more laughs than sympathy from the sidelines. From harmless pranks to questionable race-day decisions, these stories capture the wild, anything-goes spirit of 1970s high school sports. Another nostalgic—and hilarious—installment from Boomers on the Edge. Boomers rating: Under the Edge.Send us Fan Mail https://www.boomersontheedge.com boomers@boomersontheedge.com

    7 min

  4. MAY 4

    The Secretary Said What!

    Guest host Randy is back with the crew, bringing along a classic (and slightly cringe-worthy) workplace story from the 1980s. While managing a team project, Randy arranged for a vendor to host a lunch and present their product. During an internal meeting, he asked his secretary to let him know when the sales rep arrived. Not long after, she burst into the room in a panic, gesturing urgently. The issue? The sales representative had arrived—but the secretary was so thrown off by her being a little person that she awkwardly announced it in a way that stopped the room cold. Unimpressed with the dramatics, Randy told her to send the guest in. The sales rep turned out to be a confident, personable professional—about four feet tall—who quickly put everyone at ease and invited the team out to lunch. Things got even more memorable on the ride over. One of Randy’s team members offered to drive her in his pickup truck, but she needed a stack of phone books to see over the dashboard. Midway through the trip, a sharp turn sent her sliding off the stack and briefly disappearing under the dash—much to the shock (and later amusement) of the team following behind. Without missing a beat, the driver helped her back up, and they continued on. By the time they reached the restaurant, everyone—including the sales rep—was laughing. Her professionalism and good humor left a lasting impression, and Randy’s team ultimately chose her product for their project. It’s a funny, eye-opening snapshot of a different era—highlighting how workplace attitudes and social awareness have evolved over time. A classic “Boomers on the Edge” throwback. Boomer rating: Under the Edge.Send us Fan Mail https://www.boomersontheedge.com boomers@boomersontheedge.com

    8 min

  5. APR 27

    Wedding Memories

    Weddings are unforgettable milestones—no matter the decade, they come with their fair share of chaos, comedy, and stories that only get better with time. In this episode, the buds take a nostalgic trip back to the 1960s and 1980s, sharing some truly over-the-top moments that perfectly capture the spirit of wedding day mayhem. Ron kicks things off with fond memories of the music at weddings he attended as a kid. Back then, polka bands ruled the scene—but young Ron had other ideas. Whenever he requested a rock song, the band would reluctantly attempt classics like “Spinning Wheel” or “Proud Mary.” The results? Polka-fied versions that left much to be desired. Ron quickly decided they were better off sticking to what they knew best. Kenn brings the drama with a wedding day disaster he’s never forgotten. The centerpiece of his reception was supposed to be a stunning, multi-tiered cake complete with pillars and cascading details. But as the evening dragged on, there was no sign of the baker—or the cake. When the baker finally arrived, it wasn’t the grand masterpiece they’d ordered. Instead, it was a mangled mess. Apparently, there had been an accident en route, and the cake didn’t survive the journey intact. Despite the condition of the cake, the baker still expected full payment. Kenn refused—but his bride, determined not to let the situation overshadow their big day, urged him to let it go and pay. Weeks later, Kenn considered taking legal action, but once again, his wife chose preserving the memory over prolonging the drama. To this day, Kenn admits he still wishes he had followed through. Once again, the Boomers deliver a perfect blend of humor and heartfelt storytelling—proving that sometimes the most memorable wedding moments are the ones that don’t go according to plan. Boomer rating: Under the Edge.  Send us Fan Mail https://www.boomersontheedge.com boomers@boomersontheedge.com

    11 min

  6. APR 20

    Surprising Your Parents - Inconvenient Accidents

    Back in the 1970s, kids spent their days outside—running wild, getting into trouble, and occasionally turning an ordinary afternoon into an unexpected trip to the emergency room. In this episode, guest host Randy joins Ron to share a couple of unforgettable stories that both end the same way: with their dad asking, “How did that happen?!” Randy kicks things off with a tale of youthful determination gone wrong. At 13, he and his friend Jonny set out to retrieve a tennis ball that had landed on a school roof. What started as a simple mission quickly escalated into climbing, sneaking into a courtyard, setting off an alarm—and ultimately, Randy breaking his arm. Determined not to ruin his parents’ wedding anniversary, he keeps it quiet… until midnight, when the swelling becomes impossible to ignore. One knock on the bedroom door later, the celebration is officially over, and the family is headed out for a late-night ER visit. Ron follows with a story from his own teenage years. Left home while his dad grabs pizza, Ron, Randy, and Kenn decide it’s a great time to start jumping a large bush in the front yard. Ron clears it—but lands badly on decorative bricks, severely spraining his ankle. When their dad returns, the boys try to play it cool, but as the pizza disappears, Ron’s ankle grows to an alarming size. The verdict? Another “I think I broke it” moment—and another unexpected trip to the emergency room. But in true Boomers on the Edge fashion, the story doesn’t end there. On the ride home, Ron—lying in the backseat and convinced he’s hallucinating—watches bright, swirling lights fill the sky. Turns out, he’s witnessing a rare sight over Detroit: The Northern Lights. Another classic episode filled with mischief, memories, and the kind of stories that only seem to happen when Boomers were being Boomers. Adult themes.Boomer rating: On the Edge.  Send us Fan Mail https://www.boomersontheedge.com boomers@boomersontheedge.com

    13 min

  7. APR 13

    The Mutiny Bar

    Ron takes us back to the wild 1980s with another unforgettable business trip story. While traveling for training on the East Coast, Ron’s buddy Tom had a habit of hitting late-night discos and pretending he was single—despite being very married. His ego just needed a little reassurance now and then. On one trip, Tom insisted they drive over 90 miles to revisit a place called the “Mutiny,” convinced it would be just like the “ladies’ night” they’d experienced a couple months earlier—full of energy and attractive women. But the moment they walked in, something felt off. A rude waitress. Wall-to-wall guys. Not a single woman in sight. And one lone dancer putting on a very… expressive performance to disco music. As the night went on, the bar filled with hundreds of men—and still no women. At 10:00 PM, the band kicks in—and suddenly seven pint-sized Elvis impersonators in sequins strut out in a full-on conga line. Then it hits them: a glowing red teleprompter spells it out— “Alternative Lifestyle Night.”  Tom’s over-the-top negative reaction was priceless. Ron, on the other hand, could barely breathe from laughing—especially knowing Tom had insisted on driving 90 miles for the experience. A perfect case of being in the wrong place at the wrong time… and another classic Boomers on the Edge story. Adult themes and language.Boomers rating: Over the Edge.Send us Fan Mail https://www.boomersontheedge.com boomers@boomersontheedge.com

    14 min

  8. APR 6

    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
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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
    37
  • Rating
    Explicit
  • Copyright
    © 2026 Boomers on the Edge
  • Show Website
    Boomers on the Edge

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