A 1960s Holiday Adventure

In this festive, retro-themed episode, Craig, Kenn, Ron, and guest host Randy swap stories about holiday shopping in the 1960s. Ron and his younger brother Randy revisit one of their family’s most legendary tales—five-year-old Randy’s epic struggle to make quick decisions, thanks to his intensely analytical mind, and the surprising consequences that followed.

During a long day of shopping, their parents try motivating the kids—Ron (8), Randy (5), and Sandy (3)—with the promise of a toy at the end of the trip. While Ron and Sandy eagerly snatch up their prizes, Randy’s endless deliberation tests everyone’s patience, ultimately costing him his toy and earning him an unforgettable lesson.

Ron and Randy share several hilarious moments from childhood that highlight a young Randy’s analytical (and often comically slow) approach to decision-making.

Join us for a nostalgic, laugh-filled journey back to the days of childhood, family shopping trips, and holiday memories!

• Boomer rating: Under the Edge.

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Guest host Keith joins the show to help recount one of the most legendary Boomers on the Edge stories—the night at the Duchess.

It’s late, they’re underage, and the Buds (John, Keith, Ray, Kenn, Craig, and Ron) have wandered into the Duchess, a notoriously grimy Detroit strip bar. It’s Kenn’s very first time in a place like this… and his reaction does not disappoint.

While most of the Buds rush to claim their spots around the stage, Kenn and Ron hover awkwardly near the entrance, trying to process the scene. Before long, Kenn starts whispering to Ron that the bar is “scummy”—a whisper that quickly escalates into his unmistakable “passion voice.” Within moments, he’s shouting across the bar, “They’re all scum!”

Ron panics, patrons turn, and the bouncer decides he’s seen enough. With a looming brawl on the horizon, he boots the entire group out in one sweep. And just like that, the Buds’ night is over.

This episode is pure comedy from start to finish—a true Boomers on the Edge classic. Buckle up—it’s a riot from start to finish.

• Adult themes and language.
• Boomer rating: On the Edge.

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In this laugh‑out‑loud episode, Craig shares a wild workplace story about a young apprentice who couldn’t stop bragging about his wife’s beauty—complete with revealing photos. The apprentice proudly flashes a picture, declaring, “This may or may not be my wife.”

That’s when Craig hatches a prank: each day, he shows the apprentice increasingly risqué photos of “his own wife”—images secretly pulled from the internet. The game quickly escalates into a hilarious competition of one‑upmanship, with both sides trying to outdo each other in the battle of “may or may not be their wife’s” pictures.

Tune in for this outrageous tale of workplace mischief, playful rivalry, and comedic escalation. It’s bold, funny, and guaranteed to entertain!

• Adult themes and language.
• Boomer rating: Way over the Edge.

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