15 People Share the Cringiest Midlife Crisis They’ve Ever Seen Someone Go Through
People on Reddit traded stories about the most painfully awkward midlife crises they had witnessed, and the results would give anyone second hand embarrassment. Seeing someone throw it all away for a moment of excitement is a sad, yet strangely comforting type of thing. Since we’re not doing that, right?
What most of these people went through were dramatic transformations that left everyone around them wondering what had happened. Here are memorable stories shared in the discussion, ranging from questionable fashion choices to decisions that made families or workplaces cringe.
The Garage Guru
An uncle quit his stable corporate job, spent his savings on crypto, and launched a “mindset and finance” podcast from his garage. He had 12 listeners but talked and dressed like Patrick Bateman, making the whole transformation especially awkward.
The Trench Coat Phase
A dad hit his mid-40s and decided he was tired of people “pushing him around.” He shaved his head, grew a goatee, and started wearing trench coats. His family did not exactly embrace the transformation.
A Very Unexpected Hobby
One person’s dad went through a midlife transformation so unusual that even his child wasn’t sure whether to call it cringe anymore: he became a furry, leaving the family to adjust to an unexpected new identity.
The Skateboard Incident
One man decided to build a skateboard and start skating waxed curbs, attempting slides despite apparently being well past the usual age for such experimentation. Then he broke his wrist, and his wife promptly took the skateboard away.
The Apocalypse Prepper
A previously fun-loving, laid-back dad became an extreme evangelical redneck in his mid-40s. He obsessed over Satanism, women’s rights, health, taxes, and Gen Z, while stocking ammunition and canned food for an imagined communist takeover.
The Alpha Male Makeover
A coworker in his late 40s left his wife of 20 years, bought a bright red sports car, dated a 22-year-old barista, and got a huge tribal sleeve tattoo. Then came daily motivational “alpha male” reels.
Buying Twitter For Attention
One man supposedly bought Twitter for the simple purpose of making everyone on the platform see his tweets. The sheer absurdity of the explanation makes the story work as a joke about Elon Musk’s famously attention-grabbing acquisition.
The Gen Z Biker
A man in his late 40s bought a loud motorcycle, started wearing leather vests everywhere, and suddenly tried using Gen Z slang around his children’s teenage friends. The resulting secondhand embarrassment was reportedly off the charts.
Trading Families For Youth
One observer said they cringe when someone abandons a middle-aged spouse and teenage children for a much younger partner and babies. The ego boost might feel good initially, but the stress and family consequences can last much longer.
The University Party Circuit
A married man in his 40s enrolled in a part-time master’s program, then joined the university skydiving club despite never having skydived. He eventually dropped the degree but stayed in the club, partying with younger students almost nightly.
Grandpa’s Erotic Literature
After his wife died, one grandfather wrote and self-published a book of erotic stories, then handed signed copies to relatives. When he told his son it might spice things up in the bedroom, the resulting family-wide cringe was unforgettable.
Money Going To Young Women
A father with a small but relatively successful business reportedly began draining the company’s money to give it to young women. The story is remarkably blunt: his business was functioning, but his priorities during the crisis were anything but.
The Ayahuasca Detour
The mother of an old high-school friend began dating her son’s 18-year-old friend, allegedly grooming and supplying drugs to young men. She became obsessed with ayahuasca, eventually living as a shaman in South America before returning during the pandemic.
The MMA Fantasy
A man in his mid-40s joined an MMA club, got tattoos of MMA quotes within a month, and pushed for a fight despite limited ability. After six months, he competed, panicked after the first punch, and never returned.
The Five-Year Backfire
A friend of a friend left his wife and two children, pursued younger women, got his hair and teeth done in Turkey, bought clothes, a convertible. Five years later, he was single, living in a rental with a car.