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Apparently millennials are turning to midlife-crisis hobbies (phew, it’s not just me, then). But if you thought that meant the usual midlife-crisis stereotypes, think again. Our version looks less like rebellion and more like a wellness retreat: taking up running or pickleball, becoming self-appointed sourdough or gardening experts, and getting really into ice baths and saunas.
But that’s all far too tame for our list today. Someone asked Reddit about the cringiest midlife crisis they’d ever witnessed, and users delivered. Some are exactly what you’d expect—drastic career changes, bright-red sports cars, and younger lovers. Others might be harder to see coming, including someone who apparently went full furry. And while it’s mostly hilarious, a few entries might even double as cautionary tales. Because sometimes what you think is a glow-up is actually a blow-up—and a spectacularly cringe one at that.
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#1
I knew a guy who built his skateboard and went out to skate a waxed curb doing slides and stuff. Then he broke his wrist and my wife took my skateboard away 😭.
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#2
My dad in his mid 40s (early 2000s) went from fun-loving laid back comic to extreme evangelical redneck. He started sucking up all the energy in the room. Satanism, women's rights/health, taxes, gen Z are out to get him. He stocks ammunition and canned food for when communism takes over.
I miss my old dad.
Goober.Smoocher 9 hours ago
That’s incredibly sad because OP knew him as a real person, not a brainwashed zealot… but that’s all that’s left now.
#3
Mine. Wife and I bought an open top sports car and toured the country in our early 30ies. Then came kids and the car has been mostly sitting in a garage, driven once a year for service/technical - we don't want to sell it for emotional reasons and it's actually gaining value as of lately. We're in our late 40ies now.
Then comes an unfortunate event last month where we lost the family car and the replacement isn't coming for another month.
So our daughter gets shuffled to activities with the open top sports car. When my wife does it, it is cool. When I do it, I park away from the destination to avoid anyone seeing us as it's super embarrassing. .
#4
A friend of a friend went full on midlife crisis, left his wife & 2 children because of all the other women he could get, went to Turkey to get the hair & teeth done, makeover done in Brown Thomas to get a whole new waredrobe, bought a convertable AND a motorcycle.
Fast forward 5 years he is single, living in a rental 2 bedroom place with a broken down car trying to make the 5 year old clothes last. His wife however is living her best life, best thing that ever happened to her she reckons, her career has taken off and having agreed week on week off custody of the children means she has a lot more time on her hands than she ever had before.
#5
45 yr old man with ALS paralysis cheated and left his long time loving and fun wife for his home health aide. Aide got bored after 6 months and left him. Now he is on his own, living in a facility. Ex-wife met someone new and is getting re-married.
#6
My coworker in his late 40s dumped his wife of 20 years, bought a bright red sports car, started dating a 22‑year‑old barista, and got a huge tribal sleeve tattoo. He also began posting cringey motivational “alpha male” reels every single day. The whole office watched it unfold.
#7
Divorce, younger girlfriend, bought a 1200cc sports motorbike. All the standard things.
The real cringe though was that he got the house in the Divorce, *and decided to put down bright red carpet in every single room* because his wife wouldn't let him have red carpet in their bedroom.
Ive never seen anything like it.
#8
The worst ones for me are the people who seemingly can’t handle their advancing age and seek to join in with younger groups to try act like they’re younger. See especially - guys who leave their wives/children for women much younger than them, and suddenly they have babies to support when they’re in their 50s. I always feel bad for the kids left behind/created like this, only to be neglected by their father’s ego.
Have witnessed it personally a few times myself, including a guy - now in his 80s! - who is trying to get something going again with much younger women! Go see a therapist dude, for real. Better than starting a THIRD family, surely.
#9
My uncle quit his accounting job at 49 and bought a beat-up van to 'travel and paint'. He made these weird YouTube videos of himself strumming a guitar badly in national parks while narrating about finding his 'inner truth'. The family still gets tagged in the comments.
#10
My dad left my mom pretty recently (25 year marriage) and got an apartment in the middle of nowhere, a motorcycle, and now texts me every week that he invested in crypto or is getting a back tattoo. He still texts my mom all the time though.
Definitely a midlife crisis.
#11
A guy in his late 40s bought a loud motorcycle, started wearing leather vests everywhere, and suddenly tried talking in Gen Z slang to his kids' teenage friends. Secondhand embarrassment was off the charts.
#12
Leaving his second wife (who was an au pair for the first wife’s children) for the au pair.
His third wife did not get an au pair for their kids.
#13
Very recently, father of my one of my nephew's friends, his kids are 10 and 6, decides that being a suburban dad isn't what he wants, leaves wife, moves into an apartment over a wine shop, sells his SUV, buys a Mustang, gets on the apps trying to date younger women, quit his white collar job to get and be a lifestyle influencer. Now, he stands alone at school pickup because he can't understand why the other parents dont want to associate with him. He's also upset with ex-wife because she's pursuing child support based on the income he voluntarily abandoned, and it's screwing up his new plans.
#14
I have two friends that quit stable jobs to become full time Disney influencers in their 40’s. And they barely have any followers but they keep pushing out content trying to make something happen.
#15
Guy I used to work with enrolled in a part time masters degree course, where he mainly did night classes, so far so good. He then joined the University's skydiving club, he'd never skydived in his life, mainly so he could go out drinking with the younger students and try and get with the 18 year old girls. Then he dropped out of his Masters course, stayed in the skydiving club, and was out almost every night with students. He was in his 40's and married with 2 kids!
#16
My Dad started cheating on my Mum, found a new 20 something old girlfriend and spent all his money on her. Bought her a jaguar, plastic surgery, a cafe to name a few. Started committing fraud to pay for all of the things, went to prison for 3 years.
#17
My dad had a phase when I was in high school (so peak teenage angst) where he decided he was sick of people “pushing him around” so he shaved his head, grew a goatee and started wearing trench coats. It was not well received hahah.
#18
Probably my own. I spent a good 100k on collectibles. Pop culture stuff.
Tons of prints too.
No idea why I did that.
Been selling it off slowly for a while now.
#19
My ex wife, wife at the time, have a lesbian affair with our female babysitter 14 years her junior.
#20
My uncle who left his stable corporate job, spent his savings on crypto, and started a "mindset and finance" podcast in his garage. He has 12 listeners, but he talks and dresses like he’s Patrick Bateman.
#21
I'm a mma coach and had a lad mid 40 join the club which happens a lot tbf but most of them just want to train and not try and compete at a high level. This lad other than having a bit of muscle wasn't at all athletic. Got tattoos of our club and mma quotes within the first month kept pushing me to get him a fight even though he had learned basically nothing. Caved in after 6 months just to shut him up, he made 100s of posts on social media coming up to fight invited everyone he ever met. Day of the fight comes he's absolutely scared as he maybe sparred a handful of times despite me trying to sort him out with more . First punch that connected with him in the fight he absolutely broke down kept turning his back on who he was fighting and the ref called it off after a minute my 7 year old niece would of done better. Never seen him in the club again after. Still has the profile of the square off of the fight seconds before he got an absolute kicking in front of everyone he knows though.
Upstaged75 7 hours ago (edited)
This sounds like that episode of friends when Monica was dating the rich guy who decided to become an ultimate fighter. And got his a.ss kicked so badly in the first 2 minutes he nearly died. 😂
#22
Bankers in their late 40s, buying 16k Pinarello Dogmas (think a Ferrari for bicycles), Tour de France level equipment and accessories, expensive superfood gels only to ride 20km to a café where they act like they're decorated athletes. Very tough to watch.
Edit: People seem to think I'm pointing out the optics of it or suggesting that it's funny in some way to ride a bike - this is of course not the point. I've been cycling for 25+ years and you can ask everyone who is / was serious about the hobby, how they feel about how it changed in the last years... The sport is not as welcoming, it's now snobby, douchier and the crowd it attracts is not about achieving an athletic goal, but more and more about pointless consumerism.
Ace 4 hours ago
Cycling has always attracted this sort of person, nothing that has changed in 25 years or longer. Even when I was a teenager I knew a whole bunch of people in a local cycle race club and there was always the one rich kid with the latest greatest kit who couldn't ride for toffee.
#23
My sister's friend was married with 2 teenagers and had a successful and wealthy husband. They lived a very comfy life.
Then he knocked up their much younger nanny AND knocked up another woman at the same time.
Needless to say, they are now divorced and he is raising a baby with one of the other women.
#24
Friend of ours.
1. Broke up with his wife.
2. Started going to the gym.
3. Stopped going to the gym.
4. Keeps Talking about Gym lifestyle and health
5. Keeps asking how I dated so much in my 20s
6. comments Creepy S**t on every attractive women from gym, when they post stuff
7. doesnt understand that he is a fat, balding guy in his 40s who will never ever be a „ladies man“ and that there is nothing wrong with tinder.
Its him. .
#25
All these stories about men having a midlife crisis, but what about women? I caught my mom having an affair with some guy who owned a bunch of car repair places. She used some inheritance money from an aunt to buy a BMW convertible, moved out, and got an apartment on the water.
Meanwhile, my dad started drinking heavily and partying with younger dudes he met through the gym, but the entire time he still wanted her back.
After about two years, she finally moved back. Coincidentally, this was right around the time my dad was talking to a lawyer and was about to cut off the monthly money he’d still been giving her.
They got back together and somehow just carried on like none of it ever happened. That was 15 years ago, and they’re still together. 😂.
#26
My FIL dyed his fully gray hair and eyebrows blonde in an effort to look younger (I believe that’s the reason, he never admitted that was the reason but his wife is nearly 10 years younger than him and their youngest child was 20 at the time with friends asking if my FIL was his grandpa). Not cringe on its own, though he neglected to either dye or shave his mustache so he had cherubic golden curls on top, Einstein stache on the bottom. We weren’t allowed to say anything lol. Love the guy though.
Chich the witch 7 hours ago
New a guy in his 60s. Split from his first wife. Had jet black hair and a late 30s new wife. Hair didn't look quite right and later found out he used shoe polish.
#27
A guy who never went to college, but ended up being quite successful and basically retired at 40, decided he wanted to go to college. He wanted the full college experience, so he moved into the dorm.
That really creeped out a bunch of parents, having a 40-year-old man living with their 18-year-old sons and daughters, since it was a co-ed dorm.
Ace 4 hours ago
It's not entirely clear to me what they mean by a 'dorm' but I'm imagining that its not just a row of beds in a big room and that each person actually has their own private sleeping space. SO although it may be a little weird of him to want to do this, I don't see why his age should make any difference to the other students.
#28
My neighbour buying a cyber truck and a diamond crusted Rolex all in the same week….
Multa Nocte (she/her 8647) 7 hours ago
I will honestly never understand someone buying one of these.
#29
The typical red sports car, a woman on the side, his wife left him, eventually the young woman did too. The last time I saw him he was sitting in a pub on his own eating some sad pub grub, he had aged years,he said “ I miss my wife and I miss her cooking “.
#30
Divorced his wife and the mother of his kids after 30+ years. Married a Vietnamese, took out a huge loan and brought a muscle car. Closed the car door on his fingers and then had a full blown heart attack.
#31
I don’t even really know if I consider it cringe anymore but my dad turned into a furry
Edit: See I love telling random people this because this is always the reaction lmao, no i’m not going to elaborate but his ‘furtype’ is a badger. He also has his own band with fellow furries. Ok that’s all your getting haha bye
Edit 2: Just to clarify, I love my dad, my mum loves him, and everyone in my family does. Life would be boring without him.
#32
My Dad - Has a small but relatively successful business. He was draining it to give all of the money to young women.
#33
I remember when my parents got divorced my dad started wearing cowboy boots and cologne.
#34
My 9th grade history teacher became an "insta-biker". He rolled up one day on a brand new Harley, and all the associated paraphernalia. Even as teenagers we kinda felt bad for him.
#35
Guy I used to work with had a mid life crisis and started day trading during work hours. He started making decent money from it and was phoning in his day job and really not putting in much effort. he eventually went to Turkey and got his hair and teeth done, dumped his rich, gorgeous trophy wife (he'd been living off her money for years and she even floated him when he started his own business, which he later sold for a tidy profit) and started living the single life, drinking with lads half his age and partying like he was some sort of superstar...
He's now living single, makes money, but is lonely, and his gorgeous ex wife is happy with a new man who probably can't believe his luck at finding a beautiful rich, independant woman in her mid 40s.
Upstaged75 7 hours ago
This is the 2nd one that mentions men going to Turkey to get hair and teeth done. Is that really a thing?
#36
My Uncle in the early 90's.
He was a very large man both vertically and horizontally. He swapped his sensible family car for a sports mini he could just about fit into and started wearing a pink and purple shell suit with white trainers.
Multa Nocte (she/her 8647) 7 hours ago
EVERYBODY wore pink and purple shell suits with white trainers in the early 90s, no matter their age.
#37
Guy turned 71 and picked up a 23 year old boyfriend. I've nothing against age gap relationships as a concept, but they're so toxic together it's unbearable. He even nicknamed the lad "Lambo", because "he's just like the car without the mileage".
#38
A man who became a doula to meet women. Not even kidding.
#39
My uncle was always such a mamas boy when I was growing up. He never dated or went to prom, drank, smoke, or anything like that. When he was in his 40s he suddenly bought a jeep and got all the different tops and doors that you could get, he put humongous tires on it, so much so my grandma needed a step ladder to get in even though she was in her 60s at the time. He put a loud sound system in it, started listening to things like Metallica. Would go to jeep jamborees. And he started drinking and going to bars. He eventually found a girlfriend during this time and got married and traded all that in for his usual stuff like restoring pinball/arcade machines.
Fellfromthemoon 3 hours ago
When was the last time listening to Metallica rebellious or a sign of midlife crisis?
#40
Fat, balding, 40 something guy with bad teeth and glasses has out of the blue decided to become a golf content creator / influencer.
Hangs about with much younger, more athletic types whilst his wife and kids are at home.
#41
A neighbour of mine drinking alcohol with her teenage daughter and her friends, and she is also dressing in her daughter’s clothes . All this whilst getting Botox and things. Absolutely disgraceful.
Lady Gypsy Rain 8 hours ago
I’m not so hung up on drinking with adult kids. It’s actually something I enjoy doing with my parents and my adult kids. We are at a stage in life where we are all equally legal and responsible adults. So unless she’s is drinking with underage kids or turned her place into the let’s get sloshed party house, I’m not hung up on this.
#42
My 50ish high school English teacher would add all of the departing seniors on instagram then would hit on a bunch of the girls.
He was kinda cool otherwise, which made it more pathetic.
#43
I know a guy who has been engaged 3 times in the past 5 years, they move in together and they soon break up but it’s never his fault.
#45
I'm sure there is much worse, but the one that affected me the most was my ex wife, who decided that she wasn't interested in me anymore and left me for the very first woman she ever went on a date with.
#46
Have you ever eaten a gallon of cookies and cream ice cream in one sitting? I have.
#47
I had a girlfriend for five years and we had twins and she got engaged within a week of meeting another man.
#48
TWO of my x-girlfriends from my youth who went on to get married and have kids with other men are now divorced and convinced that they are witches 🧙♀️.
#50
My grandpa had a late-life crisis after my grandmother passed away. He wrote and self-published a book of erotic stories. He passed out signed copies to everyone in the family. When he handed the book to my dad he said, “this might help spice things up in the bedroom” and I watched as my parents' souls left their bodies due to the cringe. It was funny and horrible to witness.
For what it’s worth, my grandpa wasn’t senile at this point. The man was as sharp as a tack. But he was also an accomplished troll. With that in mind, I don't know if this counts as cringy. Maybe just funny lol.
#51
The rare female mid-life crisis. The girl I used to hang about with in the pub decided she wanted to be a stand-up comedian. She used to be the hottest little emo girl you ever did see, but now she's middle aged andput on a lot of weight. But her comedy is about how hot and in demand she is. And its neither true nor funny. Feels desperate. .
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What do you think ?
David Paterson 1 hour ago
This is really encouraging. I now see that my own midlife crisis was very tame by comparison.
David Paterson 1 hour ago
This is really encouraging. I now see that my own midlife crisis was very tame by comparison.
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