51 Of The Most Spectacularly Cringe Midlife Crises People Have Witnessed

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 😭.

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. .

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.

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.

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.

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.

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.

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.

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.

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.

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. .

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.

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.

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.

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.

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.

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.

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.

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!

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.