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“My Mom Started Dating A Woman”: 58 People Who Took Their Midlife Crisis To An Absolutely Unhinged Level
Teenagers are famous for going through rebellious phases and making choices that leave everyone around them wondering what on earth they were thinking. But grown-ups aren’t immune to making a few questionable decisions themselves. Except when an adult goes off the rails, there’s usually a lot more on the line than a bad haircut or an argument with your parents.
One Redditor asked people to share the most intense midlife crises they’d ever witnessed, and plenty had unforgettable stories. Some were disastrous, while others actually changed someone’s life for the better. We’ve rounded up some of the wildest ones below. Scroll down to read them.
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#1
My mom turned 50, started menopause. Started dating a woman and moved her into our house, left real estate and bought a restaurant with her partner, left me and my sisters on our own for at least a week every month to go on extravagant cruises and trips with partner, basically threw all caution to the wind- it was actually really difficult and kind of [messed] me up throughout my high school years.
That being said, she got leukemia at around the age of 60 and [passed away] within 2 years so I am glad that she had a chance to see the world and take big risks.
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#2
Former friend decided to tell his wife he wants to move other women (who he will impregnate) onto their property and be the only male with all these other women and father of all these children. His wife left with the kids and so far no other women are willing to sit in tents and wait to be impregnated by his lordship. What an idiot.
#3
Heard about this one guy who bought the world's biggest social media platform for 40 billion dollars and then completely tanked it.
#4
Probably my own, ended up getting my entire face tattooed and head tattooed, like all of it. No ragrets though.
#5
Dad quit his job to buy a farm with his pension fund, couldn't afford it and now lives in a caravan.
#6
My dad cheated on my mom with a coworker who was 15 years younger than him. He bought another house, took another job across the country, and spent YEARS living with her while still married to my mom, saying he "wasn't sure" if he wanted to be married anymore. Divorce papers drawn up twice but never signed. Eventually he left the other woman and he and my mom have been back together for a decade.
I have no idea why my mom stayed with him and I'll never understand it, but I've pretty much told them that I'm not interested in discussing it with them any further to keep the peace.
#7
Neighbors wife left him, took the kids with her too. The guy lost like a 100lb, replaced a VW minivan with a sporty BMW, got a pinball machine and a cat that he now casually walks on a leash outside. He forgot to get a hot blonde with double Ds, or at least I haven’t seen one.
Proud of him.
#8
My father’s, he cheated on my mother with a younger coworker and imploded our lives. They eventually married but the joke’s on him, I know for a fact that he’s absolutely miserable in the marriage.
#9
I knew a woman that got divorced at 38, lost fifty pounds, won a fellowship to start a PhD, bought a motorcycle, and got all the tattoos she ever wanted. Still a great mom to her kiddo, just happy and thriving. Total legend.
#10
A friend’s father was the embodiment of the perfect family man throughout my childhood. They were all tennis players. My friend became a doctor, his sister a judge, and his younger brother an engineer. They were perfect at everything (and they were all blond with blue eyes too, I’m not even kidding).
Then when he hit his fifties, this family man I knew quite well, since I’d spent half my childhood at their house, completely lost it. He left everything behind. My friend would occasionally see him around town, completely wasted, not alcohol. He hung out with sailors who were in port and would get absolutely hammered with them.
My friend later found out that he had started a relationship with a man. He eventually moved to another city, and a few years later we heard that he had passed away at a relatively young age. My friend never wanted to tell us how he passed away. Obviously, we didn’t push him on it.
For this guy, the midlife crisis was just too much. Or maybe he had kept all of that bottled up for decades while playing the role of the perfect dad in the perfect family. Either way, the explosion was brutal.
#11
19 years married with children, took one last overseas military assignment by himself, so as to not interrupt his family's life. Went overseas met a 20 something local hottie and completely ghosted his family. Wife was calling family and military trying to figure out what the heck. Led to divorce, married hottie, she didn’t want to move to USA so single and taken to the cleaners.
#12
I grew up in a small town in the early 80's. There was a very Flanders-like family of ultra Christian do-gooders who all dressed alike. All of the women (and young girls) in the family had matching beehive hairdos. They announced all of their birthdays/anniversaries/whatnot on the local cable scrolling text channel (remember those?) and generally tried to do an impression of the Osmonds.
They were pretty harmless, but seriously annoying.
I went to school with the oldest daughter.
When we were juniors in High School, the dad just split and vanished. It turned out he had *another* creepy family in another town whom he decided he preferred.
The left-behind family didn't know how to cope, and spiraled pretty seriously.
#13
My dad left my mom for his childhood neighbor, quit his high power tech job and built a cabin in the Alaskan wilderness. I'm not mad I just wish he would call occasionally. Hopefully he found happiness.
#14
I had a spanish teacher in highschool he was in his 50s and wore khakis and sweater vests/button ups every day very clean cut with a mustache just like normal tv dad. He showed up one day in a corvette. (He had some old family money) then the following week he showed up in jnco's with blue hair and long dangly earings. He came up to my desk put his hand on my shoulder and said youre gonna do good. Then left the classroom. We never saw him again. Then like a year later he took a flight by himself, he was an instructor, and the plane crashed. His body was never recovered but the wreckage was. 10 or so years later he was found in south america alive and well.
#15
My middle class, suburban dad had his midlife crisis while Sons of Anarchy was on TV. He bought a Harley and 10 years later he was patched in to the Hells Angels. I wish I was joking.
#16
My male BFF getting a full facelift just because his daughter's friend said he looked old at 52. Now he looks different and in a Mickey Rourke way.
#17
My mother had an affair with a man at work and ran off with him. Then came back trying to fight for custody of the kids she abandoned. She ended up married a total of 7 times before she got too old to attract any other men.
#18
Girl I went to highschool with had the classic dad ran off sitch with a much younger, Vietnamese woman. He had lost a bunch of weight and thought he was hot [stuff].
Jokes on him cause his ex wife had the glow up of the century, and last I heard was shacking up with a younger professional chef who was treating her like a queen. Meanwhile, dad was given the bait and switch and was made the de facto bread winner for the new girl’s whole family back in Nam, and hates his life.
Dude was cop and drained his pension early.
#19
I know a guy who divorced his wife of 20 years, left the country and moved to China to marry a woman 22 years younger than him (he met her on a prior trip less than a year earlier.) Only lasted a few years, returned to the States after paying her out over $50k to leave him alone.
#20
Dad's friend quit his well-paying engineering job to become a mountaineer in Alaska. Now, he works as a park ranger last I heard. Divorced his wife and cut off all contact with his daughter as well.
Very strange and rather sad.
#21
My mom. She was a virgin when she met my dad and super religious. So religious I grew up in a Christian non denominational cult.
She never drank or did any thing that was considered secular. Her whole adult life revolved around church.
My parents were crazy strict on me and never let me do anything in middle school and high school. Dating was completely forbidden. My parents both were obsessed with purity culture.
Well, when my mom turned 50 she had an affair with her 1st cousin! She stole a lot of money from my parent’s joint account and gave it to her lover. She also started smoking and drinking heavily.
She started going out all of the time and divorced my dad. Since her divorce with my dad, she has been married three times and is a completely different person.
#22
Lifelong bachelor decided at 55 that life was empty and ordered himself a bride from one of the countries in the former Yugoslavia. She's a lovely woman who gave him a son. His son is autistic but high functioning and they seemed to be a loving family. Unfortunately, the man passed after a VERY quick battle with prostate cancer just a few weeks after his 70th birthday.
#23
My dad lost a legal battle with his work occupation, and so lost his license for his work. He proceeded to strip and burn all his old work documents in my back garden in one of those hobo bins while dancing around. Had friends around that day so was not expecting that when we opened the curtains to my back garden for them all to see my dad prancing around a fire. Good times.
#24
Not too intense per se. But I had a middle-aged coworker who literally moved cities specifically for that job. Just to work for that company. And then maybe 4-5 months into it she just froze up for a couple of minds, then stood up, said "I'm sorry, I can't do this" and just walked out in the middle of the day, and we never saw her again.
I don't think she planned, it or had anything lined up. I think for a moment she saw the world and her place in it with absolute clarity, and opted for a significant and immediate change. And I kinda respect that.
#25
A buddy of mine buying 3 new Harleys and modifying them to be extremely loud so that everyone turns around as he passes by. He's approaching 50. Every time he parks he revs it one last time.
#26
Friend quit his high paying corporate job on a whim, left Chicago to move to Bolivia with plans to learn Spanish and open a bar.
6 weeks later, he returns to Chicago, gets a server job at TGIFridays and moves in with his mom.
It’s been 3 years, he’s still waiting tables and rooming with his mom- definitely does not seem to be living his best life.
#27
A guy I knew suddenly sold his house, bought a sports car, quit his job and announced he was moving to another country to “start over.” Six months later he was back, living with his brother, working the same type of job, and still making payments on the car. It was like watching someone speedrun a midlife crisis.
#28
My mom got depressed about all her kids starting to grow up and leave the nest. So first she started trying to mother our friends, then one day spontaneously moved out of the house. Little under a year later and the grapevine informs us that she's visibly pregnant.
My dad is doing well now but that was a really rough year for him.
On Dad's insistence we didn't cut her out; it's been a couple decades and we've mostly moved past it, but her relationship with all of us will never be the same and she knows it.
#29
I’d say 3/4 life crisis. My dad left his long time partner of 22 years for a woman he met online who lives in Boston (he lives in Ny). And now is spending the majority of life traveling back and forth from Boston. She barely speaks English. He’s insane.
#30
Buddy of mines father, business owner, fairly wealthy, car collector. His spouse cheated on him and somehow was awarded half of his belongings, cars included. He took all of his cars one by one, drove out from the garage, floored it through their back lawn and jumped out into the grass and sent them all into a lake/river thing that went through the area. 7 cars total, one was a Bently, which his wife wanted most.
We were just watching from his bedroom window over the course of about 30min. My buddy called his dad, dad was super calm and was like "oh, just just taking out some trash" as we hear him firing up the next car in the garage.
His dad then proceeded to start taking a sledgehammer to all the walls in the house while laughing and crying, then abruptly stopping that attitude when anyone spoke to him only to start back up as you turned around. It was wild.
#31
Neighbor got into his early 50’s and suddenly decided to get into his families roots. He traced his lineage back to Ghana and went to visit. Came back, decided to quit his high ranking job at a very prestigious university and bought land to farm in Ghana. He will leave for 3-6 months, come back and be miserable for a few months and then go back. Basically said his kids are over 18 now and don’t need him and his wife can join him in Ghana if she wants…she does not want.
#32
Currently my dad. Forty years married to my mother, childhood sweethearts so had dated years before marriage. Had a very nice home, quite a fortune saved in the bank, opportunities to travel globally for work to add to the life of luxury….threw it all away for some Zambian woman who didn’t have a penny to her name and insists my father shows his devotion to her by buying her everything she wants and demands including a very expensive home built from scratch.
Now divorced from my mother and currently still working (Despite a decade ago saying he really wants to retire early) because the woman has spent a large amount of his savings already and has isolated him from not only me and his grandchildren but the rest of his family (We’re South Asian so there’s a lot of us and we’re all really close and involved daily in each others lives). I’m honestly waiting for the fallout to happen just so I can say “Told you so” because the last time I saw him, which was the first time in five years, he looked stressed and miserable, a shadow of his former self.
Unfortunately he’s too stubborn to admit he [messed] up and my mother still continues to thrive and still very much apart of the larger family’s lives even though they’re now divorced.
Maybe I’ll come back in five years with an update.
#33
Quit their job and enrolled in seminary school, 3 hours from their kids and is living in a dorm room.
#34
My cousin got an apartment with it telling anyone and moved away from her husband who owns the house and kids because she wants to have a hot girl life. She has 4 kids and a bunch of cats in the house that her husband has to now take care of. This is an evolving story as it is happening live.
#35
Spouse of a family friend one day decided she never got to enjoy their 20s. Left her job and family to become a groupie, started dating people half their age and going to any show/concert they could find. Roughly a year later she tried to get back with her spouse and family acting like it wasn't a big deal but ended being served divorce papers instead.
Haven't seen their family in a few years but last I heard is the kids don't want anything to do with her and the dad found someone new.
#36
My Dad at 57 separated from my mother due to an uncontrollable gambling and then married a younger woman in her 20s two years ago, had a kid with her and then passed away from a heart attack 6 months ago.
We get nothing from the inheritance either. Devastating not being able to visit the house I grew up in.
#37
My uncle. He was orphaned as a child alongside his 4 siblings, he migrated to the US, achieved the "American dream" by owning a successful business, bought a home for his wife and 5 children, and was even a small radio personality in his town. In his 50's he got into [illegal substances], his wife and kids inevitably left him, he got arrested on a dui, lost all his businesses, his home, and ended up tweaked out, shirtless, and shoeless, rambling nonsense outside the street he had his business at. We buried him last month, as he died on the street of unknown causes. RIP uncle Beto. I hope you are at peace now.
#38
Guy turned up to my dads martial arts gym wearing a full ninja outfit with his hair slicked like Steven Seagal in his early movies.
He yelled "USS" and made Bruce Lee noises when performing moves.
Also brought his katana but my dad made him leave it in his truck.
#39
Mine. Laid off from a decade long tech job in SF (was automated). Parents convinced me to move back home for a "soft landing" only for me to walk into the wasp's nest of their marital breakdown.
They used me at a sound board to all their grievances about each other. I got thrown under the bus. They got divorced (after 40+ years of marriage). My Dad tried to physically fight me, I figured out a way to remove him from the deed and assets so he wouldn't leave us homeless. I no longer talk to my Dad, and he ended up moving out of state. I blocked him across all channels.
I tried to regain employment in my former industry but there was nothing left. SF was no longer viable for me. Gone was my social circle, stability, etc... all left in SF.
I had also had a late stage autism diagnosis, resulted in unmasking and losing my identity for awhile. I dissociated and went full Britney: shaved my head and eyebrows. Heavy cannabis use, sometimes ketamine. Starting vaping nicotine. (fortunately I had quit alcohol prior to all this)
I blew all my savings to build a casita on my Mom's property. Getting a job again seemed impossible as I was also dealing with ageism.
I blew the rest of my money shopping, spontaneous vacations to escape. Drained my Roth, drained my 401k.
When I came out of the years long dissociation I bought a Rat Rod with the little money I had left. No safety features, no seatbelts. But it was actually the joy my vehicles brought that started to turn everything around.
I started my own business purely on credit, became a baker. Still not profitable but things are starting to moving forward. Never looking back.
#40
A guy I was sorta-friends with in the Army and who ETSed a few years after me.
For most of his retirement, he worked as the manager of a furniture store. Always wore polo shirts, stayed clean shaven. His only tattoos were on his chest and upper arms, not visible even in short sleeves. Was very much a straight-laced, white middle-class suburban dad. Even drove a Volvo station wagon. Had a son in 2005, had a daughter in 2011.
Come 2020, the daughter [passed away] of cancer and his wife divorced him. Son went to live with his grandfather. Apparently there were issues between him and his son, but I don't know the details.
He ended up quitting his job and selling his house and bought a cheap condo in a poorer area. Used the funds from the home sale to buy a Harley and some other [stuff] (a few guns, tools, stuff like that). He grew a beard, got more ink including a full sleeve, got a job as a motorcycle mechanic (he was always a quick study) and ended up prospecting for the Mongols by 2021.
He got patched in around mid-2024, got arrested in early 2025 for having 5kg of booger sugar in his saddle bags. Club ponied up his bail money and got him a lawyer. Three months later he got arrested again for beating a fellow club member with a steel-toed work boot. The club was understandably unwilling to pay for his lawyer/bail this time.
I'm just waiting on the news that he got shanked in prison at this point. I feel bad for the son. Hell, I feel bad for my guy, too.
#41
Divorced my husband, went no-contact with my family, sold my cafe, married my old boss, bought a sports car, became a butcher. I love my life now, but it was a lot.
#42
My dad left my mom one morning right after he finished his degree and got a new better paying job. She supported our family while he went back to school. He played the victim and cut ties with me saying my mind had been poisoned against him. I found out he moved in with a woman he met at the new job that very morning.
#43
Sold my company stock and bought a Porsche. Paid it off. Contemplating leaving my job to live on a yacht. Either that or start my own business.
#44
My own?
I came out as non-binary and started on HRT then a few years later I quit a decades long career to spend the entire summer hiking and camping with my dog after a coworker [took their own life].
Decided there were more important things in life than making money and I needed to take some time to just live.
My dog passed away two years later, and I couldn’t be happier that I made that decision.
Back working now but it was a pretty intense midlife crisis. Oh and during all that I got my motorcycle endorsement and ride a dual sport solo deep into the wilds of Montana on a regular basis now.
I’m not quite sure how my life turned out so wild so quickly. I also put on a lot of weight and need to get a handle on that somehow.
#45
I worked with a married guy who fell hard for this female co-worker. Dude gave his old car to his wife, bought a sports car. Started to dye his hair and change clothes. She had no interest in him but was just being friendly. It was a hard realization when he realized that it's just being friendly. It was kinda funny.
#46
One of my coworkers divorced his wife of (idk but maybe 15-20) years and 6 months later married his very attractive 24 year old assistant. She did *really* well in their later divorce settlement and now he has two alimonies instead of none.
#47
High school buddy of mine had one of those perfect looking marriages. Wife cheated on him after 12 years and he went off the deep end after the divorce. Bought a $100k truck, started doing steroids and got super jacked, dated a series of 19-22 year old girls in his late 30s. At least a couple of them were only fans girls, I can only assume it was a sugar daddy kind of setup. Only good thing was they didn't have kids to get dragged into that. He snapped out of it just before 40. It was over 2 years of debauchery.
#48
My own.
I never really thought about age, at least not existentially, until I turned 45. A few weeks after my birthday in a conversation I said, ‘heck yah, halfway to 90.’ to a friend and somehow it just stuck in my head.
I crashed hard, I nearly lost my career, my partner, I stopped taking care of myself and even spent some time in county jail.
The human mind is incredibly powerful and you can trick yourself into believing most anything. So trick yourself to believe everything is fine.
All charges were dropped and expunged, still 45 and crushing life again.
#49
Cousin wife cheated on him, she left with the kids.
Guy decided to buy every "toy" under the sun. (Boat, motorcycle,sport car...) and get tattos all over his body to show her how cool he is and what she missed.
All this under credit cards.
He is now full in debt and still beghing her to come back.
#51
Only my own.
I completely dropped a potentially lucrative career path (Aircraft Avionics maintenance from 20 years in the air force) to go to college (for the first time) in an unrelated field (Computer Science) that only barely touches on relevant experience to carry over.
This was all following a complete mental breakdown that has had me spiraling into severe depression over the past four and a half years since retiring. I'm still recovering from that.
I'm 48 years old.
One (other) positive thing that came out of it is that I quit booze (4 years sober now) after over a decade of extreme alcoholism.
#52
I met a guy on the job once. I noticed he had trouble moving his arms and asked if everything was fine. "Not really". He said.
He told me that when he became 50 he had a first hand experience of life crisis.
His "crisis" was a motorcycle he always had wanted. He had tried to buy it when he was young and still living with his parents, but his mum said no. Then he needed the money to get married. Then he became a father and he had a mortgage.
At 50 he felt he was finally free and bought that motorcycle. First day on the street he went out and started driving as fast as he could. He told that he knew it he shouldn't have, but he just couldn't help it.
Eventually he hit with his left arm a car coming from the other side. He fell and almost passed away, his arm badly wounded.
His wife went to the hospital and once she understood he was fine she threatened to divorce him.
He told me:"She was right. She should probably do it. Because if I had a chance to go once again on that moto, I'm not sure I would be able to drive slow".
Lucid madness.
#53
My elementary school's founder's "ex" husband was the works; dated a woman 1/3 his age, decked out in tacky luxury brands, luxury cars, all concluded with a raid in one of his houses for illegal possession of a bunch of weapons.
I got invited to his kid's wedding and they're witholding the address of the venue, even to us guests because they're afraid the old man is gonna cause some drama.
#54
He questioned his sexuality, ran off all of his friends, purchased dating apps, cheated with a coworker and beat his wife when she caught on to everything. He’s now completely alone and denies any wrongdoing.
#55
Started a business and grew it to a million dollar valuation with multiple locations. Made few wrong decisions and bankrupt at the age of 38. Literally, no money to buy even one cigarette so I had to quit smoking. Moved back to live with my parents. Lived there for 8 months and finally moved out to start fresh.
#56
Dude quit corporate to be an achyuasca shaman in Brazil. Has a business where he sets up trips for business people to go do psychedelics in the jungle now and he guides them or whatever lol. Dude I met in college.
He seems happy tho lol so I think it worked out for him.
#57
My dad forced us to move across the country despite not wanting us, dumped us in the middle of nowhere, bought himself a six figure condo over 400 miles away, and would expect us to make the 400 miles trip to see him 2x a month to just brag to us how great his life is without us.... He truly thought we were holding him back from his party lifestyle of booze, travel and women.
#58
I worked in a Tailor shop and this 60 year old woman came in for a dress fitting for her niece's wedding.
The dress ended up being a bejeweled wide weave net dress.
She just had her bra and panties on so as I was pinning it i asked how much room would I need to leave to fit the slip underneath.....
Nope. She was 100% planning on wearing this sparkly fishing net with her skin colored underwear to a formal black tie family wedding!
Her reasoning was that she saw celebrities wearing that style to award shows, and red carpet = black tie.
Yikes.
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