What’s the biggest mistake you’ve watched someone make in their personal life?

  1. Must be my disabled brother who fell for an internet scam. He met a woman online, she lived in a different continent but he was certain she was the love of his life. Spent over a year chatting and e-mailing her, and helping her with money from time to time. Very fishy stuff, but he refused to listen to my scepticism. It ended when he had saved up enough money to go visit her. He went, came back 2 days later and refused to ever admit what had happened. Went to his grave without ever talking about it.

  2. Living in another continent asking for money definitely are red flags. So sad to see such thing happened.

  3. Something similar happened to my MIL. She’s 73 now, but about 4 years ago, she got divorced from her abusive husband. In 2020, she texted my husband and asked for $7k. My husband was like wtf why?! So she sent him this huge email detailing that she had met a man on Facebook who lived in some Asian country and his son was in prison and he needed money blah blah blah. Anyway, we found out she had sent these scammers $25k total. She lost nearly her entire savings and now has to live off a meager social security.

  4. This is the most disappointing one I've read so far. They were at least trying to better their situation instead of just being selfish dumbasses.

  5. Thats what scares me about moving. I wont move, or sell my house until u have significant equity to where this wont be an issue.

  6. When my grandmother died, my grandfather has about 15,000 dollars left over to live off of until he could no longer afford his house. My cousin heard that Grandpa had money, so he would ask Grandpa for “gas money” all the time, then go and blow it on drugs.

  7. This is really heartbreaking. Your grandpa had such a heart to where he would rather give money to your cousin to help him out rather than spend it on himself even though he didn't have much left to give just for him to turn like that. Hope he is doing better now.

  8. My buddy met a girl in college, who had a boyfriend. They got together. He ended up dropping out, got a random job. They decided to get married, from what I know he had 1 friend at the wedding, who was not me. Moved across the state away from his family. After like a year I met up with him for some drinks, within 3 weeks he told me he thought his marriage was over, pretty sure she cheated on him. Moved back home, took his life a year later.

  9. One of my best friends walked out on his wife and two kids because a girl at the gym and him were having a relationship.

  10. My friend gave up her full ride scholarship to play volleyball out of state because her cheating bf wasn't gonna be able to go to college with her. He left her not even a yr after she gave up her scholarship and now she lives in a constant what if because a couple of other friends have played volleyball around the world.

  11. My uncle got himself a mistress. Lent her $10,000 he never got back and lost his job defending her at work. Wife served him divorce papers short afterwards. He gave up his house to his wife. So he ended up jobless and homeless, sleeping on our couch at the ripe age of 60.

  12. Ugh, my uncle got himself one at 70. Seventy! Put all the assets in her name and then filed for divorce. Claimed he had nothing. My aunt had to go back to work at 67.

  13. A mistress in late 50's/early 60's wild to me. I'm 30 and I have no idea how these guys find the time, let alone the energy hahaha. Actually this is most mistress stories were the husband still spends a lot of time with family. I feel like your life would become all about "keeping the secret". Sounds exhausting.

  14. Friend worked hard to gain the credentials to advance his career to his goals. It took four months for him to get busted having an affair with a subordinate and he lost all he worked for and ended up losing his license.

  15. Single mother of 3 living in poverty. Gave her parents her $6000 tax refund to hold onto because she didn't want her abusive ex to convince her to split it with him.

  16. I cannot imagine a world in which I would spend my kid's money that they gave me for safe-keeping. Likewise I can't imagine a world in which my parents did that to me.

  17. One of my students was offered a 95% scholarship to Juilliard. They turned it down because they felt a 95% scholarship was a slap to the face, and instead decided not to go to school. Last I heard they weren’t playing, and were working minimum wage, but talking about how good they used to be.

  18. Burnt out? I mean, it's fookin' Juilliard. You toughed out 10+ years of playing to get an almost free ride at the household name of music schools, and you turned it down because it wasn't free? Four years, max. Four years. I've worked two shit jobs for three years each.

  19. A friend in high school got offered a 2 year football scholarship to college but turned it down because he would only take full ride scholarship offers. Well it never came. He’s the first one to graduate high school in his family, would’ve been the first one to go to college but let his ambition /pride get the best of him. He wasn’t that great of a football player either. Last I heard he was still working at the pizza restaurant he had been since high school and stuck with two kids.

  20. My parents getting re married (to different partners) when they have yet to figure their own shit out. They still haven't settled on custody of my younger siblings after going on 7 years now, and my fathers wife just moved out.

  21. My high school philosophy teacher cheated on his wife with my classmate. His daughter was in the year below us. She transferred schools out of embarrassment when her dad finally left the family to pursue a relationship with the 18-year old. Yuck.

  22. This girl who rented out my parents basement was not great at making smart life choices. She married someone who is serving life in prison for murder. She met him through her cousin who was also in prison. She eventually got a huge chest tattoo of his last name, and more tattoos of his name all over her body. He ended up being transfered to the east coast of Canada (she lived in the west coast) and she up and abandoned her 2 kids to be close to her husband. One of her kids is severely handicapped, but she never gave a shit about being a parent to her. Anyways, about 3 months after moving she posts all over her socials that they broke up, and she quickly tried getting the chest tattoo covered up. 2 weeks later she announced they worked it out and they were together again. They kept doing this pattern of fight, break up, make up and repeat. Again.. she had 2 daughters she up and abandoned for a man who will most likely never get out of prison.

  23. I'm willing to bet that her not being in their lives is probably an improvement. I hope they have someone who cares about them now.

  24. Let go of a girl close to their wedding because of his idea of what a wife should be like. Lives in deep regret now as she married his friend & they’re really happy whilst he has never found anyone else.

  25. A guy in his mid 50s always worked under the table. Never filed a tax return. Didn't understand that he wouldn't qualify for social security. When I showed him the requirements on the

  26. This happened to a guy I know who lived down the street. My ex husband FINALLY qualified for disability and was rewarded the max since his work history stretched back to when he was 13 years old. This guy always worked under the table or for cash, and couldn't understand why he couldn't also apply for disability and expect the same monthly amount when he hurt his knee.

  27. I heard about a pastor who filled out paperwork when he was ordained to be a "contentious objector" from social security (which apparently you can do when you are an ordained clergy person). Except he also didn't save anything for retirement. He was in his early 60s when he sat down with an accountant to talk about retirement. The accountant basically said, "nope, you can't retire".

  28. A buddy that live with me for a while got a car he couldn’t afford because he was obsessed with image. Stopped making payments, tried to part out the car and report as stolen since he had the bright idea that would bring more money than just giving it back to the bank. Then got into check fraud, which landed him in jail. Been in and out of the system ever since, from stories I hear.

  29. Reminded me of something similar without the fraud. My buddy had a decent car. His car got hit while parked outside. Insurance was going to give him a big payout. Got a rental car in the mean time. Parked it in the same place. Rental car gets hit and totaled. Didn’t bother to get accident protection/insurance on the rental.

  30. Here in Asia many people have kids so someone can take care of them in old age. I feel like I’m someone’s insurance and investment policy

  31. Yeah, let's go ahead and throw sleep deprivation on top of this already shaky marriage. That'll fix things!

  32. My friend failed psych evals to join the Army, once he got around that exception he was kicked out within a year. He robbed the corner store less than a mile from his house. He was in full SWAT gear with a tactical mask. Everyone knew exactly who it was, there were 8 calls to Crime Stoppers identifying him. He was arrested within 3 hours of the crime with the still loaded pistol in his car. If he had used a fake gun, or an unloaded pistol he would have gotten 1/2 or 1/4 the prison sentence. He went from being in the ARMY to prison in less than a month.

  33. Without going into too much detail, you need to be severely fucked up to fail the psych portion at MEPS. It’s computerized, adaptive, and there are plenty of “gimme” questions.

  34. The worrying thing here is that he “got around that exception” and was allowed in anyway despite clearly being mentally unstable…

  35. My brother ran for public office without having an agenda. He had no leadership qualifications, background in position, or support from anyone in the community. His took out a 10K personal loan to finance his political run and held one fundraiser where most of the attendees were family and couldn't vote for him. He lost badly, coming in last behind four other candidates. It took him years to pay back the loan and refill his savings, which he completely drained to pay for signage and flyers. Saddest of all, the printer misspelled his name on both items, so any remnant is a harsh reminder of how badly things went.

  36. My brother was getting scouted by Northeastern colleges to play football after playing remarkably well in high school….

  37. One girl I know inherited just under 100k...her grandmother passed away. This girl has serious mental health issues and is a druggie...blew all the money on drugs within 3 months.

  38. My friend got pregnant at 16. She convinced the father to have a second child with her because she wanted the kids to be close in age. So she has 2 kids by the time she turns 18.

  39. Just watched my cousin move out for the 5th time with no plan, no where to go, hanging out with manipulative people because they want her disability check. Cussed grandmother out when she tried to help and figure out what’s going on, got kicked out of one of the hardest community center to get placed in so now she DEFINITELY doesn’t have a home and has been sleeping in one of the most dangerous parks in town because drug addicts go there at night. Gonna try to talk to her tonight but honestly I don’t know what the fuck I’m supposed to do this has been continuous for months.

  40. I have a lady on my street who is around 35, and legally under the conservatorship of her older sister. She has a son that the sister technically has official custody of- though she watches and raises him in the same house, it’s a fail safe because she has legit problems.

  41. I went through this as well. I had a coworker that I became close friends with, she was doing well in her life: divorced and sharing custody of her 2 kids, not well off but didn’t have to rely on anyone to get by. Just living a middle class life.

  42. Dump all of their savings ($30k or so) into random crypto at the height of the market. They were trying to get more money to put towards a house but lost a majority of it when things crashed. When their significant other found out they left

  43. After that first sentence, I was like “hey, I don’t have strong preferences about a lot of things and so I like to just go with the flow. It works for me.”

  44. One of the biggest lessons I've learned over the course of my life is, "If you aren't planning on GOING somewhere, you END UP somewhere."

  45. There is a couple my husband and I used to know before we had kids. They were decent people and we hung out for a period of time, but then fell out of touch. I guess in the past decade they got hooked on heroin, had 2 kids, had those kids taken away by the CPS and now one of them is in prison. It really went to shit for them and there is really no one else to blame. Bad, BAD choices…

  46. going drunk on a floatable boat in the middle of the lake when you don't know how to swim, poor guy drowned.

  47. Similar thing happened to my friend. Went out fishing on a small boat on a beautiful day on the lake. Beautiful day turned into a huge wind storm, boat capsized, no life jackets. drowned. RIP T

  48. Some man tried jet skiing from Florida to the Bahamas or something like that during the hurricane. He's missing last headline i saw.

  49. A family member is notoriously awful at financial decisions and is obsessed with get rich quick schemes. He's the best example of why rich parents should never, ever give a 20 year old kid everything he could want. His formative years taught him that money was easy come, easy go and he never learned the value of researching before you buy or saving money.

  50. My youngest child's oldest friend: sweet, clever, funny, musical, could write code before most of his friends could count. Thought he could outsmart heroin. OD'd. Coma for 7 weeks, on hospice for several weeks, woke up at about 65 lbs (6'3"), now paralyzed.

  51. Knew a guy who's parents were like that. Mom didn't want kids, she wanted babies/toddlers. Basically lost most of her interest in them when they were 3-4

  52. My cousin went baby crazy at around 30. She was seeing this guy who everyone thought was just the biggest asshole, he was a short, angry, bigoted, sexist wanker who couldn't hold a job for long. The first time I met him the first thing he said to me was, 'nice car, how much do you make?' Not even hello.

  53. This was me until January of this year when I left my ex. I was a shell of my former self. If you feel like you have to be someone else to make a relationship work, get out!

  54. This is tough sometimes because people say "Don't change yourself for others." But it's also important to try and become a better person, to grow, to be responsible. And oftentimes you have no idea which of the two you're doing until it's too late.

  55. A next door neighbor owned a cabinet making business. An employee introduced him to crack. Within a year he let the business gradually fail, left his wife for her twin sister, was investigated by the IRS who found child porn on his business computers. He went away for a long long time.

  56. The IRS: “holy fuck I was just looking for evidence of tax fraud! This was supposed to be a boring investigation!”

  57. Watched a friend make €1.2M from a crypto coin of a €2000 investment and holding it all the way down to €50.000 over a month time while rage gambling the last 50K on a casino

  58. I worked in casinos for decades. Wildest story I ever saw was a guy came in and turned a grand into 20 one night. He was a supervisor from another casino on disability. Next night he won 200 000. This went on for weeks. When wins are that big, staff notice. He was up 3 or 4 million. Then I watched him lose it all back.

  59. When my mom asks my wife and I for a 2nd grandkid, I always ask her if she’ll give us the money to raise a 2nd kid. She shuts up right after.

  60. I watched a wasted guy throw 2K on a single roulette number, lose it, withdraw 5K more, and put it on the same number and lose it and then stare at the table. All while on a cruise ship. Then I went and had an old fashioned and it was wonderful.

  61. There's a way to get enjoyment without gambling. Watch other people lose everything and go and buy yourself a drink. Gives you the same sense of relief that you get when you wake up from a nightmare and realize you're fine.

  62. Meth is evil. It’s the devils candy. It lies to you telling you everything is great and you can do and be anything (first few times) then it has a hold and spins you out of control. It takes everything and everyone you love away and leaves you a spun out addicted meth head with nothing and no one to turn to.

  63. Watching right now. 2 coworkers are engaged and she is an absolute nightmare. I have known the guy a lot longer and cannot believe it has gone this far.

  64. I had a very talented high school student, he could create amazing paintings, and then the drugs came and he's not half the person he used to be. I hope he can overcome his addiction.

  65. Watched my sister make a few, but the biggest one was going out drinking after a bad breakup. She just could not let the guy go (he was separated when they were together, but ultimately got back together with his wife). She got hammered and called me to pick her up - I had taken night time cold medicine, which knocks me the hell out, so obviously I couldn’t drive to pick her up. She said that was fine, she would Uber. She lied, drove drunk to her exes house, got into a physical altercation with her exes wife, and left before the cops showed up. THEN drove the wrong way down a one way street and hit a concrete road block head on.

  66. My friend and i where hanging around one day. And he was talking about how his wife wanted to have a kid and if he didn't they should break up. He explaned that he didn't want to and wasnt sure he loved her anymore. She was already controlling (stuff like making him facetime so prove who he was with). Me and my other friend told him he should just call it quits and not have the kid. He did anyway because of low self worth and because he didn't want to shake up his life. Big surprise it got worse and worse. For a while. Then about a year ago he finally got the gumption to try and divorce her. Of course it was met with more hostility. Long story short he killed himself. I think back to the conversation we had all the time wishing i could have convinced him it was a bad idea. But i know thats wishful thinking.

  67. Definitely a shitty situation, but don't beat yourself up for it. You can't convince someone else how to live their life.

  68. Sorry for your loss. Don’t be too hard on yourself, you have tried . It’s his journey and his choice to make. Peace .

  69. Between this, relationship advice, and what could go wrong I feel pretty good about myself and how I've lived my life. Throw in a little personal finance and damn, I'm living the dream.

  70. My sister marrying her ex. Thank heavens she got out of that situation. It was really clear that she wanted to be loved, and he wanted to be taken care of.

  71. My sister lost her 3 kids due to an addiction to methamphetamine about 5 years ago. She complains nonstop about how the system stole her babies… while smoking meth to this day.

  72. A bunch of us normal potheads in our 20s and 3 of the 4 of us decided to smoke black tar heroin. It didn’t seem interesting to me as I loved pot and I’m not a grass is greener guy.

  73. Family friend quit their government job after 23 years, 2 years before qualifying for a pension. They did it just because they wanted a change.

  74. rush into a new marriage 1 year after his divorce... still getting to know the new spouse and finding they aren't as compatible as they first thought. lol

  75. I know a guy who got divorce #4 in November, met a girl, spent ONE DAY with her, then moved in with her the next day. It was a trainwreck for 5 months until they broke up, but at least he didn't marry her LOL.

  76. This is incredibly common. A lot of people have never functioned by themselves. They went straight from living with parents to a relationship cohabitation (maybe some roommate years in the middle).

  77. Having a child without a strong source of income or a stable partnership. I love this person and hope they're happy, but the whole situation spells disaster.

  78. My best friend didn't want to break up with a crackhead who literally stole from her to buy drugs, and who hit her once. :(

  79. Getting pregnant the first time you have sex from a one night stand from a shady grifter you barely know that bicycled to his McDonald’s job. She had a bright future. Now she’s struggling to even finish high school

  80. A buddy of mine (at the time) in the Navy met a girl who was vacationing in his hometown while he was home on leave. They banged for 3 days without getting to know each other. They talked for 2-3 months while she was sleeping with her ex. She up and left her parents house with all of her stuff including her handgun without telling a soul. Her parents freaked out and called the cops who found her at a motel halfway to the base we were stationed at. Being an adult they just checked up on her. My buddy married her the next weekend because she needed insurance as she had been off her antidepressants for a week or so. They were both drunk as hell when they got married. The best man/witness asked if my buddy wanted to go through with it and even offered to make it all just go away if he wasn't ready. At the "reception" the bride got up to use the bathroom and my buddy drunkenly admitted that he fucked up. I don't remember what lasted longer after that, his career in the Navy or the marriage as he got kicked out for stealing photos off of someone's phone.

  81. It’s waaay better to stay single and lonely, than be in a relationship for relationship’s sake. I’ve seen several people become less of themselves and completely devoid of their personality because they chose to be with the wrong partners.

  82. Good friend messed around with a young Brazilian woman whose ulterior motive was to get married to stay in US. She got pregnant. He wouldn't marry her even after baby born, so she moved back to Brazil.

  83. My former best friend fell into drugs after his wife killed two people while drunk driving. His wife went to jail, he lost custody of his kids because he couldn't handle everything alone, he got into drugs real bad and started stealing from everyone around him to support the habit. He managed to steal about $7k from me, but another aquaintance lost $32k. While in this "death spiral," he managed to screw over about 30-40 people to a tune of around $300k total while obliterating his business at the same time. He wound up in jail over it.

  84. Hoarding. I have a friend who jammed her condo so full of useless shit she bought and bought and bought. The pace is 1500 sq ft but she only has about 6 sq ft of space to live. It's frightening.

  85. 15 feet away. High stakes, low chance of succeeding without detection. Some motherfuckers live to dance on the edge of a razor.

  86. I heard my college roommate’s one night stand tell him he didn’t need a condom because she was “clean” and it was “the safe part of her cycle.”

  87. Several times seen women marry soldiers and get pregnant right before they head off to boot camp. The guy gets deployed and of course comes back different. Eventual divorce and essentially single motherhood.

  88. My best friend have just left his wife with two children (been together for 18 years) for my now ex-girlfriend.

  89. So a friend got baby trapped by his abusive ex girlfriend. Basically he semi-ended it before he actually realised she was abusive. She blackmailed him into paying her rent by getting his mother to be her guarantor, and then telling him she wasn't going to pay. My idiot friend slept with her after telling her he couldn't pay her rent any more,after over a year. She provided the condom.

  90. I don't know what changed him exactly, but he started calling himself an alpha male, and questioning any activity, clothing choice, type of car, career path, drink, etc as alpha or not. He bulked up and got large muscles but also still carries a beer gut. He tries to have his shirt off whenever possible, but it doesn't work for his body type.

  91. Proposed to his girlfriend after she had cheated on him. Two months before their wedding she left him and immediately got pregnant by a random dude.

  92. Thinking that "big man on campus" in a small town means that ur big man everywhere. It destroyed 2 of them in my small town when they realized they weren't the biggest and fastest and ppl weren't going to give them everything they wanted just cuz they were who they were. 1 drank themselves to death, the other is 1/3 his HS size and looks like a meth head.

  93. My wife just had a c-section, and was complaining about a pain in her leg but never got it checked out. Two weeks later; Blood Clot.

  94. My brother, in his early 20s and just getting out of nursing school, living in Alabama (which he hates), meets and marries a pregnant southern girl, lets the bio father sign away his rights, and adopts the baby. In the end, the kid has an actual dad, which is great. But to this day he bitches about not being able to leave Alabama, and I remember us all telling him he was being dumb when he was doing this.

  95. Give up their dream career because their jealous, controlling spouse didn't want them to ever be away from home. They've basically lost contact with all their family and friends because their spouse doesn't let them do anything except go to work and take care of the kids.

  96. I'm a Financial Advisor for a certain company. I guy who was my roommate during training got the deal of a lifetime. A 30 year vet was retiring and basically just giving him his book of business. At the age of 23, my buddy would be making somewhere between $1-$1.5 Million a year. The hard part is building the business. Once it's built it's basically a cake walk. Unlimited vacation and time off, make your own time and hours. I mean, literally the best life you can imagine.

  97. I have a cheapskate uncle that spent his life saving into a junk bond, compounding the interest, putting all his income in and living like an absolute beggar, even as he became a millionaire. You might be thinking to yourself "nothing wrong with frugality". No it is more than that, he used to come to my parent's house, spend the entire day eating our food, and not leaving before my mother packed him more food for the week for free(my mom's fault for not setting harder boundaries too).

  98. I did this once. Had history with a girl but it didn’t work out the first time. We reconnected over facebook and she literally moved three states over to where I live on a whim. I told her she couldn’t live with me but she stayed the night because she didn’t have a bed yet. Then she stayed the next night too. She ended up not sleeping one single night in the apartment she paid for 6 months.

  99. My Aunt is in the process of selling her house, and buying a camper van. I'd say that comes really close.

  100. my father "staying" in the marriage with my toxic mother, despite planning to leave her when I was old enough" (like 16 or sth), when I was only 2 years old.

  101. Someone I love is so afraid of the stigma she REFUSES to get mental help. (Can’t be diagnosed “the shame!”) so she suffers terribly. Had it all, loyal good looking husband. Lots of money in the bank- $6000 every month & she could spend it (and would spend it) on nothing/everything. No real responsibility retired at 42. 4 kids, 8 grandkids, all pretty healthy and stable. Found her lying in the closet surrounded by furs SOBBING and suicidal. I should have called 911 & had her committed. Maybe she’d be medicated and managed. I didn’t want her to hate me. She hates me now anyway, has divorced her husband has less than half the money available and has isolated herself from her kids. We both fucked up. I should have taken her in. She should have gone when we all begged her too. Paranoid delusions are a bitch.

  102. Watched a good friend I'd known for years marry an utter control freak who, within a year, had systematically disconnected him from his "old" friends and even some of his family. Then they moved out of state so they could be closer to HER friends and family.

  103. Middle aged guy was living the dream in a $15 million house, multiple boats, owned a very successful business, had a beautiful wife and kids.

  104. My friend got addicted to hard drugs. We all smoked weed, but he took it way too far. He overdosed on codeine, died for 6 minutes, and developed sevier schizophrenia and siezures. Now he can't hold a job let alone walk down the street without looking/ sounding like a crazy person.

  105. I'm so sorry this happened. How old was he? I'm curious if he had symptoms of Schizophrenia and he was using drugs as a coping mechanism? Now that he's (hopefully) not using drugs he can no longer avoid the symptoms?

  106. I watched my friend throw an engineering career with Boeing away because he decided to smoke a bowl to celebrate getting the job. It was a military contract.

  107. How are you smart enough to get an engineering job at Boeing, but not smart enough to know they drug test? Especially on a military contract??

  108. I don't smoke and this happened to me, without thinking I took an small edible for no reason (which I partake maybe once a year) while under an interview process for a company. After realizing my mistake the next day I was scared shitless and tried everything under the sun to flush my system. From running extensively to eating very strict meals. At the end.. they didn't even test but I was going to pass anyways, the amount was too small and was not detectable after a week.

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