Cautionary Fails: Regrettable Times People Ruined Their Lives in an Instant

Sometimes the dumbest mistakes have the gravest, most life-ruining consequences. You never know when one seemingly small (although bad) choice might land you in prison for thirty years, or totally bankrupt, or worse—dead. One redditor asked the internet, "what is the fastest way you have seen someone ruin their life?" and the resulting thread is full of cautionary fails that all of you should keep in the back of your minds the next time you're tempted to take a high-risk, low-reward shortcut in life. 

Author image for Mel Dawn Mel Dawn
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  • 01
    Font - r/AskReddit u/fluffy_upvote • 1d [serious] What is the fastest way you have seen someone ruin their life? Serious Replies Only 24.4k ↓ 13.8k ↑ Share T
    via r/AskReddit
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  • 02
    Font - princhester 1d I'm a lawyer. Another well respected lawyer in my jurisdiction was involved in an absolutely huge property settlement involving dozens upon dozens of deeds, side agreements, financial documents, yada yada yada. The whole lot (presumably involving literally a hundred or so signatures) had been signed off by her client. In the early hours of the morning - having no doubt slaved away for untold hours getting everything ready for the settlement the next day - she must have real
    via r/AskReddit

    "I can understand this. so tempting, so easy to do and yet disastrous consequences." said u/Objective_Number2519

  • 03
    Font - jadenwydbro. 1d Watched a guy gamble $30k away in a night and then cried about losing his life savings and security had to get involved and escort him out because he started to get angry at the dealers because all they could offer him was free night stays at the hotel for playing so much but he wanted freeplay at the tables/slots and they refused Reply 10.9k ↓
    via r/AskReddit

    "Any money you plan to gamble should be money you already consider spent and gone." said u/travis373.

  • 04
    Font - Cmsmks 1d ● Watched a buddy spend his entire life savings betting on the Paulo Costa Vs Adesanya. I begged him not to do it and he lost his and his wife's entire 60k nest egg. She left him immediately with the kids and now he lives at his moms house. EDIT: wow this blew up. So a little more back story. He had been betting on prize fighting for a short while and winning. Nothing outrageous and heck I even bet with him on a time or two because it was smaller bets 1-200. He had been winning
    via r/AskReddit

    "Holy shit, he bet on Costa?!? That somehow makes it even worse." said u/Nubsondubs.

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  • 05
    Font - SafariNZ 1d Arrive at work on their first day as a temp at around 10am, caught stealing the bosses wallet at 12:30, taken away by Police at 1pm Reply 20.7k ↓
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  • 06
    Human body - So_spoke_the_wizard • 1d The kid in the national guard posting gov't secrets online for internet cred. ... Reply 9.9k ↓
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  • 07
    Font - missiondivorcee . 1d 15-20 years ago, an ex worked at a dream job type of place. If you make it professionally in that field, this employer was/is the absolute peak, there is no better place to go. New guy started there, on ex's team, right out of university. His first day he went to the company store and got ALL the gear with company's name on it- tshirt, hat, socks, etc- and proudly put it all on. After work, team took the new guy out to drinks to celebrate his first day at dream job em
    via r/AskReddit
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  • 08

    (Continued)

    Font - EDIT: The bar was in a never gentrified, always wealthy part of SF, CA. Patrons were very wealthy people, entitled. Myself, Having worked in fine dining in college, I can only imagine the absolute HELL those patrons raised about seeing some dipshit's dick while slurping down their 3rd martini. Many of you relate to this story, and have shared about not even wearing something as small as a lanyard w/ company info on it. This is all great logic, please keep it up and share that advice. It i
    via r/AskReddit
  • 09
    Font - satansfloorbuffer. 1d I wound up having to change the number for my first real cell phone, because the previous owner of that number still kept giving it out. Apparently she had just moved, and her old job couldn't get ahold of her to send her her last check. Her new job couldn't get ahold of her to get her schedule. Her vet couldn't get her to pick up her cat. I got calls from her leasing company who needed documentation to secure her apartment. Ever single day was some new way an idiot
    via r/AskReddit
  • 10
    Font - jwardtitan92. 1d My father in law is 65. Was married to his wife for 37 years and has 3 daughters. The picture perfect family from the outside looking in. He was well respected in his career field and was also an interim pastor/deacon at our local church. After he retired his health started to deteriorate drastically and he started drinking. This past November we learned that he had fell for a "love scam" on Faceboo and had spent his entire life savings, took out a second mortgage on his
    via r/AskReddit
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  • 11
    Font - ApprehensiveVirus125 • 1d Bar fight. Heard a loud commotion for about 30 seconds. Some guy thought this guy was hitting on his date. Suckered punched him. The other guy fell down and clipped the bar. The bar had brass foot rest at the base. Snapped the guys neck so loud you could hear it across the room. Reply 3.7k ↓
    via r/AskReddit
  • 12
    Font - notreallylucy • 1d An acquaintance. He had a good job, nice truck, mortgage on a nice home, minimal debt, in a relationship with someone out of his league. Before I knew him he'd had a DUI, but his attorney got him a plea deal that dropped the DUI down to a minor charge. A real lucky break. All he had to do was stay the course. He could have walked home that night. It was less than two miles. But he was too proud to leave his truck at the bar, so instead he wrapped it around a power pole.
    via r/AskReddit
  • 13

    (Continued)

    Font - There was prison, then a year on house arrest. His job required a driver license, so that was gone. I don't know at what point in his house arrest he could have started working, but he refused to. His former employer offered him a non-driving job, less money but still good money. He turned it down because it was beneath him. He said the same thing to two jobs his girlfriend singlehandedly secured for him. Even after his house arrest, he refused to work. He said he didn't want to. Apparent
    via r/AskReddit
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  • 14
    Font - Dudethefood. 1d An old customer got fired from Uber and DD for being slow/arriving with cold food way too often. Comes into my bar the next day with limited edition XO Weeknd sweater + jeans, new apple watch and new iphone all paid cash. Says he took out a payday loan for $10k and doesn't intend to pay it back, he'll just cancel the bank account. His exact words "Who needs credit anyways?". He stopped showing up to the bar after about 3 months - Never saw him again. Edit: For those asking
    via r/AskReddit
  • 15
    Font - Important_Stroke_myc. 1d Crime, specifically felonies. My lawyer took out a loan forging my signature. He's doing 15 years in federal prison. I would have given him the $5000. His kid was very sick and I would have gladly helped him out. ← Reply 7.4k ↓
    via r/AskReddit
  • 16
    Font - Innohurrytodie. 1d A coworker sent an explicit text to a new Hire using the company comms system. She pretended to be interested and then reported him, with a very long thread as proof. Dude was married, with kids, a supervisor. Now: Divorced, kids hate him, works a low level job. Reply 5.2k
    via r/AskReddit

    "I knew a guy just like that. Had a really well paying job. Didn't do anything all day at said job. Always talked about how he was hot shit in high school, but he's now over 30 with a wife and 2 kids. Then there was this new hire at the job. A younger woman in her very early twenties. They had some extra marital encounters, but turned out he was a giant asshole (who would've thought from a guy that peaked in high school). They got into a spat at work, and she ran to the HR department and showed everyone the disturbing messages he has been leaving on her phone alongside some dick pics. Last I heard was he got fired, but still came back the next day and chilled in the lunch room all day. When the boss heard of this weird development, he called the police, but the guy was long gone before the police got there." said u/gnottydevil.

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  • 17
    Font - Massengill4theOrnery. 1d The numb nut that carved on the Coliseum Reply 4.5k
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  • 18
    Font - gaspronomib. 10d Saw a pilot without instrument rating take off into IMC conditions (instrument-meteorological conditions is a flight category that describes weather conditions that require pilots to fly primarily by instruments rather than use visual cues to maintain controlled flight). He had his whole family on board. Weather was closing in. He agreed that it was impossible to get home, but wanted to make it to a larger municipal airport so they wouldn't have to stay in a motel. The fu
    via r/AskReddit
  • 19
    Font - All told, it probably took fifteen minutes for this guy to make the worst- and last- decision of his life. This was over 30 years ago, but it's haunted me ever since- what could/should I have done differently that might have convinced him to not fly? I was a newbie pilot at the time, but even I knew it was a bad idea. There were at least three other pilots there that day. Did he feel ganged up on? Could we have appointed the most grizzled straight- shootin gravel-voiced veteran to take th
    via r/AskReddit

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