Life-Ruining Mistakes

March 6, 2024 | Jennifer McFarlane

Life-Ruining Mistakes


Everyone has made mistakes in life. No matter if it’s a minor mishap or a huge disaster, mistakes always serve as valuable learning experiences. However, mistakes can also be hilarious, cringey, and downright terrifying.


1. Wild Encounter

This girl I know was super tipsy. She had the brilliant idea of approaching a wild raccoon and petting it. BIG MISTAKE. The raccoon jumped and landed on her face, leaving her with horrible facial scarring that she never fully recovered from. 

She proceeded to get addicted to the painkillers she received from the doctors after the attack. Two years later, she succumbed to the destructive habit. She was a very beautiful, intelligent girl with a bright future ahead of her, totally ruined because she thought a raccoon in the park was cute.

Worst MistakePexels

2. Mr. Wrong

My former best friend started dating this lying lunatic. She hadn’t been in a long-term relationship for years at that point, and this loser showed up on a dating app. Within a week, he was living with her. It was a recipe for disaster.

All of her friends (there was a close-knit group of about eight women) and her family all kept pointing out inconsistencies and outright lies. I got in touch with his baby momma to find out their history and she was more generous than the court documents were to him.

Apparently, the baby momma had left her job and sold her house so she could go live in the work van she had bought this dude. They wound up homeless and pregnant in Florida with two cats and two dogs until her parents felt sorry for them, gave in, and helped them set up somewhere nearby. Before it all fell apart, of course.

Some examples of his lies are that he claimed to be a top-tier chef when he was really a dishwasher. He also claimed to know jujitsu and was a practiced MMA fighter. Nope. He also claimed to know how to build a bathroom because he was a tile guy. Again, nope. 

This villain took my friend, this wonderful woman, and turned her into a backwoods baby machine and he still isn’t working a job!

Worst MistakeShutterstock

3. One Slip-Up

It's a day I'll never forget. I had some nice plans to stay home and work on my truck that day, but a friend asked me to do some outdoor portraits of her so that she could send them to her husband in Afghanistan. I didn’t really want to do that, but she was a friend. 

I was a former professional photographer before deciding to go back to school, and since her new husband had just been deployed, it seemed like the right thing to do. We were hiking on a rim trail that skirted the south side of Rocky Canyon outside of Boise, Idaho when the worst happened.

A section of the trail collapsed and slid over the edge, taking me with it. I fell about 100 feet, bounced off a ledge, then fell another 150 feet or so and landed flat on my butt in a dry creek bed at the bottom of the canyon breaking my back in seven places along with four ribs. That day absolutely destroyed my life.

I was in my early 20s, an honor student at Boise State, and had just achieved my lifelong dream of living out west. That morning I was happy and had my whole life ahead of me. By that afternoon it was all stripped away. Now I require a wheelchair to get around. 

I am constantly in serious nerve pain, lonely, and miserable, and I haven’t left my house for anything other than to see a doctor since 2014 because of how incredibly painful it is to be up and about for more than a few minutes at a time. I wish to God that I had just told her no and stayed home to work on my truck that day!

Blurred Photo of Person Using Wheelchair moving in a hallwayMarcus Aurelius, Pexels

4. Prince Affluenza

I have a relative whose parents were multimillionaires. I've never seen a person crash and burn quite like him. They indoctrinated my relative with an alpha male complex while he was young, so he grew up believing he was extremely intelligent, powerful, and shouldn’t have to work due to his family’s success. 

We once argued and he ended up calling me a poor loser from a poor family, or something like that.His parents more or less supported this mentality. They believed he would be a leader because he was attractive, confident, and academically successful. Naturally, he started taking narcotics and steroids in high school. 

He also used to drive a Porsche, Mercedes and had all kinds of expensive things. He was very inconsiderate to everyone, including his own family, and was super vain. Then he went to some expensive college and got in trouble for harassing a girl—but he didn’t stop there. 

Once he flunked school, his parents continued to support him while he would disrespect them verbally and physically. He was becoming dangerous, and his parents were probably afraid of him. Eventually, his parents divorced (probably because of him) and they cut him off financially. 

After that, he got locked up and when he got out, he had to resort to couch surfing off other relatives for a while. During this time, he gained a lot of weight. And, because of his extremely erratic behavior, his parents tried to save face by claiming that he had a mental disorder. But I know the truth

Most of his behavior was learned and enabled by his upbringing. He once had everything in the world going for him, but now, he has a bad record and physical and mental issues. The lesson I learned from this is to never spoil a child that you care about. 

Children are malleable, like soft clay, when they’re young. But as a child grows older, they harden into the shape they were cast and molded into. They can’t be easily changed after a certain point.

Worst MistakeShutterstock

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5. Love Can’t Wait

A friend of mine messed up so terribly—I'll never forget it. She left college in our final semester (she had a full ride, scholarship, cheap and safe apartment, and a great job) to move cross-country for some boy she'd been chasing since middle school. I worked in financial aid at our college and sat her down to explain how idiotic her decision was. 

She only had four months left and out-of-state charges much higher tuition, she would lose all her state-specific aid, and would lose a lot of credits. Her reaction was brutal. She called me jealous and cut me off, saying the boy promised he would take care of everything. I was the only one who was honest with her. 

It took her three years to graduate on the West Coast. She took out tens of thousands of dollars of loans. She lost almost a third of her credits. Her GPA tanked and, of course, the boyfriend slowly iced her out once he had her there. They broke up a year later. This was 12 years ago. Unfortunately, she never really landed on her feet. 

She moved from couch to couch, then back in with family, then had a mental breakdown. Only just NOW that she has a stable job. Before this, she was only able to get gig work. To think that she blew up everything she had over some guy that wasn't worth the plane ticket, when she could have just waited FOUR MONTHS, is still mind-boggling to me.

Worst MistakePexels

6. Next Level Delusional

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. But that wasn't even the cringiest part. As it actually turned out, she was just being friendly and chatting to him. No relationship, no mutual decision to be together, nothing. 

He misunderstood polite friendliness for flirting, and destroyed his own family for it.

Mary Robinson, The English Sappho factsShutterstock

7. Machine Washable

All through public school, my cousinwas a snob who looked down on everyone. She was super stylish but struggled academically. We graduated in 2014. We both went to colleges (not the same one). She got a job at a bar, stayed out late partying. But then her behavior took an even more alarming turn.

Her boyfriend told her she didn’t need to complete college, so she just stopped showing up. She didn’t drop out, she just stopped showing up. So, she completely flunked out. Our families lived hours away from her college at the time. Her family went to move her back home. My cousin’s mom noticed a pile of clothes in the corner. 

The mom said, “What’s that, your laundry? Pack it and we’ll wash it when we get home later”. I still can’t believe what she said next. My cousin (I kid you not) replied, “You can wash those”? It turns out, she’d been throwing away clothes instead of washing them. 

She claimed she didn’t know she could, yet she washed her undergarments and bras without a hitch. She’s now at home with her family and has started doing more chores to show an increase in responsibility. She still tries to throw clothes away, citing that she didn’t know they could be washed and reused. 

Makes me wonder what she thought all those years before college, before she left home. She wore some of the same outfits repeatedly—she had to have known they could be washed.

Worst MistakePexels

8. Royconomics

I worked once with a man named Roy. Roy had "theories" about how to live life. We called it “Royconomics”. One day, he turned to me and the other member of the crew. He asked, "You boys wanna know how you get nice things?"

I was like, "Whaat?" He went on, "You go to the store and you finance everything. New furniture, new appliances, televisions, stereos, everything. Then, you don't make any payments, and you don't show up for your court date. They'll end up garnishing your wages, but they take way less than the payments would have been!" Somehow his advice got even worse.

Then, about a week later, "You boys wanna know how you buy a house? You apply for every credit card you can possibly get, you take out your entire balance in cash from all of them, and you use that for your down payment. Then, you don't make any payments, and you don't show up for your court date".

Worst MistakePexels

9. Lucky Bird

This the story of my biggest mistake. To be honest, I still get bad dreams about it. When I was 16, my first job was at PetSmart. One night, I was cleaning out the bird/small animal habitat. The procedure was to haul a ShopVac into the little room and vacuum up the spilled bird food/seeds/litter. Easy peasy. 

So, I'm cleaning out the cage with the cockatiels in it when one of them decides to investigate the loud sucking machine. FWOOMP. The bird is gone, stuck in the tube. I use a box cutter to rip the hose in half so I can get him out. I’m distraught. The bird is missing feathers and bleeding. 

I run to my boss crying, "IJUSTSUCKEDACOCKATIELUPINTHESHOPVACHESGOINGTODIEIAMAHORRIBLEPERSON". He takes one look at me, then the bird, and starts laughing.

I ended up driving him to another PetSmart that had a veterinarian in it as part of the store. The vet laughs and gives the bird some fluids. My co-workers named the little guy Hoover and he lived in quarantine in the back of the store for months until his feathers came back. Then we put him back out for sale.

Their Biggest Workplace Mistakes factsPixabay

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10. What Are The Odds?

It was a few years back when the Mega Million Lotto had reached its highest in history, more than a billion dollars. Everyone was buying tickets. At the time, I worked at a 7/11 in Maryland and a middle-aged woman came in. I'll never forget what she placed in front of me: a bag full of hundred-dollar bills. 

She confidently placed the bag on the counter, looked at my co-worker, and said “I’ll take 8,665 lotto tickets”. At the time, a Mega Million ticket cost $2.06. So, doing some quick math on my phone, I knew she spent $17,849. Also, it was annoying because we ran out of print ticket paper so no one else could buy a ticket for three days.

Long story short, she didn’t win. I’ve never been well off personally, but I feel like anyone besides the wealthy losing $17,000 is a lot of money.

Worst MistakeShutterstock

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11. Big Regret

My friend did something so idiotic. She gave up her full-ride scholarship to play volleyball out of state because her boyfriend wasn't gonna be able to go to college with her—but there was something that she didn’t know

Not only was he cheating on her, he dumped her not even a year after she gave up her scholarship. Now, she lives in a constant “what if” because a couple of her other friends have started to play pro volleyball around the world.

Worst MistakePexels

12. My Strange Obsession

I knew a guy who abandoned his wife and child for the My Little Pony fandom. Yes, you read that correctly. It was during the early days (early 2012, he was in his early 30s at the time) and he was convinced he could make it as a fandom artist. But here's what the problem was...

His art was...not good. But that would be okay if he wasn't set against anything that could help him improve. It got to the point where he quit his job in radio to focus on trying to make it as a fandom artist. He started trying to sell at a few cons and did very poorly. 

Eventually, his wife, who was a British ex-pat with very wealthy parents, was offered a lucrative publishing deal in Britain, so her parents said they would sponsor him and support them moving to the UK. He had a full ride and a very good-paying job lined up at his in-law’s company. He would have wanted for nothing.

He said “no” because there were no Pony cons in the UK. I am not kidding. So, his wife moved back to the UK with his daughter. His wife tried to make it work, and tried getting him to come to the UK to visit her and his daughter. He had absolutely zero interest in doing so. He was 100% focused on MLP art.

Eventually, his wife divorced him. Obviously. He has not spoken to his daughter or his ex-wife in years.

Today, the My Little Pony fandom is relatively over and done with, but he's desperately clinging on to it. He argues with anyone who tells him that it just isn't very popular anymore. He has lost all semblance of sanity. Thankfully his wife has remarried, and his daughter is doing well. I'd honestly be surprised if his daughter even remembers him at this point.

Worst MistakePexels

13. Sad Song

My sister was a musical savant on the piano. She turned down a full ride to Juilliard so she could go on a Mormon mission in Los Angeles. Three months into it, disaster struck.

She got hit by a car which broke both of her legs. She ended up living back at home and faced years of depression. She felt guilty because she thought she'd "failed God". She got married, had a kid—but then it got worse.

She found out her husband was a creep and extricated herself. Now, she’s a single mom with no skills, no safety net. I think it's one of the most breathtakingly stupid decisions anyone in our family has ever made.

Embarrassing momentsShutterstock

14. Vote For Me

Without any proper planning, my brother decided to run for public office. He had no leadership qualifications, background in the position, or support from anyone in the community. He took out a $10K personal loan to finance the run. He lost badly, coming in last. 

It took him years to pay back the loan and refill his savings, which he drained to pay for signage and flyers—but there was a hilarious twist. The printer misspelled his name on every item, so any remnant is a harsh reminder of how badly things went.

Mortifying Mess-UpsPexels

15. Let It Ride

Oh boy, this is why I never gamble. I literally watched a gentleman, who happened to be plastered, throw $2,000 on a single roulette number, lose it, went to withdraw $5,000 more, put it on the same number, lose it, then stare blankly at the table. All while on a cruise ship. Then, I went over to the ship’s bar and ordered myself a drink and it was wonderful.

Biggest secrets from parentsUnsplash

16. Investment Opportunity

My friend retired with a full pension 15 years ago. At the time, he kept bragging about how he was starting a new business with some random guy he knew. My friend legit said, "He's the idea guy. I have the savings and the good credit score".

So, my friend hurries up and takes out a huge bank loan and purchases a bunch of expensive equipment. He had no idea what he was getting into. The venture completely flopped half a year later. Even worse, his so-called "partner" disappeared and took all of the expensive equipment.

So now, my friend, who should be enjoying his golden years, will be working a retail job until he drops.

Worst MistakeShutterstock

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17. No, Don’t Bother Listening To Me

My best friend has been married to his wife for 18 years, but he recently left her to be with my ex-girlfriend. I did try to warn him about the fact that she cheated on her previous boyfriend with another guy and myself and she seduced him, a married man, and cheated on me with him. She lied to everyone, including my best friend, to hide things from him.

She manipulates, she plays the victim, and rejects every mistake she made, blaming others. I know she told him "her truth" yet he still repeats that "the last year was hard on her and he will not blame her for past mistakes". She was telling me less than two months ago that my best friend was a manipulative, harassing, narcissist.

I can see the future already. I know he will be in great trouble when she finally leaves him after cheating on him, all while saying anything to play victim. I can easily see that it’s going to be the biggest mistake he will ever make. I did warn him. But let's pray they will stay in love forever and live happily ever after.

Worst MistakeShutterstock18. Big Fish, Small Pond

I watched two guys in my small town think that they were the "big man on campus". It ended up destroying them both. Over time, they realized they weren't the biggest, the fastest, the best, and people weren't going to just give them everything they wanted just because they thought they deserved it. Their fates were truly disturving.

One of the guys drank himself to the grave and the other one is one-third of his size in high school and looks totally down and out.

Worst MistakeShutterstock

19. Dumpster Fire

My friend decided she wanted to move out, because living at her mom’s house when she was nearly 30 was for losers. But it wasn't that simple. She had two kids under age five and had just broken up with the abusive father. She worked a slightly above minimum wage job. 

She found an apartment where rent alone would be 80% of her take-home pay. No amount of shouting down the telephone how stupid that would be convinced her it was a bad idea. So, she moves in, but struggles to find daycare, driving against traffic to drop them off at her mom’s. 

She has bills to pay and is underwater every single month. She asks the  baby daddy to move in. However, he's the absolute worst. To make things even messier, she starts sleeping with her married boss. When I asked her why not just find a random guy on Tinder, she said it was full of weirdos and creeps...as though her married boss wasn't!

Nasty FamiliesPexels

20. L is for Loser

My ex-husband truly messed up. I’m not even old, I’m 25. But he ran off to hang out with an 18-year-old. Which was honestly fine. My life has been easier as a single parent. However, he recently sent me a random text message that made me shake my head.

I’m not even stopping him from seeing the kids. Honestly, the amount of drama and heartache he brings on himself. But, of course, I get blamed by him because I want him to buy diapers for the kids and this means I’m trying to destroy his life by asking for child support.

Worst MistakeShutterstock

21. Get Out The Popcorn

I’ve been watching a former buddy/roommate of mine ruin his life in real time for the last few months now. We’re both in our mid-20s. He got a bipolar addict pregnant recently. He wasn’t even dating her, just a rebound thing, but she wants to keep it. I don't think he realizes how serious this is.

He’s pretty passive and it’s clear he’s just letting it happen rather than actively choosing that life of parenting with her. He tends to get involved with disturbed women and never stands up for himself until it’s “too little, too late”. 

Unfortunately, this time, that’s not gonna happen until after that kid comes along so, right now, I’m just eating my popcorn and bracing for all the drama that’s gonna hit my friend group over the next few months and years.

Worst MistakeShutterstock

22. There's No Future Here

My biggest mistake was becoming a stay-at-home. Now, don't get me wrong, I love my kids. I really enjoyed the time I spent with them, but unfortunately, I failed to plan for the future. My marriage is loveless and I'm so unhappy. I have no Social Security, no work experience, and no 401(k)-type of retirement. 

It feels like my options are work until I die or stay in an unhappy relationship.

A sad woman grocery shoppingDrazen, Adobe Stock

23. Life Comes At You Pretty Fast

One of my friends in undergrad had a 4.0 GPA our junior year, and was already looking at vet schools, was on a full ride, was absolutely beautiful, funny, smart, would be the first in her family to get a degree. Then, she got pregnant from a guy she had known for two months and decided to keep the baby. 

Unfortunately, he was the worst guy ever. He treated her terribly. BUT at least he had a high-paying job (oil driller). Well, he gets himself fired three months before their baby is born. She took him in and waited on him hand and foot while heavily pregnant and immediately after having the baby. 

She dropped out of school to marry him, moved back home to her tiny town, and reaches out every few months to try to get me involved in a different pyramid scheme.

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24. This Floorplan Is Nicer Anyway

When my parents built their house, the guy that staked out their foundation did so from the wrong blueprint. It was totally the wrong house. That guy lost his job, but before they fired him, the company tried to get my father to change his mind and get a completely different house than the one he bought because of the mistake.

When my dad said, "no way", the housing developer company tried to get him to build on a different lot. When he said "no way" to that, they tried to get him to eat the cost of removing the wrong foundation and having the site prepared for a second foundation. Of course, he said “no way” to that too. 

There was a huge fight over it with my parents. But they didn't give up. Lawyers were called, my dad nearly had a heart attack. The end result was that they got the house they wanted but it took an extra-long time.

Oversharer factsShutterstock

25. Imaginary Wife

I watched a friend let go of his fiancée just as their wedding date was approaching. His reason why was absurd. Somehow, he developed this mental concept of what a wife “should” be like and she didn’t match up to that concept. He lives in deep regret now as she ended up getting married to his friend and they’re living happily ever after whilst he has never found anyone else.

Worst MistakePexels

26. Trapped Inside

The biggest mistake I’ve witnessed is watching friends and family remain in an obvious cult that controls nearly every aspect of their lives, from their diet to their time, to everyday choices, to their income, to their underwear. 

Speaking as one who left the cult, it's mind-boggling that anyone stays, especially with all the historical records and even the cult's own records that effectively renders the whole religion false. Like, so false it's not even debatable.

I can't wait to see my loved ones finally living their own lives and finding real happiness. The cult is even relaxing some hard, strict rules to prevent members from leaving as much as they can, but there's only so far they can go before they start contradicting core beliefs. 

Even though I've been free of it for years, it's still a struggle. You have to completely de-program the way you think and live.

Middle Of Nowhere FactsShutterstock

27. Never Do Business With Family

In 2005, my mom refinanced her house to take out a second mortgage and invest in some guy's house-flipping business at the recommendation of her cousin who vouched for the guy. Yeah, probably the worst mistake of her life. Turns out the guy was a scammer and then, of course, the housing bubble burst in 2007. 

She nearly lost the house and is still paying off the debt to this day. She was struggling with substance use already before this but, after this encounter, she was gone. She has has no license, and no job. My siblings and I went through hard times. Her cousin convinced his parents to invest too, and they lost most of their retirement. 

Most of the family doesn't talk to him anymore.

Worst Dates FactsPikist

28. Is That Any Way To Say Thanks?

I watched my cousin get married to a guy who needed a US green card. She'd only known him for four months. Everyone told her he was a snake, based on his behavior, but she insisted they were in love. A baby soon came along, then, once he thought she was trapped, things took a dark turn.

He started treating her terribly. What's worse is that she left him for a while and then went back, claiming he had changed. NOPE. He started getting physical with her all over again. So, she made the same mistake twice. They're now divorced. If someone hits you once, they'll hit you again.

Wedding DramaPexels

29. Lowered Expectations

My disabled brother fell for an internet scam—and it was seriously heartbreaking. He met a lady online. She lived on a different continent, but he was certain she was the love of his life. Spent over a year chatting and emailing. He helped her with money too. Very fishy stuff, but he refused to listen to my skepticism. 

Finally, he saved up enough to visit her. When he returned only a couple days later, I knew it went wrong. He refused to confess what actually happened. Went to his grave without talking about it.

Worst MistakePexels

30. Keep It Shut

A close family member and their spouse decided to open their marriage to outsiders, which is not always a mistake but, in this case, it was awful and quickly descended into chaos, cheating, maltreatment, and separation. They are STILL not through with this messy divorce—and it's been a whopping five years. 

It’s seriously the worst, meanest divorce I’ve ever seen, and the situation has ruined four lives so far.

Wedding ruinedShutterstock

31. What Were You Thinking?

We have family friends, a couple married for 30 plus years with three daughters between 24-30. The whole family is very social, lots of social gatherings at their house. The husband/father was a general manager at a popular local brewery and restaurant. He seemed nice enough, but he messed up terribly.

He decided to have an affair with an employee who is absolutely crazy. This horrible decision ended up breaking up this man’s entire marriage and family. He also lost his job at the restaurant and now he’s in this busted-up relationship with this crazy chick who beats on him. This has all gone down in the last year. 

It’s been absolutely wild and heartbreaking to witness. And to steer clear of!

Worst MistakePexels

32. Trainwreck

Just watched my cousin move out for the fifth time with no plan, nowhere to go, and hanging out with manipulative people because they want her disability check. When my grandma tried to help, she was super rude to her. 

She also got kicked out of one of the hardest community centers to get placed in. Now she’s sleeping in one of the most dangerous parks in town. I’m gonna try to talk to her tonight but honestly not sure what to do as this has been continuous for months.

Worst MistakePexels

33. Paperback Writer

A woman at my job quit to pursue writing because "she liked to tell stories". There were just one or two problems. She never had written anything and didn't do any research on how to make a living as a writer. I tried to suggest to her that maybe she could work part-time to at least have some income until she can live off writing.

She had two kids and, from what I understood, her husband didn't earn much. And this lady was utterly oblivious to the ways of the world. She said money wouldn't be an issue because "she was going to specialize in writing best sellers". Biggest facepalm I ever had.

Virginia Hall FactsShutterstock

34. Success Story

My best friend met a woman who was a refugee. They were about to break up, but she manipulated him into sleeping with her a few more times. She got pregnant so he married her. He renovated his parents' former home so they could live there, but she said it was too ugly and demanded an expensive condominium.

This woman did not want to get a job, so my friend supported her. Then, she arranged to bring over her family from overseas—her mother, father, and seven siblings who my friend became responsible for. They also had four more children together. My friend was fairly certain that at least one of the children was not his child. But that's not the end of the story.

Fast forward ten years and my friend has had a complete mental breakdown. He is living as a homeless man, penniless, and cannot see any of his children. His ex-wife is a well-to-do local semi-celebrity. She joined some kind of foundation for immigrant women's rights and because she was attractive and charismatic, she became a kind of spokeswoman for the group, appearing on the news and local TV frequently.

Ex-Employers’ Hidden SecretsPexels

35. Ignorance Is Bliss

This story happened to me. When I was 18, I worked at a bagel shop. I was fairly new working there when a customer came in and ordered a bagel with, what I heard as, "lots of cream cheese”. So, I toasted a bagel and lobbed a large amount of cream cheese on it. He paid, and left. 

A few minutes later, he came back and complained, with what I heard as, "I ordered LOTS of cream cheese!" I thought that this man was insane. How much cream cheese can one person want!?! So, I lobbed on two heaping ice cream scoops of cream cheese onto the bagel, packed it up, and sent him on his way. 

He came back, irate, yelling "I ordered LOTS of cream cheese!! What is the problem?" I responded, stating I gave him lots of cream cheese. I couldn't fathom eating any MORE cream cheese than what I'd given him. Two HUGE ice cream scoops full. That's when he suddenly SMILED. It clicked. He explained, "I ordered LOX and cream cheese! LOX! Salmon!"

Worst MistakeShutterstock

36. Get Here ASAP

Many, many years ago I worked with this dude at McDonald's here in Ohio. We were work friends, I guess you'd say. He comes in one day and tells us all that he's quitting, that this was his last day. 

So, I asked him, "Why the heck are you doing this?" I couldn't believe his response. He tells us that he met a girl on the internet a few days prior and she convinced him to drop everything he had and move in with her up in Providence, RI. We try to explain to him all the reasons he shouldn't go but, of course, he doesn't wanna hear it.

When we ask him how he was even going to get up there, he says he's using a credit card to rent a car, then after he gets the car, he's going to cancel the card so he doesn't get charged for it. He's essentially planning on trying to plunder a car. 

We tried to explain to him that that wasn't going to work either and was probably not allowed, and he ignored that as well. We never saw or heard from him again.

Worst MistakePexels

37. Life Choices

When I met my boss, he was a bit of a wunderkind in our Division, having come in at a young age and moved up the ladder. Younger than me, he had already become a manager and, while I had no interest in following his path, he always seemed to be zooming through life. 

He'd check his credit score constantly at work but, at the same time, did overwhelmingly dumb things like leasing an expensive motorcycle and car simultaneously. We finally parted ways when our location was shuttered, and we split apart to different locations. 

He had traded in both of his vehicles for a much more modest car, had met some girl with SIX children who were all from different fathers, and was planning on marrying her. After a MONTH. Now, I have nothing wrong with single mothers as I was raised by one. But this woman was not hard working. 

Fast-forward, he marries the girl, has a kid with her almost instantly, lets her stay at home while he works. She ends up getting him hooked on illicit substances and cheats on him repeatedly. It all came to a head in a chilling way. He wanted to end it all, so he ingested a buch of pills and got behind the wheel.

He drove his car the wrong way through traffic, and crashed in a hospital parking. It was so bad, his heart stopped. They were able to resuscitate him, thankfully. After all that? He went back to her. That is the worst mistake I've seen someone make.

Woke Up In A HospitalWikimedia Commons

38. Never Go Back To An Ex

I am somebody who has always been extremely careful when it comes to relationships. A couple of years after my husband passed, an ex from years ago reached out, and we ended up reconnecting. Things went well, so we moved in together. He'd told me he was divorced. However, only months later, his sister contacted me.

She told me that he was still married. I confronted him about it, and he admitted the whole thing. However, he also said that he and his wife had been separated for many years—he just couldn't divorce her because he didn't want to hurt HER feelings. I felt so betrayed and humiliated.

Get That Dark Secret Off Your ChestPexels

39. What A Fool

There was this guy at my high school that wasn't too bright and was mostly harmless but about halfway through, he decided he was gonna be a thug. One day, he goes into a class of first years when their teacher wasn't there, and robs all their electronics, cash and valuables at knifepoint without covering his face. 

Before he left, he gave them his real name saying, "And you better not tell them it was me, Jim Conrad, that took all your stuff". He then proceeded to leave the school grounds with all the lifted stuff. But he decided against stashing it off campus.

He came back with all the plundered stuff in his backpack and went back to spy on the class with his backpack full of loot while authorities were taking statements to make sure the students weren't ratting him out. Of course, all the kids did rat him out.

When Jim hears his name mentioned, he does the most idiotic thing possible. He storms back into the classroom proclaiming he's going to hurt them if they don't take back the accusations saying he did it. Meanwhile, the authorities are still inside the room, and he has all the loot on his person. He was seized and expelled from school. 

Everyone in our year group just face-palmed.

Teachers Got Fired FactsShutterstock

40. On Fire

My roommate was a real piece of work. I heard panicked shouting from the kitchen, so I rushed in to see what was happening and see him holding a burning paper towel in his hand, waving it around and holding it so the flames were climbing towards his hand. I told him to drop it and quickly stomp it out. When I heard the story, I was stunned. 

It turns out, he had turned on our gas stove with the paper towel nearby (for some reason). I don't know if you can be stupider than screaming about something about to burn you and then doing absolutely nothing to stop it. I realize it was part of his panic response, but what if I had not come into the kitchen at that moment?

Search Histories factsShutterstock

41. One Small Thing

A guy I know worked in windows and doors. He spent years developing an excellent reputation for working on high-end homes, working with the architects on the front end, clients and contractors on the back end. It was a sweet deal for a guy in his late 20s. The money was good and business was booming. 

Some of the jobs were big and needed serious project management so he needed to be on site a few times a week. In this particular job, everything was custom; paint, wood, mill work, glass, hardware. The total job cost was $750,000+ and he was acting as an independent contractor supplying the material.

For nine months, every detail was planned. It took two whole days to go over the specs line-by-line. The client and contractor signed off on every item. Finally, with the deposit on the materials, he initiated the order. Six months later, everything was in and the contractor was ready. Delivery to the muddy site was not easy. 

It took three trips over five days just to get the windows delivered. It all looked good. The contractor signed off and all he needed to do was go home and wait for the final check. The phone rings. His blood runs cold. It was the interior designer saying, "These aren't the right color". The consequeces were devastating.

He has to eat the windows and eat the cost of sending a crew out and replacing the windows with the correct ones, eat everything. He went out of business at the end and went back to college.

Plot TwistsShutterstock

42. Grand Theft Auto

Buddy used to work at a car rental place. His job was to clean the cars, prepare them for customers, and do inspections before renters took off with them. One day, he was in the lot parking a cleaned truck before heading back into the office. 

It wasn't uncommon for people to approach with their rental papers and ask for the keys, so as he was walking back, a couple of older grimy looking guys walked up to him. The one guy says, "Hey, we're all done inside and the lady said that truck is ours". That's when Buddy made a terrible mistake.

Without even asking a question, he hands over the keys and says, "OK great, here ya go!" Then, he returns to the office without a care in the world and sees his boss. She asked if he saw those two guys out in the lot and he says, "The guys who rented the truck? Yep".

She looks at him with her jaw on the floor and says, "NNNNnnnoooooooooooo". She then immediately calls 9-1-1 to tell them a truck was stolen from the lot. Weeks go by and eventually the truck turns up out in the middle of nowhere completely trashed. Buddy then had to go to the station to pick out the guy he gave the keys to out of a photo lineup.

Ruined Jerk's Day FactsShutterstock

43. The World, Ontime

My friend and I worked in a mailroom right out of college for a fairly large company. Oftentimes, we had “Overnight” and “Next Day AM” packages that had to get there or, apparently, the world would explode. He was responsible for getting these to the drop boxes before pick-up time, which means he had to take them when he left work and drop them off.

Well, one Friday, he had one of these urgent letters. He left work and completely forgot about it. It sat in his car all weekend. When he got to work the next Monday, the CFO and several upper management were literally freaking out because the letter didn’t arrive. The contents of that blasted letter explained why.

Apparently, it was a half-million dollar check that this company was waiting for or they were going to take some kind of court action or something.

Dead Have Their Secrets factsPxHere

44. A Fine Performance

I used to work at Chuck E Cheese and saw a fellow employee take a pizza from the kitchen to the customer. At the time, it was extremely busy and there were little devils running everywhere and this lady was at the far end of the restaurant, so he had to zigzag through the games to get to her. 

After successfully maneuvering through a bunch of games and small children, he came within 10 feet of her table. Home free, right? Wrong.  Turns out there was a two-year-old kid crawling right in front. He tripped on the kid, the pizza went flying and hit another kid, and both of the kids were crying because he stepped on one and nailed the other with pizza. 

And before you think this can't get any worse, he then had to deal with the parents. That part alone still makes me shudder to this day. After yelling at him, they pressure the manager to fire him. But thankfully, karma was on his side.

The manager was a cool guy so he said no, but he pulled the employee aside and told him he would have to pretend to go berserk on him to make the parents happy. He did and it was the finest acting I have ever seen a non-actor pull off.

Ex-Employers’ Hidden SecretsPexels

45. As Loyal As A Golden Retriever

My dad quit an $80,000-a-year job in solidarity with his department after the department was dissolved and they were all given notice. My dad would have still had a job at that same salary but he felt loyal to his work family, so he gave notice. I wonder if regrets doing that.

My parents used up all their savings, lost their house, and went into bankruptcy, I guess for the principle of the thing?

Worst MistakePexels

46. Hollywood Or Bust

A friend of mine wanted to go to LA and "make it big" in acting. He quit his job, sold all of his possessions, and hit the road with no real plan. We are in Canada so at the border, he was asked the normal questions border guards ask. When they realized his intent was to go there to work and live without any kind of work visa, it did not go well for him. 

He did not get into America and had to move back in with his parents.

Overheard messedPexels

47. Wowwww

I seriously can’t believe I had to watch this happen. A family member got tricked into adopting three children because her "friend" was dying of Stage 4 cancer. Miraculously, after the adoptions went through, the "friend" started to get better and bailed on her family by moving to another country. I think this kind of ruined her life.

Now my family member is a single stepmother with three kids that hate her.

Questionable Paternity factsShutterstock

48. All For Nothing

My co-worker stayed with her boyfriend who landed behind bars for taking another person’s life. He served 20 years. He got out and she rented a house with him, financed a car and motorcycle, and got two pit bulls. She paid for EVERYTHING. She had also spent the last 20 years caring for his son from a previous relationship. I guess love really is blind...

Two months after release, he knocks up his side chick and leaves my co-worker. We all tried to warn her. She got stuck with all the debt and fiddled away 20 years of her life.

Crazy ExesShutterstock

49. No Thanks, I’m Done

I know a guy who just one day decided he didn't want to be married or be a father to his two kids anymore. Didn’t care about custody, just didn't want any responsibility. He didn't have a mistress (as far as anyone knew), he didn't move far away, he didn't change jobs, he just seemed to not want any responsibility anymore. Well, he didn’t see what was about to happen to him. 

He quickly found out that people are kinda judgmental about voluntarily abandoning your kids. People at work who knew him stopped talking to him, his entire family shunned him after yelling at him for being a lousy fella, and anyone that might have been a friend didn't want anything to do with him anymore. 

His now ex-wife rightly took him to the cleaners for full child support, alimony, etc.

Lawyers Screwed factsShutterstock

50. What Am I Supposed To Do?

I went on a date with this lady I met online. We didn’t hit it off, so that was that. About a week later, she calls saying she needs my help since I seemed like a kind person, and she needs someone who none of her family or friends knows. Hesitantly, I ask her to explain. Her story made my jaw DROP.

So apparently, her grandma passed shortly after our date, and it unleashed a storm of drama in her family. She spiraled emotionally. It was in that state that she decided she needed to get away and took a trip to Las Vegas where she proceeded to lose every cent to her name, which was around $50,000. 

She even sold her plane ticket home and lost that. The only thing she had left was her phone. She had managed to hitchhike from Vegas to Victorville and that is when she called me.

Worst MistakePexels

51. Suspicious Much?

I dated a woman for five years. She came from a broken family and the consequences were devastating. She just couldn't accept the fact that not all men are cheaters. From sharing passwords to sending her live locations, I still couldn't earn her trust. I asked if marriage would put her mind to ease. She said “yes”. 

So, I proposed but was told to “try again” because she wanted it to be grand and proper. Saved up for six months, booked the venue, and started calling her friends to inform them. Five calls in, and the guy on the other end drops a bombshell on me.

He says, "Buddy, I like you so I'm telling you this. She has been seeing another dude for three months now and they are hanging out every day after work". Today, she’s still single, always complaining about how men don’t do right by her.

Courtroom Dramas BehemothShutterstock

52. Don’t Tell Dad

My mom got herself into a bit of debt when I was young. She didn’t tell my dad about it and started hiding the mail and never answered the phone. It kept getting worse and worse. It got to a point where she was also hiding his mail. Before she’d go out, she’d tell us to make sure we throw any letters away if they came in the mail.

Of course, we didn’t know the reason why, but she’d throw a hissy fit if she found that we hadn’t. My dad kept asking us where the mail was. For a while I just said I don’t know, not wanting to upset mom. Eventually, it reached boiling point. Dad found bills, loads of them. A big argument ensued. She owed a lot. 

They’re still together, but if I’m honest, things have never really been the same since.

Dumbest Person FactsShutterstock

53. Is That All There Is?

A middle-aged guy I know was living the dream in a $15 million house, multiple boats, owned a very successful business, had a beautiful wife and kids. Then he threw it all away in an instant. I don't know all the details, but he started an affair with a younger girl, got caught with an illicit, and got addicted to pills. 

It all came crashing down relatively fast. He's still alive and climbing his way back now, but he lost his family, house, possessions, and his business.

Everyone Makes Mistakes At Work, But These Are UnforgettablePexels


Sources: Reddit, Quora, Buzzfeed


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