The WORST Mistakes

November 10, 2023 | Jennifer McFarlane

The WORST 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, they can also be hilarious, cringey, and downright terrifying.


1. Wild Encounter

I am acquainted with a young lady who once—while very tipsy—decided to stroke a wild raccoon. Unpredictably, the raccoon sprang up and attacked her, leaving her with brutal facial wounds that would never fully heal. The consequences were devastating.

She got addicted to the pain meds. This harmful obsession eventually claimed her life after a couple of years. She was an exceptionally beautiful and smart girl, with a promising future—ALL squandered because she pet an adorable animal.

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2. Mr. Wrong

My former best friend began seeing someone I'd generously describe as untrustworthy. She hadn't been in a committed relationship for a while and suddenly, she met this guy on a dating app. In no less than a week, he moved in with her. 

Her friends, a tight group of about eight women, and her family couldn't help but notice the inconsistencies and fabrications in his tales. I reached out to the mother of his child to learn more about their past, and let's just say, the reality was less flattering than the version he told.

It turns out that his ex-girlfriend had quit her job and sold her home to live in a work van she purchased for him. They ended up homeless, expecting a baby in Florida, surviving with two cats and two dogs until her parents took pity. They helped them settle somewhere only to have everything fall apart later.

Now, about his tall tales. He had led my friend to believe that he was a top chef whereas, in truth, he was a dishwasher. He boasted about being an experienced MMA fighter and having knowledge of jujitsu. Both lies. He even made us believe he knew how to construct a bathroom owing to expertise as a tile guy. 

Sadly, that too, was a false claim. And the worst part is, he transformed my friend, an amazing woman, into a stay-at-home mom while he, to this day, refuses to work.

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3. Prince Affluenza

I have a cousin who was born into wealth—we're talking millions of dollars. From an early age, he was conditioned to see himself as superior in intellect and power, a sort of "alpha male". He was also led to believe, due to the affluence of his family, that he shouldn't have to work. 

Once, we got into a spat and he referred to me as a "loser coming from a broke background" or something in that vein. His parents fuelled this mindset. They were under the impression that their son, being good-looking, brimming with confidence, and on top of his academics, would naturally evolve into a leader. 

He began experimenting with substances and steroids during his high school days. This wasn't a boy who found contentment in simplicity—he drove a Porsche and a Mercedes, owned a bunch of luxury items, and showed little regard for anyone, including his own family. His vanity knew no bounds. 

His next stage was an upscale college where he was reprimanded for mistreating a girl—oh, but that wasn't all. After failing in school, he continued to berate and physically disrespect his parents, who still provided for him. This was turning into a dangerous situation and likely filled his parents with fear. 

Eventually, they split up, which might have been instigated by his behavior, and cut him off financially. He later ended up behind bars and upon release, had to rely on crashing with relatives for a bit. Around this time, he put on an unhealthy amount of weight. With his increasingly volatile behavior, his parents attempted to explain it away as a mental illness. However, I knew better. 

His actions mostly stemmed from the environment he was raised in. The boy who had every advantage in life, now has a record and is dealing with various physical and mental issues.

The profound lesson I've gathered from his life story is to refrain from spoiling those you truly care for. Young children are super malleable, but once they reach adulthood, they'll be stuck in their ways.

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4. Love Can’t Wait

A buddy of mine decided to leave college in our final semester. She had a full-ride scholarship, a cheap apartment, and even a great job right on campus. However, she made a foolish decision. She decided to drop everything and move across the country for a boy she had been pining after since middle school. 

At the time, I was working in the financial aid department at our college. I sat down with her to express my concerns about her decision and presented her with some hard truths. She was only one semester, just four months, away from wrapping up her college education. 

Moreover, studying out-of-state meant higher tuition fees, losing her state-specific aid, and the potential loss of numerous credits she had worked hard for. Her response to my worries was harsh and dismissive. She accused me of being jealous and stopped talking to me altogether. According to her, the boy had promised to take care of everything. 

I was the only one in our group who voiced my concerns about her choice. She ended up taking three whole years to graduate once she moved to the West Coast, burdened herself with loans to the tune of tens of thousands of dollars, lost almost a third of her hard-earned credits, and her GPA plummeted. 

Unsurprisingly, the boy gradually distanced himself from her once she moved in with him and they split a year later. Fast forward twelve years, she has struggled to put her life back together since the fallout. She lived a nomadic life, moving from one friend's couch to another's, before ending up moving back in with her family. 

Unfortunately, she also suffered from a mental breakdown during this turbulent period. She only recently managed to secure a stable job after years of piecing together income through gig work. 

The thought that she decided impulsively to trade all the great opportunities she had for a boy who turned out to be not worth the plane ticket, especially when she only had to wait for another four months to finish her education, still leaves me dumbfounded to this day.

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5. Next Level Delusional

My good friend abandoned his wife and two kids, wrongly assuming that he was having an affair with a woman he met at the gym. The twist of the tale is that the woman was merely being sociable and considerate. There was no romance, no mutual agreement to be a couple—nothing of that sort. He mistook simple courtesy for flirtation and ended up shattering his family.

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6. Machine Washable

My cousin. Throughout our schooling years, she carried an air of superiority, looking down on everyone around her. She was always dressed to the nines but academically, things were a bit shaky. The year of our graduation was 2014, after which we both embarked on our college journeys, attending different institutions. 

My cousin took up a job at a local bar and spent her nights partying. Her boyfriend convinced her that she didn't need a college degree, and so she quit. She didn't officially withdraw; she just stopped attending, resulting in her flunking out.

At the time, our families were situated miles away from her college. When she failed, her family decided to bring her home. In the process of packing her belongings, my aunt spotted a heap of clothes relegated to a corner. "Is that your dirty laundry?" she asked, "Pack it up, we'll wash it when we get home". What my cousin said next was unbelievable. 

She casually replied, "You can wash those?" As it turns out, she had been discarding her clothes instead of laundering them. She claimed ignorance even though she regularly washed her underwear and bras. Now, she's back living with her family and started taking on more household duties to showcase her growing sense of responsibility. 

Yet she occasionally slips up, attempting to throw out her clothes with the same old excuse: she didn't know they could be washed and worn again. This makes me ponder about her thought process before college, when she was still at home and wore the same outfits more than once. She had to know that clothes can be washed, right?

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7. Royconomics

Once upon a time, I had a colleague named Roy. He had unique perspectives on how to navigate life. We affectionately referred to it as "Royconomics". One day, he decided to share his wisdom with me and another coworker. "Want to learn how to own fancy stuff?" he asked casually. 

His belief was simple, head to the stores, buy everything you covet on credit—fresh furniture, latest appliances, big televisions, trendy stereos, and then intentionally ignore the loan repayments as well as court summons. His logic was that even if the courts garnish your wages due to non-payment, the cost would still be less than what you would have paid ordinarily.

A week later, he had another epiphany to share. "Can I teach you guys a trick about how to buy a house?" he asked. His method was to apply for all the credit cards possible, withdraw the maximum cash limits from each, and then use this cash heap as the down payment for your dream house. 

Similar to the previous advice, he directed us to deliberately abstain from making any payments and also dodge any court summons.

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8. Lucky Bird

This anecdote is about a major blunder I made. At 16, my first job was with PetSmart. One particular evening, my duty was to clean the enclosure for the birds and small mammals. The cleanup process involved carrying a ShopVac into the small area and utilizing it to vacuum up spilled bird food, seeds, and litter. Sounds pretty straightforward, right?

So there I was, cleaning the cage housing the cockatiels. Suddenly, one curious bird decided to study the noisy vacuum cleaner more closely. Out of nowhere, FWOOMP! The bird was sucked into the vacuum tube. In a panic, I hurriedly used a box cutter to slice the hose in two to free him. I was in total shock. 

The bird was missing feathers and was bleeding. Barely holding back tears, I rushed to my supervisor exclaiming, "IACCIDENTALLYSUCKEDUPACOCKATIELINTOTHESHOPVACHESGOINGTODIEMAI'MSOHORRIBLE". One glance at me and the bird and my supervisor starts guffawing.

In the end, I took the bird to a different PetSmart that had an onsite vet as part of the store. The vet, who also found it amusing, hydrated the bird. My colleagues then affectionately dubbed the little survivor Hoover. He was kept in the back of the store in isolation for a few months until he regrew his feathers. 

Once he was back to his normal self, we put him back up for sale.

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9. What Are The Odds?

A few years ago, when the Mega Million Lotto skyrocketed to its highest-ever total, over a billion dollars, lottery tickets were flying off the shelves. At the time, I was employed at a 7/11 in Maryland. One day, a middle-aged woman strode in holding a bag chock-full of hundred-dollar bills. 

With a self-assured air, she plonked her bag on the counter and told my colleague, "I want 8,665 lotto tickets, please". Back then, the price of a single Mega Million ticket was $2 and 6 cents. I hastily punched some numbers into my phone calculator, and realized she had just dropped an eye-popping $17,849 on lottery tickets. 

This move left us scrambling as it also meant we actually ran short of ticket printer paper. As a result, other customers were left high and dry, unable to purchase any tickets for the next three days. As it turned out, her gamble didn't quite pay off; she didn't end up winning the lottery. 

I've never been particularly well-off myself, but from my perspective, losing $17,000, unless you're swimming in money, is a pretty significant hit.

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10. Big Regret

My pal surrendered her volleyball scholarship, which would've allowed her a free education far from home. She made this difficult choice because her boyfriend would be left behind—he wasn't college-bound. But she was unaware of a devastating secret. 

He was unfaithful to her and, adding insult to injury, broke up with her less than a year after she declined the scholarship for him. Now, she's continually plagued by regrets as she watches several of her friends join professional volleyball teams worldwide.

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11. My Strange Obsession

I once knew a man who left his family behind just to fully immerse himself in the My Little Pony fandom community. I'm not kidding. This happened back in the early stages of 2012. He was in his early 30s and was utterly convinced that he could thrive as an artist in the fandom community. 

The problem was, his art wasn't all that great. However, that could have changed had he been open to constructive criticism and improvement. He went to the extent of quitting his radio job to devote all his time and energy in pursuing his fandom artistry ambitions. 

He made many attempts to sell his artwork at fan conventions, which unfortunately didn't go so well. When his wife, a British ex-pat from a wealthy background, was presented with an exciting publishing opportunity in the UK, his life could have changed for the better. 

Her parents were willing to support their move, and a high-paying job at his in-laws company was waiting for him. His life would have been free of financial worries. However, to everyone's surprise, he turned it all down because the UK didn't host any Pony conventions. You heard it right. 

So his wife moved back to the UK with their daughter. She tried hard to keep their relationship alive and even invited him to visit them in the UK, but he wasn't interested at all. His entire focus was on creating MLP art. In the end, their marriage unsurprisingly fell apart and his wife divorced him. 

Since then, he hasn't made any attempts to connect with his daughter or his former wife. Fast forward to today, the My Little Pony fandom doesn't draw as many enthusiasts anymore, but he is stubbornly clinging on to it. He becomes defensive when anyone points out the dwindling popularity of the fandom. 

His mind appears to be somewhat out of touch with reality. On a positive note, his ex-wife has found solace in remarriage and their daugther seems to be doing well without him. It's doubtful that his daugther even remembers him anymore.

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12. Sad Song

My sister was a piano prodigy. She rejected a full scholarship to attend Juilliard for a Mormon mission in Los Angeles. However, three months into the mission, tragedy struck. She was hit by a car, which resulted in both her legs getting broken. 

Afterwards, she ended up back home, grappling with depression and guilt over what she perceived as having "let God down". She married, had a child, and then things got worse. She discovered her husband wasn't a nice person and eventually left him. Now she is a single mother, with no noticeable skills or financial cushion. 

I believe this series of life choices is probably one of the most regrettable our family has seen.

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13. What Am I Supposed To Do?

I had a date with a woman I met on the internet. We didn't really click, and I figured that was the end of it. However, a week later, she rang me asking for help, stating that I seemed kind enough and she needed someone outside her family and friend circle. With some reluctance, I asked her to elaborate. 

To sum a long story up, her grandmother passed shortly after our date, leaving her in a whirlwind of family drama and emotional distress. In her vulnerable state, she made a decision to escape by taking a trip to Las Vegas. Unfortunately, she ended up blowing every last penny she had, approximately $50,000, in the city of sin. 

Not only that, she even sold her return plane ticket and lost that money too. The only possession she was left with was her phone. Somehow, she had caught rides from Vegas to Victorville, and that's when she decided to dial my number.

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14. Vote For Me

My sibling decided to take a bold step: He ventured into politics without a well-prepared plan in place. He didn't have the advantage of leadership skills, relevant work history, or community backing. To fund his political bid, he secured a loan of $10K from his own pocket. His attempt ended in a resounding defeat and he ended up in the cold last. 

The loan repayment and refilling of his depleted savings—a consequence of financing campaign materials such as banners and handouts—took a significant length of time. The situation was both tragic and comedic. In a twist of karma, or just poor fortune, the printers produced campaign materials that all bore his name incorrectly. 

Now, the remaining leaflets and signs serve as a stark, yet funny, reminder of his unsuccessful political adventure.

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15. Let It Ride

I saw a man, clearly under the influence, bet a hefty sum of $2,000 on a single roulette number while on a cruise ship. He lost it all, then doubled down and withdrew another $5,000. He gambled it all on that same unlucky number and lost again, standing there looking at the table in disbelief. 

Afterwards, I strolled over to the ship’s bar, ordered myself a refreshing drink and thoroughly enjoyed it.

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16. Investment Opportunity

About 15 years ago, my buddy was fortunate enough to retire with a full pension. However, instead of enjoying a peaceful retirement, he was persistent about kickstarting a new enterprise with an acquaintance of his. He always used to tell me that his partner was the visionary of the business, while he had the savings and a strong credit ranking to rely on.

Without much ado, my friend went ahead and secured a consequential loan from a bank. With this, he bought a variety of high-end equipment. Little did he understand the complexities of this venture. Unfortunately, barely half a year in, the business collapsed. To add salt to injury, his business "partner" mysteriously disappeared along with all the valuables. 

So here he is, my buddy, who should ideally be relishing his retirement days, stuck in a retail job to make ends meet until who knows when.

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17. No, Don’t Bother Listening To Me

My best buddy recently exited a longstanding marriage of 18 years, leaving his wife and two kids for my former girlfriend. I did my best to caution him about her history—she was unfaithful in her prior relationship, entangled with another man and me, and she enticed him, a married man, to be unfaithful to me. 

She spun a web of lies to keep everyone, including my buddy, in the dark. She's quite the puppet master, setting herself up as the innocent party while deflecting any blame for her actions onto others. I'm aware that she painted her version of reality to him, yet despite this, he insists that "she had a rough last year, and he won't hold past errors against her". 

Oddly enough, less than two months ago, she was describing my buddy to me as a controlling, bullying, narcissistic man. I have a vision of the chaos that is about to unfold. I can't help but envision the monumental problems he'll face when she eventually strays from him, all the while crafting stories to make herself seem like the wronged party. 

It's clear to me that this may be the most crucial error he's ever committed. I did my best to enlighten him. Still, one can only hope that their love will endure, and they'll achieve their fairy-tale happy ending.

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18. Big Fish, Small Pond

In my quaint hometown, I observed two fellows who believed they ruled the roost. Sadly, it led to their downfalls. As time passed, they came to the shocking realization that they weren't superior in every way, nor were they entitled to get whatever they craved just on the assumption they deserved it. 

Distressingly, one of them ended up succumbing to addiction, and the second man is but a mere shadow of his once robust high-school self, visibly beaten by life.

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19. Dumpster Fire

My friend was nearing 30 and felt it was time to leave her mom's place, largely because she believed it wasn't suitable for someone her age. She was a single mother of two young kids, having recently left an awful relationship with their father. 

Her job paid just a bit above minimum wage, but she found an apartment where the rent would consume 80% of her salary. I tried to tell her over the phone that it may not be the best decision, but she wasn't convinced.

After moving in, she struggled with finding reliable and convenient childcare, and often drove against traffic to drop the kids off at her mom's place. She was barely making it every month and even had bills piling up. Eventually, she allowed her ex-partner, who hadn't treated her well, to move in. 

Surprisingly, during this period, she began an affair with her married boss. I couldn't help but ask why she didn't just opt for someone from a dating app like Tinder. But she brushed it off, claiming that only weirdos and creeps use such platforms—which seemed like quite an irony, considering her current affair with a married man.

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20. Is That All There Is?

A man of middle age who I am acquainted with had been living what is often considered to be the dream life. He resided in a mansion valued at $15 million, was in possession of several boats, and was the owner of a flourishing business. Additionally, he had a beautiful wife and children. But, unexpectedly and abruptly, he let all of this slip through his fingers. 

I am not completely abreast with the specifics, but what I know is this—he embarked on an illicit affair with a minor and developed a dependence on painkillers. His soaring, dream-like existence took a sudden nosedive pretty quickly. 

At present, he continues to be amongst the living and is in the grueling process of reassembling his life, having lost his family, his opulent home, all his material wealth, and his flourishing enterprise.

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21. L is for Loser

Right now, I'm dealing with my ex-husband. At just age 25, it feels strange to call him that. He left to be with an 18-year old, which, honestly, was okay. Surprisingly, being a single parent has simplified things for me. On occasion, he shoots me a text expressing his longing for me and the kids. 

It's not like I'm barring him from seeing his children. But oh, the self-inflicted drama and pain he carries with him. Yet it's me who ends up in the firing line. All because I want him to purchase diapers for our kids and request child support, he accuses me of trying to ruin his life. 

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22. Get Out The Popcorn

Over the last few months, I've been observing an old friend and former roommate of mine allowing his life to spiral out of control. We're both in the prime of our twenties. Recently, he got a woman struggling with addiction and bipolar disorder pregnant. 

They weren't in a committed relationship, just an attempt to move on after a breakup. But since she chose to keep the baby, he seems to be just going with the flow rather than seriously contemplating the lifelong implications of parenthood with her.

He has a history of finding himself tangled up with emotionally unstable women, but he rarely stands up for himself until it's far too late. Unfortunately, this time, it seems the realization may not come until after the baby is born. 

So, for now, all I can do is sit back, watch events unfold, and prepare myself for the storm of drama that is likely to impact our group of friends in the coming months and years.

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23. Life Comes At You Pretty Fast

During our junior years in college, a friend of mine sported a perfect GPA. She stood out amongst us with her smarts, beauty, and humor. She had vet schools lined up and even enjoyed a full scholarship—she was blazing the path as the first ever college graduate in her family. 

Then, she found herself expecting a child from a man she only knew for a couple of months. Disturbingly, he was a domineering and terrible person. On the bright side though, he had a well-paying job as an oil driller. However, that ray of hope was short-lived when he was fired just three months before their baby was due. 

My friend, by then heavily pregnant, welcomed him into her life. She literally took care of him, and eventually, she quit college to marry him, winding up back in her tiny hometown. She occasionally sends me messages, savvy attempts to rope me into some pyramid scheme or the other. 

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24. Don’t Tell Dad

When I was a kid, my mom somehow found herself in a financial pickle. Not wanting my dad to know anything about it, she began to hide all the mail and made it a point to never pick up the phone. The situation kept spiraling out of control, so much so that she started to hide dad's mail as well. 

Each time before she'd step out, she'd remind us kids to toss any letters that turned up in the mail. We never fully understood why, but we just knew that mom would throw a major tantrum if she discovered we didn't obey her orders. However, dad started to grow suspicious as he was continually unable to locate his mail.

For some time, I kept saying I had no idea about the missing mail just to avoid stirring the pot. But, all things explosive have a trigger, and this was no different. One day, dad stumbled upon a pile of unopened bills. This revelation led to a massive fight. Turns out, mom owed quite a hefty sum. 

Dad was understandably upset, but they decided to stick together. However, if I were to tell the truth, the dynamics of their relationship have changed since that day.

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25. This Floorplan Is Nicer Anyway

Once upon a time, my folks were having a house built. Unfortunately, the workman who marked out their foundation made a big blunder—he used the wrong plans. He marked out entirely the wrong house. This error cost him his job, but before the company let him go, they tried to pull a fast one on my dad.

In an attempt to rectify the situation, they tried to convince my dad to switch to a different house model, one that the mistake wouldn't affect. But my dad stood his ground and responded with a firm "no". Then, they tried to shift the house to a different plot of land. Again, dad said "no" to that proposition. 

Next, they tried to make him bear the cost of tearing down the wrongly constructed foundation and preparing the ground for a new one. Of course, he strongly opposed that as well. All this led to a massive clash between my parents and the home building firm. Lawyers got involved, and the stress of the situation nearly caused my dad to have a heart attack. 

Finally, they ended up with their dream house, but the process was drawn out far longer than expected due to the company's mistake and subsequent pushback.

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26. Suspicious Much?

I was in a relationship with a woman for half a decade and she hailed from a troubled home. This had left a deep impact on her, leading to severe trust issues, particularly with men, believing that they're all dishonest. I tried everything to earn her trust, from sharing my passwords to sending her my exact location in real-time. 

Unsatisfied, I asked her if tying the knot might help her feel more secure. She replied with a simple "yes". Thus, I decided to pop the question, but my proposal didn't meet her high expectations and I was advised to “try again," with a grander scheme in mind.

I diligently saved up for another half a year and secured a booking for the venue. As I started inviting her friends, a shocking revelation unfolded. "Look, I like you, so I need to tell you something," said one of them during a call, “She's been involved with another man for the past three months and they’ve been spending every evening together after work". 

As of now, she's single and spends her days bemoaning about how men can’t treat her right.

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27. Imaginary Wife

I saw a buddy of mine walk away from his bride-to-be right before their wedding day. Oddly, he'd formed this idea in his mind about what a "typical" wife ought to be and he felt she didn't fit that mold. Today, he's filled with remorse. His ex-fiancée tied the knot with a mutual friend and they're living a fairy tale life. 

Meanwhile, he has yet to find someone new.

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28. Trapped Inside

The most glaring mistake I've seen is observing friends and family continue to be part of an evidently controlling cult, where every facet of their life, from their meals, their daily routine, various daily choices, their earnings, even their clothing is regulated. 

As someone who managed to break free from this cult, it's staggering that anyone could remain, especially given the abundance of historical documents and even the cult's own records that essentially debunk their religious claims. The falseness of it all is so profound, it's beyond any form of debate.

I am eagerly waiting for the day when my loved ones truly embrace their own lives and discover authentic joy. The cult is now toning down some of its stringent regulations in a bid to dissuade members from walking away, but there's a limit to how much they can relax these rules without contradicting their fundamental beliefs. 

Even after my departure years ago, I still find myself grappling with the task of unlearning the thought patterns and lifestyle it enforced.

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29. Never Do Business With Family

Back in 2005, my mom decided to re-mortgage her house. She did this to invest in a house-flipping business. This new business venture was recommended by her cousin, who assured her it was a great opportunity. Unfortunately, it turned out it was all smoke and mirrors, a scam. 

And if that wasn't enough, the housing market crashed in 2007. As a consequence, she almost lost her home and she's still tackling the resulting debt to this day. Prior to this, mom was already battling substance use. But these unfortunate events took a great toll on her and sent her down a tougher path. 

Consequently, she ended up losing her driver's license and her job. It was a difficult time for my siblings and me. Her cousin wasn't just irresponsible with other people's money. He even managed to convince his own parents to invest in this fraudulent business. Sadly, they ended up losing the bulk of their retirement savings. 

Understandably, this has left a bad taste in everyone's mouth, and now most of the family avoids any interaction with him.

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30. Is That Any Way To Say Thanks?

I was there when my cousin tied the knot with a fellow who was seeking a US green card. Their entire courtship had lasted a mere four months. Despite everyone's warning that the guy's behavior screamed trouble, she was firm in her conviction that their connection was genuine love. Not too long after, they welcomed a baby. 

With the added responsibility, he believed she had no escape and began physically hurting her. Alarmingly, even though she left him for a period, she returned, stating that he had transformed. However, the cycle of abuse resumed. Essentially, she repeated her mistake. They've since separated. 

The harsh reality is, if a person is agressive once, the tendency to repeat it remains.

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31. Lowered Expectations

The experience of my brother with an online scam was truly heart-rendering; he's disabled. He found a woman on the internet whom he got genuinely attached to. Although she resided on another continent, he was convinced she was his soul mate. They spent over a year sharing texts and emails. He even assisted her financially, which came across as suspicious to me. 

Despite my doubts, he wouldn't listen. Eventually, he managed to put aside enough money to pay her a visit. Clearly, it went badly. He came back after only two days, and despite the clear signs, wouldn’t admit what had transpired. Sadly, he carried this burden silently till he passed.

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32. Keep It Shut

A family member of ours, along with their spouse, chose to have an open marriage with other people. Sometimes, this could work out, but sadly, in their situation, it went terribly wrong, leading to infidelity, ill-treatment, and eventually, a split. Now, five years on, they're yet to finalize their strenuous divorce. 

Honestly, it's the most contentious divorce I've ever witnessed. This ordeal has wreaked havoc on the lives of four people so far.

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33. What Were You Thinking?

We're close friends with a particular family, a pair of lovebirds who have celebrated over 30 sunny anniversaries together and have three lovely girls, all in their mid to late twenties. It's a bustling, energetic household, frequently buzzing with lively social events. 

The father held a prestigious position as the managing director at a well-known brewery and dining spot in town. Surprisingly, he made the poor choice of engaging in an extramarital affair with an employee, who, to put it kindly, lacks rational thought.

This regrettable act had catastrophic results, leading to a bitter end of his marital bliss and shattering his family. Adding insult to injury, he also lost his esteemed job at the restaurant. Now, he's entangled in a volatile relationship with this unstable lady, who has a tendency towards physical aggression towards him. 

This entire saga unfurled over the past year. It's been an utterly bizarre and sorrowful spectacle to behold, and one we've tried to maintain our distance from.

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34. Trainwreck

I've just seen my cousin, for the fifth time now, pack up and move out aimlessly. No plan in mind, no place to go, and she's in the company of disingenuous individuals—primarily because they're after her disability benefits. She even had the audacity to swear at our grandma when she attempted to lend a helping hand. 

As a consequence, she was evicted from a community center, a place that's notoriously difficult to gain admittance into. Her current place of rest is one of the most treacherous parks in town. Tonight, I'm planning to have a heart-to-heart with her, but honestly, I'm at a loss. This situation has been unchanging for months.

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35. Paperback Writer

A lady from my workplace decided to resign to follow her passion for writing; she loved creating narratives. But there were a couple of obstacles. She'd never actually written anything before and she hadn't done any research into how to earn a living as a writer. 

I tried to propose the idea of keeping a part-time job, at least initially, to guarantee some form of income until she could fully support herself through writing. She was a mother of two and as far as I was aware, her husband's earnings weren't substantial. 

Her response to financial concerns was that it wasn't going to be a problem because she planned to "write bestsellers specifically”. It was the most significant facepalm moment I've experienced.

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36. Success Story

My best pal struck up a relationship with a lady who was seeking refuge. They found themselves on the brink of calling it quits until she cajoled him into a few additional nights of intimacy. This led to her pregnancy, and consequently, he tied the knot with her. 

He took the initiative to renovate his childhood home for their new family, but she dismissed it as unattractive and insisted on an upscale condo instead. This lady had no aspirations for employment, so my buddy became her financial backbone. 

Next, she organized the relocation of her entire family from their homeland—her parents, along with seven siblings. This meant my friend bore the brunt of their upkeep. To add to his burdens, they expanded their own family with four more kids. My friend harbored suspicions that at least one of the tots might not be his.

Fast forward a decade and my friend's life has taken a dramatic downturn. He's had a full-fledged mental breakdown and now lives on the streets without a dime to his name, completely estranged from his children. Meanwhile, his ex-spouse has managed to carve out a quite comfortable life for herself. 

She's locally renowned, partially thanks to her involvement with a charity championing rights for immigrant women. Her charm and good looks have furthered her popularity as she regularly graces news and local TV as the organization's ambassador.

Ex-Employers’ Hidden SecretsPexels

37. Ignorance Is Bliss

This is a tale from my own life. At the age of 18, I found myself employed at a local bagel shop. I was still getting to grips with the job when a patron walked in and placed his order. It sounded to me like he asked for a bagel with "a whole lot of cream cheese". 

Following his instruction to the letter, I incinerated a bagel under the toaster and then heaped a generous portion of cream cheese on top. He handed over his payment and exited the shop. But not for long. Minutes later, he was back voicing his dissatisfaction loudly, insisting, "I ordered LOTS of cream cheese!"

His request struck me as absurd. How much cream cheese could a single individual possibly desire? So, with bewilderment and a dash of rebellious spirit, I piled on two gargantuan scoops of cream cheese worthy of an ice cream sundae onto his bagel. I wrapped it up carefully and sent him on his merry way. 

But lo and behold, he was back in a flash, now seething with anger and shouting, "I ordered LOTS of cream cheese! What's not to get?" I defended my actions, explaining that I had indeed provided him with copious amounts of cream cheese. 

I couldn't even begin to comprehend how anyone could stomach MORE cream cheese than the quantity I had already given him. We're talking two ENORMOUS scoops here. Then, as if the clouds of miscommunication suddenly parted, an amused expression emerged on his face. 

Then he revealed, "I ordered LOX and cream cheese! LOX, you know, smoked salmon!" At that point, it hit me like a ton of cream cheese. Ahooogah!

Worst MistakeShutterstock

38. Get Here ASAP

Once upon a time, I found myself working alongside this guy at a McDonald's right here in Ohio. We had a typical workplace friendship. Then one day he came in, announcing it was his last day and that he was quitting. Naturally, we were all curious about what led to his sudden decision. 

He then shared that he had met a girl online only a few days before, who had managed to convince him to leave everything behind and move in with her in Providence, RI. We all attempted to make him see reason, outlining why his plan might not be the ideal move, but he wasn't interested in hearing any of it.

We even questioned him on his plans to reach Providence, to which he outlined a rather reckless strategy. He was going to rent a car using a credit card. Once he got the car, he planned to cancel the card to dodge the rental charges. His idea was basically to commandeer a car without paying for it. 

Of course, we attempted to make him understand this approach was not smart. He brushed aside these concerns as well. After that day, we never saw or heard from him again.

Worst MistakePexels

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39. Life Choices

When I first crossed paths with my boss, he was something of a prodigy in our division. Despite his young age, he had noticeably climbed through the ranks much quicker than most. Even though he happened to be younger than me, he had already taken on a managerial position. 

I'll admit, I didn't aspire to tread his path, but his rapid progression in life was always obvious to me. He was the type to consistently monitor his credit score while at work, yet he proportionately made some questionable decisions, like simultaneously leasing a pricey motorcycle and car.

Our professional journey ultimately diverged when our office closed down, forcing us to head off to different locations. Transitioning into this new chapter, he swapped his two high-end vehicles for a much simpler car, built a connection with a woman who had six children, all from different fathers, and was considering marrying her—only a month into knowing her. 

Now, don't get me wrong, I have immense respect for single mothers, having been brought up by one myself. But, this woman was by no means a hardworking individual. Fast forward a bit, he ties the knot with her, they quickly have a child together, and she becomes a stay-at-home mom as he takes on the role of the breadwinner.

Unfortunately, life took a darker turn when she introduced him to illicit substances and betrayed him multiple times. Things reached a critical point when he attempted to end his own life by consuming an overdose of pills, driving recklessly into oncoming traffic, and ending up crashing his car in a hospital parking lot.

Miraculously, the hospital staff were able to revive him. What's the shocker? After surviving such a close call, he chose to return to her. In my opinion, that's the most detrimental error I've observed anyone making.

Woke Up In A HospitalWikimedia Commons

40. What A Fool

Once upon a time, there was a not-so-clever guy at my high school. He was generally harmless until midway through high school when he made the puzzling decision to turn himself into a thug. One particular day, he decided to walk into a class full of freshmen who were without their teacher. 

Being bold enough, he blithely snatched electronic gadgets, cash, and other essentials at blade-point, not even bothering to hide his face. Before slipping out, he audaciously dropped his real name, Jim Conrad. He warned them, "Make sure you don't mention it was me, Jim Conrad, who nabbed all of your belongings".

Conrad then left the school premises. But instead of hiding his good outside the campus, he, for some unreadable reason, returned with all the items stashed inside his backpack. To protect his cover, he lurked around his victims' class with his loot-laden backpack intending to eavesdrop on the students while the authorities were gathering statements. 

His goal was to ensure the students weren't snitching on him. However, ironically, they all pointed fingers at him. Upon hearing his name in connection with the theft, Jim lost his cool and disrupted the ongoing statement collection session by charging back into the classroom. He threatened to harm the students if they didn't retract their accusations. 

Meanwhile, the authorities who were still in the room watched him in disbelief as he still had all the goods on him. Needless to say, he was apprehended on the spot and subsequently expelled from the school. The entire incident was so baffling that all we could do was collectively facepalm.

Teachers Got Fired FactsShutterstock

41. On Fire

This takes me back to a time when I shared my living space with a roommate. One time, I was startled by a sudden cry of alarm from the kitchen. I instantly ran in and found him wildly waving a flaming paper towel, which he was gripping in such a way that the fire was dangerously advancing towards his hand. 

Acting swiftly, I told him to let it go and stomp it out immediately. The story that unfolded still astounds me. Apparently, he decided to turn on our gas stove while a paper towel was suspiciously close. It's beyond me how someone could yell out in terror about a fire about to harm them yet do absolutely nothing to prevent it. 

I understand that was his response in a panic, but what if I wasn't there?

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42. One Small Thing

I knew this guy whose career was in the field of windows and doors. He spent years fine-tuning his skills on high-quality homes, liaising with architects during the early stages, and collaborating with clients and contractors towards the end. For a man in his late twenties, it was a pretty cushy setup. 

The pay was satisfactory and his enterprise was flourishing. Some of the tasks were complex, requiring top-notch project management. Hence, he had to be present on-site a few times every week. The particular assignment I'm referring to had all custom work, including paint, wood, mill work, glass, and hardware. 

The entire job came with a hefty price tag of over $750,000 and he functioned as a freelance contractor responsible for supplying the materials. For a period of nine months, every single detail was meticulously structured. It took a solid two days just to review the specs individually. 

Both the client and contractor gave their approval on each aspect. Once he received the initial payment for the materials, he went ahead and kick-started the order. Move forward six months, and all materials were ready. The contractor was set to go. Delivering to the wet, messy site was a task and a half. 

It took three journeys spread across five days to simply transport the windows. So far, everything was sailing smoothly. The contractor gave it his go-ahead and all he had to do was sit back and wait for the final payment. And then, the phone rings.

It was the interior decorator on the line saying, "The windows are the wrong color". As a result, he had to foot the bill for the incorrect windows, the cost of sending out a team to replace them, and basically everything else. Eventually, he found his business in ruins and enrolled back in college just to get by.

Plot TwistsShutterstock

43. Grand Theft Auto

Buddy, who once worked for a car rental business, had responsibilities such as car cleaning, preparation, and pre-rental inspections. On a regular workday while parking a cleaned truck, he was approached by a couple of older, scruffy-looking men, which was a typical occurrence.

"Hey, we've just finished up inside, and the girl in there told us that truck's ours," one of them declared. Gut instinct, playing on autopilot, Buddy handed the keys over, saying, "Alright, enjoy your ride!" Strolling back to the office, he bumped into his boss. 

She queried if he had interacted with the two men from the parking lot, to which he affirmed, "Sure, they're the ones who rented the truck". Suddenly, his boss stood frozen, mouth agape, and exclaimed, "NO!" Panic-stricken, she quickly dialed emergency services.

Weeks turned into an agonizing wait and the rental firm was informed that their trashed truck was found abandoned in a remote area. Buddy was then assigned the unenviable task of identifying the culprits from a picture lineup at the station.

Ruined Jerk's Day FactsShutterstock

44. The World, Ontime

Right after college, my buddy and I landed jobs in the post room of a significantly sizeable company. We often handled parcels labelled "Overnight" or "Next Day AM," which seemed to be of earth-shattering importance if not delivered on time. 

It was my friend's duty to make sure these were dropped off at the appropriate boxes before the collection time. This meant he needed to transport these away from work and deposit them. However, on one particular Friday, he had a crucial piece of mail that he unintentionally neglected. 

The letter remained overlooked in his vehicle the whole weekend. Upon returning to work the following Monday, he discovered the CFO and several higher-ups in a state of sheer panic because the said mail had not been received. As it turned out, the piece of mail was a check worth half a million dollars. 

The recipient company had been eagerly waiting for it, threatening some kind of legal steps otherwise.

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45. A Fine Performance

During my time at Chuck E Cheese, I witnessed a pretty chaotic scene that involved one of my coworkers, a pizza, and two little kids. Picture a bustling restaurant, children darting to and fro, wreaking all sorts of playful havoc. 

Amidst all this, my coworker had the task of delivering a pizza to a customer seated at the farthest corner of the place, which meant he had to skillfully swerve through a labyrinth of games and kids. He was almost there, just 10 feet away from the customer's table when the unexpected happened. 

Right before him, a tiny toddler, barely two, was crawling on the floor. He tripped over the little one, sending the pizza airborne, which, unfortunately, made its landing on another child. Instantly, there were wails from both children—the one he accidentally stepped on and the other who got a pizza shower.

But the mayhem didn't end there, he then had to face the furious parents. Just thinking about it still gets me shaken. With tempers flaring, they demanded my coworker be fired. But our manager was understanding. He refused to fire him, but in a bid to appease the irate parents, he pretended to scold my coworker vehemently. 

It was an Oscar-worthy performance from a non-actor, which managed to calm the parents down satisfactorily.

Ex-Employers’ Hidden SecretsPexels

46. As Loyal As A Golden Retriever

My father made a decision to leave an $80,000-per-year position in a show of unity with his team after the company disbanded their department and handed out pink slips. He could have kept his job at that same pay level but chose to stand by his colleagues, which compelled him to resign too. 

As a result, my parents ended up depleting their savings, losing their home, and landing in bankruptcy. One might say they did it out of principle?

Worst MistakePexels

47. Hollywood Or Bust

My buddy dreamed of stardom in Hollywood. Leaving his job and letting go of all his belongings, he spontaneously set off for Los Angeles. Since we are from Canada, he had to cross the border. Here, he was faced with the routine inquiries from the border officials. 

His aim of seeking work and residency in LA without a valid work visa didn't sit well with them. Unfortunately, this resulted in him being denied entry into America and he had to resort to moving back in with his folks.

Overheard messedPexels

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48. Wowwww

I can hardly believe what I had to witness. A relative was duped into becoming the adoptive parent to three kids, all because a so-called "friend" claimed to have Stage 4 cancer and was on her deathbed. Shockingly enough, after the whole adoption process was completed, the "friend" mysteriously began to recover and decided to abandon her family. 

She moved overseas, leaving my relative behind as a single stepparent. Now, she has three kids who, quite unfortunately, do not hold her in high regard.

Questionable Paternity factsShutterstock

49. All For Nothing

My colleague maintained a relationship with her boyfriend, who served a 20-year sentence for taking someone's life. He was released, and together, they leased a house, took loans for a car and a motorcycle, and adopted a pair of pit bulls. She singlehandedly footed the bill for all of these expenses. 

During those same 20 years, she also assumed responsibility for raising his son from a prior relationship. However, just two months following his release, he impregnates another woman and abruptly leaves my colleague. Despite our repeated warnings, she now finds herself saddled with debt and reflecting on the 20 years she invested in him.

Crazy ExesShutterstock

50. No Thanks, I’m Done

Let me tell you a story about a man who suddenly decided that he no longer wished to be a husband or a dad to his two children. No interest in custody, no desire for responsibility. As far as anyone could tell, there wasn't another woman in the picture. 

He didn't move to another town, nor did he switch jobs. But he seemed to have lost the will to bear any responsibility. He was about to face some unexpected consequences though. He quickly realized that there was a widespread stigma attached to walking away from your kids voluntarily. 

His coworkers, who knew about his situation, stopped engaging with him. Even his own family disowned him, not before giving him a piece of their mind about his irresponsible behavior. Those who might have considered themselves his friends distanced themselves from him. 

His ex-wife, quite justifiably, took him to court and nailed him for full child support and alimony among other things.

Lawyers Screwed factsShutterstock

Sources:  Reddit, ,


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