These Dates Ended In Disaster

October 18, 2023 | Eul Basa

These Dates Ended In Disaster


It takes a lot of mental preparation and courage to go on a date in this day and age. You just never know who you'll end up meeting—it could be your soulmate, or it could be your worst nightmare. The following stories are of the latter case, and they may just convince you to stay single for a while...


1. She Booked It

Upon our arrival, he asked for a kiss within the first few minutes. I consented, and wow...there were immediate sparks and loads of butterflies. Our conversation was going smoothly—but his demeanor changed quickly.

Touching my backside, brushing past my chest while his arm was draped around me—moving me closer to him by pulling my hips...all these gestures felt quite premature for a first date scenario. He seemed overly interested in kissing and didn't pay heed to my attempts to change the course of the interaction. 

By this time, roughly 15 minutes in, things started feeling a bit off. I suggested numerous times, "Let’s just continue getting to know each other", to which he responded with a startling comment: "I want to learn more about you but in the restroom".

His bewildering comment was open to numerous interpretations, all of which were far from pleasant. A pickup line including the term 'restroom' was absolutely stomach-churning. Eventually, I excused myself citing work commitments, but he audaciously tried to convince me to quit my job and spend the day with him, inviting me over to his place. 

His assumption of not needing to work after our imaginary wedding was the last straw.

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2. He Was Off His Noodle

He preferred his pasta cooked just right—slightly firmer than usual, or al dente, yet with a slight softness. He was intensely fussy about it, assuring me I had the knack for getting it to his taste better than he could. Once, after a long day that ended a gruelling 12-hour shift, and an almost one-hour commute, I returned home to him.

His first words to me were, "I'm starving. Whip up the pasta." Given his past tantrums and my fatigue, I chose to silently agree and prepare his beloved pasta. Whether it was sheer tiredness or another factor, I miscalculated the cooking time, and the pasta came out softer than usual.

I served it, sprinkled the seasoning, laid the plate on the table for him, and headed off to shower and sleep. Unaware of the looming threat, I was in the middle of undressing when pasta came flying at the wall next to me.

Then, something hit the back of my head, and the next moment, I found myself on the bathroom floor with the color of red dyeing the tiles and everything else blurring. He had my neck in a vice-like grip, hissing, "You'll pay if you ever serve me overcooked pasta again."

When I came around, he was back to watching TV as if nothing happened. I tried to slip away to seek medical help, but he spotted me. Blocking my exit, he wore a terrifying grin that still gives me shivers, "You're not leaving before I get my rightful pasta."

I managed to break free later that night and run for help. I ended up with a concussion and a cracked rib. The necessary authorities were informed and I managed to secure a restraining order. Colleagues came to my rescue to retrieve whatever left of my belongings from the apartment, as he had tossed most of them out or ruined them. 

That incident confirmed—this man was a dangerous menace, and he meant his threats.

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3. Licky Licky

I bumped into this guy at a café once. He seemed friendly and we had coffee again, finally deciding to get dinner at a pub. As we sat at the bar, something really unexpected happened. I was just trying to catch the bartender’s attention when he decided to lick my face, sliding tongue from chin to forehead. You could easily tell I was taken aback.

Attempting to dial down my shocked expression, he playfully poked me. I asked him to stop and his response was rather creepy. He leaned in and whispered, "I'll just poke you while you're asleep”. I couldn't stick around any longer. I made sure he left, and even had a bouncer escort me to the door to make sure I was safe.

Days later, he began to message me. He seemed worried because he hadn't heard from me and was planning to "swing by my parents' house to check if I was alright". I never told him anything about my parents' home or where they lived. Fed up, I warned him I'd contact the police if he ever bothered me again.

Luckily, I never heard from him after that incident.

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4. Nothing To Think About

My first date was a peculiar one with a guy who worked on cell phone towers. He arrived in an old, tattered, and sweaty T-shirt. Almost instantly, he assumed the role of an amateur psychologist, claiming I was afraid of men, even though I had courageously met him at a state park. 

He confessed he'd grown weary of treating his dates to fancy steak meals and sweet ice cream, with no relationship progression. He boldly proclaimed that moving forward, he'd reverse the dating process, choosing a trip to the bedroom over a costly dinner. 

He insinuated that I had some serious thinking to do and assured me he'd patiently wait. But honestly, I didn't need any extra time for contemplation. He made a shocking revelation: he told me that his wife had passed away merely six weeks before our date—only six weeks! How could his perspective on dating have soured so quickly?

He proposed a follow-up call, to which I, reluctantly, agreed while mentally deciding: "He can try phoning, but I won't pick up".

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5.  Social Media Psycho

For a couple of months, I was seeing this guy. He was relentless in his efforts to get me to declare my love for him and battled with my firm stance against having kids. He'd weep and hope for a middle ground, but for me, that wasn't a negotiable thing.

I found a good reason to end the relationship given I wasn't as committed to it as he was. His erratic behavior didn’t manifest until after I broke up with him. He'd persist with messages about "fighting for me," whatever that meant. He even claimed he had practically turned into a father figure for my cat in the short span of three months.

He alternated between pleading for me to return and threats. When I blocked his texts, he'd move to Skype, so I blocked him there, then on Facebook, Instagram, and so forth. His messages grew increasingly more malicious over time.

He resorted to calling me names and spreading rumors about a supposed other person in my life. To be safe, I changed all the codes and passwords around my house in case he'd somehow learnt about them. He soon began to bother people we were mutually acquainted with.

He began harassing my best friend, claiming he'd put a restraining order on me and warning that I should await a notice in the mail. He threatened to sue another girl I knew for defamation and picked fights with various people in our social circle. Eventually, everyone blocked him as well.

Turns out his behavior wasn’t so extraordinary as other girls started talking about their similar experiences with him. Things did finally calm down after a few months, until recently when he tried to follow me on Instagram. I blocked him immediately, and he surprisingly found my outdated Flickr account.

He sent me a message there, apologizing for his past behavior and advising me not to delete my Instagram account. But I steered clear of responding; I just hit delete.

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6. Signs From Above

We decided to go out for a stroll, and let our playful side out as we rolled down a green hill, which was conveniently located behind a Mormon Church. However, our fun was interrupted by a passerby, who happened to be a Mormon. He told us that what we were doing was not appropriate for that location, and in a rather unsettling manner, watched us as we got dressed.

Seeking privacy, we moved to a different location. Unfortunately, we weren't able to enjoy ourselves fully, which left us both feeling rather unsatisfied. To add to our troubles, our fresh spot was home to a horde of mosquitoes. I ended up with about thirty bites on my behind and a couple more in rather uncomfortable places. Meanwhile, she had the misfortune of rolling over onto some dog droppings, which really upset her as it was only on her.

Almost as if the universe was sending us a message, it echoed, "You should get a room."

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7. He Didn’t Exactly Bowl Her Over

A few years back, I was setting up a first date with a guy, and he proposed the idea of bowling. I let him know that bowling was fine, even though my last attempt at it was ages ago and it was a total disaster. He kindly offered to teach me, I suggested we save the lessons for next time. 

What I really wanted was a laid-back, casual setting where we could get to know each other. So, he agreed to go bowling without the teaching, making a joke out of my non-existent bowling abilities. I felt good about it.

However, when I got to the bowling alley, things took a nosedive. He began to instruct me right off the bat. He gave unsolicited advice about my stance, correcting each of my bowling mistakes. He criticised that I wasn't taking the game seriously and added on saying, "I’m trying to teach you for your own good". 

Although he was adamant about teaching me, he didn’t seem to be enjoying himself. The only time he smiled was when he saw me initially. I reminded him that I had hoped this date would be fun and relaxed, not a training session. However, he responded that I'd have fun if I were serious about the game. 

Surprisingly, he seemed genuinely upset about the whole situation.

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8. Plenty O’ Fish In The Sea

I visited his place before he returned from work, a typical move for me since I knew his computer password. I found that he'd left two dating sites—Plenty O' Fish and Cougar Life—open and was signed in. 

My instinctive reaction was, "Seriously, man?" When I checked the messages, it became clear that he'd been arranging to meet other women local to us for some time. I phoned him and he became anxious.

He tried to convince me he'd set up the account for a friend. I immediately saw through the lie, but I wanted some kind of resolution. I decided to wait for him to return from work—a decision I later regretted. When I broke up with him, he reacted badly: he grabbed my phone and keys, locked me inside, physically kept me from leaving, and did his best to keep me there.

This was incredibly terrifying. He was physically larger than me and I'd never felt so powerless. He shouted at me loudly, his throat veins were bulging, and he held onto my arms as tight as he could. I ended up hiding on the couch, in a sort of mentally detached state. That's when I realized how aggressive he truly was.

Finally, I managed to calm him down and he let me leave. I was so stunned by the incident that I didn't report him to the police, even though I had bruises on my arms and felt shaky for several days thereafter. 

It was much later that I discovered he'd previously been charged and had held another woman against her will. I regret not going to the authorities at the time because I'm convinced he would be in jail after his second proven offence.

Shockingly, I REUNITED WITH THIS GUY, and we stayed together a few more months until things got even worse. After our ultimate breakup, he made attempts to connect with me for YEARS. I still sometimes panic when I hear a man shouting at a woman, and unknown phone numbers still make me nervous.

Occasionally, I look his name up in the court records, hoping to find that he's either in jail or no longer alive.

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9. Money Matters

He took me out to an Italian diner. While our order was being prepared, his phone rang. He had a bit of small talk with the caller, who, it turns out, was his mom. Mid-conversation, he said, “Mom, relax, I chose the least expensive item on the menu. And yes, I'm here with my girlfriend. I'll give you the bill details later.” There were a couple of issues here.

First, this was our FIRST date, and I was definitely NOT his girlfriend yet. Second, although him living with his mom wasn't a big issue for me, the fact that she was heavily involved in his financial decisions to the point of calling him during dinner to check on his expenses was a bit off-putting and downright bizarre.

I decided to see him one more time to make sure he was as odd as I thought, and then I decided to call it quits.

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10. It’s Been A Slice

My first date with this guy took place at a pizza joint. When he insisted on ordering for both of us, I knew it wouldn't end well. To my dismay, he served me a minuscule slice of wood-fired pizza that left me wanting for more. And before I could even reach for a second helping, he boxed up the remaining pizza and stashed it away in his car trunk.

Quietly, I stepped away to ring up a friend to collect me, as revealing my home address to this man was out of the question. Two years have passed, and I'm still peeved about missing out on that flavorful pizza.

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11. News Flash—I’m Gone!

On the day of 9/11, my former partner and I were informed about the planes crashing into the towers. We were driving to a cafe where I was planning to work on my thesis. 

After the second report, I mentioned, "That wasn't accidental". He was quick to belittle my assessment, persistently ridiculing me for suggesting that the crash wasn't accidental, insisting it had to be a mishap since no one would willingly instigate such an event.

Once we reached the cafe, they had stationed a television in the restaurant's center for customers to follow the unfolding news. We sat there, watching. The moment a tower collapsed on the live footage, tears sprung to my eyes. I was painfully aware I had just watched countless innocent lives being taken away.

I couldn't help but wonder, “My God, how many were still trapped in there”? Adding to my worry, my brother was airborne at the time—although, fortunately, he was unharmed—and a friend was employed in New York City's financial district. I was distraught, like anyone with a shred of compassion would have been.

He slung his arm around me, seemingly to soothe me, yet his next words were ice cold. He whispered, "You're creating a scene and embarrassing me. Either stop crying or go wait in the car". That was the turning point; I knew our relationship was over.

We cohabitated, which prompted me to time my departure tactfully. A few weeks later, I planned a night out with my pals which he opposed, becoming irate whenever I savored a bit of enjoyment. During the heated argument, he cornered and threatened me, saying, "I wish I could punch you right now", followed by cruel laughter.

The following day, I packed my stuff while he was away at work. I was certain then; his emotional side seemed irreparable.

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12. Running Him Ragged

I accidentally turned a promising first date into a bit of a disaster. I completely miscalculated the time it would take for him (and I say this as a woman) to cover a distance of seven miles on foot. In the end, I had to enlist a friend's help in phoning the park ranger's hotline to inform them we'd still be out on the trail after 9 pm, well past the gate closure time.

By the time we covered two-thirds of our walk, he began to concern me—he was giving morale-boosting talks to his own legs and contemplating eating the frogs that were jumping around on the path. 

I had to use my mobile to light our path because it was incredibly dark and he had forgotten his. I owe you an apology, mate. You were an absolute gem. I had no intention of hiking you to near exhaustion.

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13. She Over Shared

During our initial meeting, the lady flips open her laptop and presents me with a film of her undergoing "natural childbirth" in a pool, accompanied by her previous partner. 

The camera angle reveals all the details, including the crowning head of her child making its debut. Suddenly, her current seven-years-old child shows up and excitedly exclaims, "Oh, this is my favorite clip!"

That's when I realize, I'm not the first guy she's shown this video to. Unsurprisingly, there won't be a repeat rendezvous.

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14. Festival Of Lies

For months, my buddy's girlfriend had been frequently visiting a particular city, claiming her mom was diagnosed with lupus and needed her assistance. One day, she ended things with my friend, saying she was unable to give him the time he deserved because of her current situation.

He took the news well and wished her all the best. She even hinted that they might get back together when her mom's health improved. That weekend, she kept updating him via text about the struggle in caring for her mom and about sleepless nights spent at the hospital.

As the supportive friend he is, he kept texting her back with lupus research and words of encouragement. However, something strange happened a few days later. While casually scrolling through Facebook, he stumbled upon a 360-degree photo from a music festival located near his ex's mom's city. It was posted by a guy she used to see before him.

He noticed his ex in the photo, clearly enjoying the festival. Far from being at the hospital, she was partying at this music festival and apparently rekindled her romance with the guy. He discovered more photos of her from the festival, revealing that she was there for the entire weekend, contrary to her claims.

At this point, he questioned everything, including if her mom was really sick or if she was just spending this time with the other guy. Upon confronting her with these facts, she vanished from his life without a word. She could've ended things without resorting to lies, but she chose to maintain a deceitful charade while enjoying her single life.

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15. Drink Up

So, I connected with this girl on the internet and we kicked off quite smoothly with frequent text exchanges. One day we decided to meet over dinner. All seemed to go pretty well, although she did appear slightly unusual.

We decided to have margaritas. Halfway through our chat, she ceased talking and just blankly stared at her hands. When I inquired about her wellness, she confessed to being inebriated. I was surprised as we'd only had one drink, but she laughed it off saying she'd been drinking all day.

Reflecting back on the texts where she'd confessed to being drunk, I sensed a pattern. Suddenly she face-downs onto the table in what I mistook for a hyperbolic jest. After I helped her sit upright, I asked for the bill, which turned out to be quite heftier than anticipated.

She asked for help to reach her home, forcing me to agree because she seemed pretty unsteady. The supposedly short walk turned into a mile-long trek. We finally reached her place, she offered water, and suggested I stick around. But having had a strange evening, I chose to leave only to witness an angry outburst. I giggled my way out, navigating via GPS back to my car.

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16. A Real Mess In Aisle Three

While at the supermarket, I bumped into a man I didn't know and he invited me to dinner. The date was less than stellar, largely due to the fact he spent most of the time criticizing my vegetarian lifestyle. At the end of the evening, as we were heading back to our cars and saying our goodbyes, he felt inclined to ask for a kiss. I declined. Yet he persisted and asked once more. I rejected his request again.

Then, he proposed, "How about a small kiss on the cheek?" Just to get him to leave me alone, I agreed to the harmless gesture. And that's when he did it—unexpectedly, he turned his face just as I leaned in, landing a kiss right on my lips. This was the one thing I told him I didn't approve of. After that episode, a second date was out of the question. 

I avoided all of his phone calls and texts. His last message read, "Why is it that this always happens to me?"

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17. He Was A Different Brand Of Crazy

One night, my boyfriend decided to host a get-together around his backyard fire. It was a chance for me to meet his friends. We found common ground with a couple of his buddies, bonding over similar movie preferences. Let me be clear, there wasn't any flirting involved. 

When everyone was heading home, him and I were by the backyard gate. Suddenly, he hooks my belt loop and tugs me his way. With all honesty, I thought he was going after a friendly hug— but he had other thoughts. Apparently, he wasn't too thrilled about my camaraderie with his mates, and thought they might "snatch me away" from him. 

Somehow, he made it seem like it was my fault. It was bewildering. His hand was gripping a stick he had earlier picked from the fire. His intention wasn't to draw me into an embrace.

His actual plan was to "mark" me with the glowing end of the stick somewhere hidden. The scar remains, but he doesn't.

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18. Drama King

This is essentially a story of a breakup that went down on a date. I attempted to end things quietly with him in our car together. His response was to halt the conversation, guide us into a restaurant, only to start crying publicly.

The most interesting part is, several weeks afterwards, he waltzed into my workplace acting as if we hadn't split up. So, I had to go through the process of ending things again with him...while he sobbed...and all this happened in front of his sister, who also happens to be my colleague...

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19. He Came To Save The Day

Looking back, one date really takes the cake for being hilariously terrible. You know, I met this fellow on the internet and we hit it off pretty well. Then we decided to finally meet face-to-face. He had seemed quite normal, but oh boy, was I in for a surprise when we actually met. 

He showed up in full superhero gear, mask, cape, the works! Completely flabbergasted, I didn't even know how to respond. Although I attempted to roll with the punches and make the best of a bizarre situation, it was just too much. I never saw my caped admirer again and I seriously doubt I ever will.

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20. Nothing Was Real

For nine months, I was in a relationship with a real piece of work. He was dishonest about his job, his history, and even lied about his parents not being his biological ones. Trivial matters would set him off, causing a public spectacle.

If I was just a few minutes late picking him up, he'd blow up. He once created an unbelievably awkward situation during a pleasant family dinner because he thought I was chatting too much with his sister. It got so loud that it even annoyed the neighbors.

Once he moved in with me, I started noticing some of my money and jewelry had gone missing. I later found out the shady truth—he was pawning these items, and the receipts were hidden behind some furniture. He even falsely claimed he had cancer to prevent me from taking a much-needed business trip.

Meanwhile, I was the only one bringing money into the house. Despite my commitment and sacrifices, he had the nerve to fake a serious illness. It turned out that the healthcare center he was claiming to visit didn't offer treatments for any of the conditions he had supposedly been diagnosed with. After he moved out, I discovered a suspiciously sickly toned makeup he used to feign illness.

I tolerated this whole farce much longer than I should have, finally reaching my breaking point after seven months. My ensuing therapy journey to unpack everything left me wary and distrustful when it came to future relationships.

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21. Telling Tall Tales

Once, a friend asked me to be their escape from an awkward date. Suddenly, she excused herself to use the restroom, and I had a hunch that's when the call would come. After returning, she continued our conversation for a little while. It turned out, her excuse was quite surprising.

Rather than resorting to the old "my friend needs me" routine, she told me an intense tale: a bus accident with several fatality victims, urgently drawing her back to the hospital. That was quite unexpected, to say the least.

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22. She Never Asked

Back when I was in my late 30s, I went on two dates with a woman. Throughout both outings, she didn't ask me a single question about myself. Despite her being incredibly chatty and fond of sending funny memes and perfectly fitting emojis in our text exchanges, she didn’t show any interest in getting to know me during our face-to-face dates. I realized too late that this was a warning sign I should've paid attention to.

Her favorite topic was clearly herself. She never once asked, "How are you?", "How's your day?'', or even, "How's work?" When I ultimately decided not to pursue a romantic relationship and suggested we stay friends, she lashed out, calling me every negative name under the sun, like a "loser" and a "jerk." She even spitefully told me, "I could do so much better than you."

I was taken aback by her outburst, realizing she had some unresolved personal issues. I calmly told her that maybe she should find someone better, someone who could handle situations like the one we found ourselves in. I also pointed out she wasn't really losing anything. In fact, she was gaining a chance to meet someone else who'd be a better fit.

She responded by falsely accusing me of being selfish and only ever considering my own interests. "You never think about me! It's always about what you want to do!" she said.

I had to remind her, "We've only known each other for two weeks! Your reaction makes it seem like we've been dating for a couple of years!" I genuinely felt sympathy for her, as she seemed to be harboring some emotional wounds from a past relationship that had yet to heal.

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23. Scrambling To Survive

My ex-partner had the nerve to report me to the police for things he was actually guilty of. It was a confusing and uncomfortable circumstance for both the detective and me to untangle. The man broke my car's ignition system causing it to ignite into flames while I was driving on the highway.

Despite me fainting and being a frail, sick 90-pound woman, he had the audacity to claim that I, not he, a massive 300-pound aspiring linebacker, was the attacker. He even went as far as stalking me on college grounds, having his friends inundate my phone with calls, practically making my existence unbearable until I managed to transfer schools. 

Nonetheless, he still had the gall to insist that all these actions were my doing.

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24. Good Enough

My first date was a disaster. We had an incredibly tiresome car journey with him going on and on about his fascination with nightclubs and pricey bottle services. Finally, we reached what he charmingly referred to as a "just right shabby spot for a girl like you". 

After he placed our orders, he felt the need to verify his bank balance before he made rude suggestion. It caught me off-guard—he said that I should pick up the dinner tab...not that I have a problem with paying, just wish he had asked nicely.

It didn't stop there, with him monopolizing the conversation through dinner. He enthusiastically delved into his outlandish beliefs, like the earth being flat and his aspiration to be a senator on Mars in a decade. He indicated that any woman seriously involved with him must be supportive. Post-dinner, since he was driving, I was unwillingly ushered to a club.

When he declared, "Things are going great!" I felt compelled to clarify that they were not, considering I hadn't been given an opportunity to speak yet. He asked me to provide examples, so I pointed out that this was the worst date I'd ever had. His response was chilling. Sitting down next to me and throwing out the idea of us being "friends who might become more".

I instantly booked an Uber to escape. Despite my clear disinterest, he kept texting me for another date every day for a full week, leading me to finally block his number.

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25. She Was A Little Crazy

I once had plans to meet a lady I'd connected with online. Naturally, you always question if their in-person appearance will match their profile picture. 

Well, imagine my shock when a woman, who's eight months pregnant, walks in—a detail completely left out from all her photos and our chats. I decided to continue with our meet up, as I didn't have the heart to abandon a single, expectant mom.

Turns out, she was grappling with severe depression and hadn't been taking her medication. What's more, she confessed her overwhelming and ever-lasting love for me within the first hour. Here's a quirky bit about her: she and her father, who I had the chance to meet, were rather petite. 

They lived on a farmland in a cozy little house that was custom-made to accommodate their heights. Being quite tall, I couldn't help but feel like Gandalf paying Bilbo a visit.

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26. Two-Faced Terror

I once dated a guy for a long time who exhibited some peculiar habits. Once he became absorbed in an activity, he'd forget I was there, even if he'd invited me over. If I had plans without him, he'd somehow make me feel bad enough to cancel them and opt to spend time with him instead. 

He was possessive to the point where I was almost always in his company, and he'd even keep tabs on what I was up to. He'd even snoop on my phone. I remember one instance where a friend of mine pecked me on the cheek in his presence. He laughed it off initially, but later lost his cool with me. 

He was like a chameleon, showing different sides of himself to different people. Gradually, he morphed from a caring boyfriend to my solitary custodian. Thankfully, one day, he abruptly lost interest in me, as if a switch had been flipped.

Having the relationship ushered to an abrupt end was painful initially, but looking back, I'm grateful. He was later medically identified as someone living with schizophrenia.

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27. Shortchanged By The Universe

I got to the cafe much earlier than required, thanks to my jittery nerves. No sooner had I parked did I realize that my wallet was still at home. Here I was, half an hour away from my house with just 10 minutes to spare before our meet-up.

Quickly rummaging through my car, I managed to scrape up $2 worth of loose coins. I sprinted into the shop and bought the least costly coffee I could find. She walked in shortly after, looking puzzled as to why I hadn't waited for her. I suppose it seemed less than chivalrous not to offer to pay for her order with the remaining coins jingling around in my car.

We found a spot outside, where I positioned myself facing the setting sun. Through all its blinding rays, my stubborn pride wouldn't let me shift. So there I sat, squinting through our entire one-hour conversation. The chat itself was actually quite enjoyable! But then, right at the end, as I shifted in my seat, I heard a loud CRACK.

That's right, my wooden chair had split. Sure, I'm not exactly small, but why did this have to occur right then? So, when she didn't call me back after our disastrous date, I was hardly taken aback.

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28. Three Strikes He’s Out

On my first date with this guy, I mentioned that I work in statistics. He jumped right in, belittling my profession and calling it useless and insignificant. It's a bit disheartening, seeing as that's my career we're discussing. Later, when I told him the ages of my cats, 10 and 11, he responded with a disturbing statement: "From a statistical perspective, they're almost at the end of their lives."

During one part of the date, possibly when we were strolling to the car, he nonchalantly expelled a spray of mucus from his nose. He didn't even bother to ask for a tissue. He simply did it, turned back around, and carried on as if it were a normal occurrence. So, when I communicated that I didn't feel a spark between us, he seemed genuinely taken aback.

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29. Baby, You Crazy

He asked me to grab a gift he's bought for his buddy's baby shower. I headed to the shop, requested the item, but they told me no order existed. I rang him and handed my phone to the shop assistant. A bit later, she gives it back to me expressing, "I won't tolerate being spoken to in such a manner". I felt completely lost.

The shop assistant felt he mistreated her verbally and declined to assist me further, so I walked out. Once home, he claimed innocence and got upset with me for siding with her. 

Later, he accused me of ruining everything, declared that we weren't attending the baby shower, and his friend was really disappointed. Feeling helpless and miserable, I reached out to his friend to apologize.

But his friend hasn't got a clue about what I'm mentioning. Turns out, he concocted the whole scenario to portray me negatively. That moment opened my eyes. He has been manipulating me, making me question my sanity throughout our three-year relationship.

My Date Turned Out To Be PsychoUnsplash, Obie Fernandez

30. Well, That One Backfired

I haven't been on too many dates, but the most memorable—and hilariously awful—one happened thanks to Tinder. Initially, the idea was to kick things off with a group date at my place, then if all went well, we'd venture out as individual couples afterwards.

But, the last part of the plan fell through. Why? Well, he used my bathroom, ended up clogging the toilet with too much paper, and felt mortified when my buddy walked in right after. He dashed out that fast, he even left his coat behind. And the best part? He was so embarrassed, he sent one of his friends back to my place the following day to fetch it.

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31. This Little Fiesta Went Siesta

We had our date in the middle of a hot, humid summer day. We grabbed some tea, and he was keen to sit outdoors under the bright sun. He kept discussing engineering topics, unable to spot my fading interest. 

Out of the blue, I found myself drifting to sleep. I can't tell how long I was out, but woke feeling warm, perspiration-soaked, and utterly unamused. What's bizarre is that he continued his monologue even while I was napping.

These First Date Red Flags Will Have You Swiping LeftFreepik, DCStudio

32. Rewind The Tape, He Did What?

I was blissfully wedded for nearly 24 years. He was consistently charming and brought positivity into every day. That was until he got arrested for indecent exposure in an AMC cinema's parking lot during a busy matinee hour, and horrifyingly, when children were around. But the most shocking part? He was using his workplace's postal address for the official documentation.

Upon further investigation, I found alarming facts hidden from me. Not just once, but multiple times he was taken into custody during our marriage without ever disclosing it. Additionally, he was held by immigration services twice, as they questioned about his son's whereabouts—except, we didn't have any children. 

Faced with these revelations, I moved for a divorce as soon as the office opened the very next day. After that, he disappeared from my life completely, without a trace.

My Date Turned Out To Be PsychoPexels

33. Dr. Yuck

So I inquire about his work and he modestly replies, "I try not to gloat, but I save lives on the daily." His profession? A doctor, and frankly, he wasn't joking about it. However, he was visibly upset because he had asked me out via a dating app five years prior but I hadn't answered right away.

When I explain that it was due to an inactive account he retorts, "This just proves that girls are so unpredictable..." Want to hear the cherry on top? He finally confesses that he has strep throat and shouldn't really be out on a date. Disgusting!

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34. He Wanted The Full Package

I once connected with a man on a dating app and we arranged to meet at a public park. He was an ex-military man without a job and he seemed to be dealing with some mental health issues; although, this was not immediately apparent during our text exchanges. 

Upon sitting down for a chat, he quickly told me about his terrible living circumstances and asked if he could move in with my kids and me. He even offered to look after them while I was at work.

I expressed that it wasn't a suitable arrangement and that's when his attitude drastically changed. He became infuriated. I attempted to clarify that I barely knew him since we had just met, and I found it disappointing that he thought it was acceptable to ask such a thing, especially considering how protective I am of my children. 

Throughout the conversation, he was unnervingly insistent and became irate when I didn't agree with the plans he had already conceived for us.

Towards the end of our meetup, he realized things weren't swaying in his favor and demanded to know if I had any intentions of dating him. When I firmly responded with a "no", he once again grew angry and stormed off. 

Soon after, I received a message from him reproaching me for the expensive gas he used to travel and meet me; he assumed that I should have fulfilled his expectations. Remarkably, he felt that I owed him something since I couldn't provide him with a place to stay and financial assistance.

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35. Gut Instinct

Once upon a time, I met a girl whom I thought we had really connected with. We had similar interests, but there was something niggling at me, making me think something wasn't right. So, I decided to step back from the relationship but aimed to stay on good terms with her. 

I later discovered she had been playing a game all along, only pretending to share my hobbies in a bid to win me over. As the story unravels, after I ended things, she became so upset that she smashed a glass against her door. And when her roommate came to clean up, she melodramatically uttered, "No, leave it. 

Those are the fragments of my broken heart." So, as it turns out, not having any regrets and trusting my intuition was the best call.

My Date Turned Out To Be PsychoPexels

36. Third Time’s The Charm

During my second year in high school, I planned to catch a film with the girl I was dating. But at our first stop, the movie theater required an ID check for the very first time. Being under 18, I couldn't grab the tickets. Things just kept getting worse from that point on.

We then tried a second venue, only to have the film screening canceled due to a faulty air conditioning system, which caused the temperature to spike to 95 degrees.

Our third option didn't have any neighboring seats for us. She was still eager to watch the movie, so we ended up sitting in SEPARATE ROWS. As you might guess, we didn't have a second date after that.

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37. She Walked Away With It

This lady and I were on a fantastic initial outing, and we got a bit carried away with the drinks, even belting out a few karaoke tunes. In my bubbly and joyous state, she slyly convinced me to show her a family heirloom ring I carried. 

My heightened spirits blinding me to my mistake, I didn't realize she'd kept the ring when she departed hastily, using a vague excuse, something about having to fetch something.

Shockingly, it appears she wasn't truthful at all, not even about living in my hometown. Since then, she's vanished without a trace, sadly, taking my precious ring with her.

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38.  Prove Your Love

I'm not sure if his behavior is characterized as psychopathic or sociopathic, but during the last part of our two-year relationship, my boyfriend made a terrifying threat. He claimed he was going to jump out the window from our apartment on the 11th floor. 

The window was wide open, and all that was keeping him from plummeting was a waist-high barrier. It seemed like an endless block of time while I held him back, preventing him from making this dreadful leap.

We were both in pieces, yelling and crying. Eventually, I managed to drag him back from the perilous balcony. As we tumbled away from the window, I knocked into the TV and he landed on top of me. The most shocking part was when he got up, casually dusted himself off, and revealed his threat was empty.

 He claimed he was only testing my love for him through this twisted act. That's when I recognized the level of his manipulation and finally had the strength to end things.

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39. A String Of Bad Luck

To be honest, it's tough for me to pinpoint the worst date I've been on, as there have been quite a few shockers. I once went out with a woman who seemed perfectly normal until she opened up about her conviction that we're all part of the matrix.

I also had a relationship with someone who had a biting habit. This led to going to work and visiting family with visible bites and bruises on my neck, from her nipping and tugging. It felt like I was in real danger. In another instance, a date left me alone at a club when I found myself out of my introverted safe space.

I had to walk home after that, and to add insult to injury, I ended up wetting my pants. There wasn't much concern on my part at the time as I was battling a depressive episode and was too drunk to care. So, as is clear from these examples, my journey into the dating world has been anything but smooth

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40. The Spy Who Loved Her

On our initial meetup, he claimed to be studying medicine at our local university. This raised suspicions since I was aware there wasn't a medical school there. I wondered if maybe he was doing his pre-med studies, and so I agreed to a second outing. During this meet, he spent significant time explaining how he worked for the military in Iraq as a contractor doing 'espionage' work after serving in the army. He broodingly added, "If only you knew the stuff I've been involved in!"

During that same date, we swung by his place to grab something. While at his apartment, I saw a sight that made me hugely anxious—all of his mail was addressed to a different name than he'd given me. Thankfully, I conveniently received a 'work emergency' text. I used this as an excuse, saying that I hurriedly had to tend to some work issues.

After letting him know that there wouldn't be a third date, he became eerily enraged. I wished never to see him again, but unfortunately, that did not happen: I spotted him lurking in the bushes around my apartment several times. Finally, I had to take out a restraining order against the name he provided me with. I didn't see him after that event—and what a relief!

These First Date Red Flags Will Have You Swiping LeftFreepik, wirestock

41. Slow, Subtle Sicko

At first, he'd simply compare me to his former girlfriends, but always in my favor. He was extremely eager to join the hobbies I enjoyed alone. He'd push his way in, whine or mock subtly throughout and it became progressively worse. Although his jokes seemed harmless and I'd laugh them off, they started to escalate.

Then the underhanded compliments started—insults disguised as compliments. When I'd react to these, he'd claim he was 'Just kidding,' with a smile that never reached his eyes. One night while we were hanging out on the couch, he out of the blue said he didn't want to live anymore. I took him seriously and started to ask more.

He quickly denied having said it, shaking his head in a dazed manner. It spiraled downwards from there, culminating when he choked me in a fury. He apologized, called me, and even sent me flowers. My sister was there for me thankfully. I hadn't shared much with my family about what was happening because he was progressively alienating me and I felt delusional.

I began questioning if I was reading too much into his comments and hints. The moment he choked me, I ran to my sister without a second thought. I abandoned everything back in his house and moved on. It took a number of years and meeting better people to finally heal from it.

My Date Turned Out To Be PsychoPexels

42. Is That My Ride?

One time, a friend's buddy asked me out. He snagged my digits, phoned me up, and invited me out to dinner. He also asked if I'd mind his work car picking me up. Having had some experience in the corporate sector, I thought it's just a company car—no biggie. In retrospect, I probably should have asked about his profession.

As the awaited evening rolled around, he showed up... in a trash truck. Sounds crazy, right? But there's more. Deciding to go with the flow, I said, "Why not?" and headed out for our meal. I believe he must have had some serious butterflies in his stomach because he ended up getting a little too tipsy—so much so that he dared to ask if I could drive his enormous truck home.

Imagine this: a massive vehicle with not one but four gear shifts. I only know how to drive automatic, just to clarify. Therefore, Mr. Tipsy had to drive me back, in his waste management truck, before asking if he could stay the night.

Let's just say there was no "next" date...

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43. It Wasn’t A Good Fit

So, she suggested that we have our first date at a shopping mall—which struck me as quite odd. When we finally met at the designated place, she surprisingly brought along her young child. I, too, am a parent, so I wasn't too bothered, although a prior notice would have been appreciated. She went on to tell me that her plan was to pick out an outfit for her child, as they were doing a family click for a Christmas card later that week.

The situation felt a bit awkward, but, navigating through the shopping aisles? I thought, why not give it a try. But then, things took an unexpected turn. She began comparing clothes against me, and when questioned, she responded that I almost resembled the build of her ex, who was also joining the portrait session. She even went ahead to ask me to try on some clothes so that she could visualize how they would look on her ex. Rather than heading to the changing room with the selected clothing, I chose to locate my car instead.

Thankfully, we had chosen to come in our own vehicles, allowing me to make an exit without leaving her in a lurch.

These First Date Red Flags Will Have You Swiping LeftFreepik, peoplecreations

44. Sweet Jesus, She Was Crazy

I once dated a girl who was quite difficult. She once lectured me for a full two hours after we narrowly missed a bus and a delay of just ten minutes. While I was immersed in a challenging college course, I restricted my phone usage, particularly around exam times. If I didn't reply to her messages swiftly, it didn't sit well with her.

She insisted on meeting up almost every day of the workweek and expected two-hour phone conversations every night. On one occasion, while we were at my parents' place, she demanded sweets. My family didn't usually keep sweets at home, and obtaining some would have required a 15-minute trip to the nearest shop. She accused me of infidelity on four separate occasions, likely corresponding to the days I didn't call her.

The situation deteriorated further after our breakup. She took it to the extreme by threatening suicide and having my friends text me pleading for reconciliation. She crafted fake online profiles to reach out to me, which I subsequently blocked. Resorting to getting new SIM cards, she bombarded me with calls and text messages, including annoying prank texts at ungodly hours. All of these numbers were subsequently blocked.

As a parting shot, she slept with one of my friends in an effort to provoke me and made unsuccessful advances towards another friend of mine.

My Date Turned Out To Be PsychoUnsplash, Ryan Snaadt

45. Playing With Fire

My initial date was undoubtedly my most disastrous one. The girl began striking matches, extinguished them with her fingers, and then chose to consume the scorched portion of the matchstick.

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46. He Had A Killer Sense Of Humor

A couple of years back, I met this dude on Tinder for a date. His demeanor was unnerving as he often joked about how unsafe it was to meet with strangers from internet dating sites, and what if he was going to hurt me. These creepy jokes, combined with his overall unpleasant attitude, started to make me feel uncomfortable.

Now, to escape this unsettling scenario, I asked a friend to call me pretending to have an emergency. The strategy worked, and soon, he dropped me at my friend's place. But what happened next was just downright scary. Instead of driving off, he got out of the car and entered the house uninvited. What's worse, he only begrudgingly agreed to leave when asked, but then weirdly stood there scanning us.

When we urged him again to leave, he agreed but asked for a strange favor from me—escort him to his car. With the fear that he might exhibit odd behavior again, I reluctantly obliged. So, outside, we reached his car, and then he just paused and gazed at me.

I said goodbye, and hastily back-tracked towards the house when, out of nowhere, he demanded a goodbye hug. Terrified, I instantly spun around, bolted into the house, and secured the door. But, this didn't seem to deter him. He sat in his car outside, persisting via text that he wouldn't depart until I rendered him a hug and a kiss.

After being met with complete silence from my end, he eventually quit and left. So yeah, you could argue that his behavior was a pretty big red flag.

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47.  Stuck Between A Rock And A Hard Place

I was in a relationship for two years with a girl during college. It took me an awfully long time to realize she was a bit unhinged. Some signs were nuanced when we were together, although she tended to be quite bossy. After breaking up with her, that's when the real madness started.

As part of my summer job with the college, a group of friends and I were given free accommodation on campus. She had a similar setup, but in a different department. By this time, we had parted ways. Strange thing was, she would be found crying on a large rock outside my hostel whenever I passed by.

If I was with friends, her piercing stares would follow us. There would be times I'd pass by with a female friend, and within two minutes, I'd get a message asking if I was dating her instead. The hostel was shaped like the letter 'C' with a courtyard in the center.

While my room was on one side of the building, a friend's room was directly across the courtyard. One evening while at my room, I got a call from this friend who'd spotted my ex, cloaked in black, hidden in the bushes beneath my window, trying to snoop on me.

Confronting her immediately, she claimed to be at Walmart. Fast forward six months post our breakup, there I was at a spring concert in college, enjoying one of my favorite bands with my new girlfriend, who is now my wife.

Lo and behold, my ex was there too. She brushed past us, evaluated my present partner, made eye contact with me and said, "This is fine. I don't care. This is totally fine," before simply walking away. Looking back, I can't believe I was with her for TWO whole YEARS.

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48. Just Watch Me

The most terrible date I've experienced happened when I was in boarding school, right on campus. We were a pair of straight-laced nerds and decided to hit up a party at our student center. After we'd been there for about a quarter of an hour, my date became rather disinterested in the whole affair, and we slipped away from the party crowd and into the compound.

Here's where I thought things might get interesting—possibly a little bit of good, old-fashioned lip-locking? No such luck.

Here's what he did next: he discovered a computer lab and, for the next two hours, had me sit there and watch him play a video game called League of Legends, all the while making unsuccessful attempts at explaining the game's nuances to me. Here's a nugget of wisdom I gleaned from the experience—if a handsome guy is single, there's probably a good reason for it!

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49. It Was Bad From Five Minutes In

After nine years of marriage, I ended up single again. I wasn't particularly in the mood to hop back in the dating scene, but my friends encouraged me to. My first date back on the market was nothing short of a catastrophe. 

We chose a local restaurant as our meeting point and within the first five minutes, she confessed to eating a sandwich in her car beforehand on the off-chance I couldn't afford both our meals and drinks.

Fast forward to the seven minute mark, she suggested that I consider a career in food service. According to her, these establishments seldom check one's background—even in the face of false accusations from her former employer at Little Caesars. 

At the quarter hour mark, she reassured me I needn't be concerned about her around my children because she would never be drunk in their presence. Yet, she felt the need to clarify that she might be somewhat tipsy, but never seriously intoxicated.

Twenty minutes in, she expressed her appreciation for me because I appeared clean. In juxtaposition, with her last partner, she had injured her ankle slipping on some discarded pizza in his bedroom during a spontaneous romantic encounter. 

The old pizza on the floor proved to be no deterrent for their activities. Despite the intense and desperate advice from my friends to give it another go, we did not arrange a second date.

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50. Bad Romance

There was this one time when my ex and I were in the car, and the song "Bad Romance" by Lady Gaga started playing on the radio. I decided to turn up the volume a little and sang to the tune. 

His reaction? Total meltdown. He erupted into a fit of tears and yells, convinced that I was hinting about our love life through the song. I attempted to reassure him it was merely a song I enjoyed!

However, he stuck to his belief that our relationship represented the "Bad Romance" in the song and saw it as a forecast of an upcoming split. Even 15 minutes later when we reached his home, he was still completely upset. It ended up being his parents who had to step in and bring some clarity to the situation.

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51. It Was Like Watching A Car Crash

In her online profile, her photo was pretty appealing. We chatted about ordinary stuff four or five times before we made plans to catch a movie. I'm not a huge fan of movie dates as they restrict chatting and getting to know each other, but I figured, "She's pretty, what could possibly go wrong?"

Let me make it clear, she picked the movie showtime and also decided when I should pick her up, so it's not like she wasn't aware of her bathroom needs. Her place was roughly a 15-minute drive to the theater. The moment she hopped into my car, she appeared a bit tipsy and warned me with a kick-fight if I pulled any pranks. All this unfolded in barely 10 minutes.

At the 10-minute mark, she demanded, "pull over," so I did. Her next move left me dumbfounded. She stepped out of my car on quite a busy highway and relieved herself in plain sight...it was one of those situations where it was tough to look away. Once I snapped out of my shock, I reached over, shut the passenger door, and hit the road.

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52. She Only Got A Hug

So, I had a date with this lady and, for the most part, she was glued to her phone. There was even a moment when I paused mid-conversation to see if she'd pay attention. Nope, she didn't. As she wasn't carrying any cash, I landed up footing the bill for all the drinks. 

Sadly, the situation got grimmer. She wondered out loud if I was open to buying ketamine with her. And sure enough, she had the audacity to call her dealer right in my presence.

Seeing this, I grabbed my jacket, readying to depart, when she began shedding tears. We had a short talk, during which I hugged her and asked if she needed anything. 

Her response made me sigh, hard. "Perhaps a tenner?" I wasted no time making my exit. Afterward, she shot a text my way, suggesting we meet again. But let's be clear: there was zero chance I'd be spending another minute with this woman.

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53. Time To Get Out

It was just a normal Sunday night. My ex-husband had been unemployed for some time, and he knew full well that I had dozens of employee time cards to approve before the start of work on Monday—a process that took me up to an hour and a half every week for the past three years. He was also a heavy drinker with a short fuse.

On this particular night, he took issue with me sorting through the time cards after spending an hour preparing dinner for him and our son. Because I couldn't afford a sofa, I was sat on the living room floor, attempting to balance my dinner and my work. His voice, demanding that I put my work aside and give him my full attention, filled the room.

Before I had a chance to tell him that I was almost finished, he approached me, plate of food in hand. He took a substantial bite of tilapia, chewed it thoroughly, and without warning, spat it out all over my face and keyboard. It completely shocked me.

The idea that the man I had married would spit food in my face and over my work was unthinkable. I just sat there, stunned, but knew that it was time to remove him from my life.

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54. The Double Date Disaster

Right, so the story begins with my very first date. Yeah, first date in my 16 years of existence. I didn't know what to expect and the guy was kind of cute at school, so you see, my expectations weren't sky-high. Nevertheless, he still managed to perform below par.

I have a wariness towards people, so I insisted we date with another couple joining us. Considering he had a wide circle of friends that I was familiar with, he assured me this wouldn't be an issue. However, on arriving at his home, I found out that his dating partner was none other than... his aunt, who he lived with.

Two young ones, aged 21 and 16, on a date. Super, right? Her date then showed up, unaware he was part of a double date. Unbeknownst to him, he was accompanying his friend, babysitting her young nephew and his new sweetheart. He happened to be Polynesian, and she decided to cook Hawaiian haystacks.

He was clueless about Hawaiian haystacks but was greeted by the smell of extremely overcooked rice, courtesy of our incapable cook. He managed to rescue the rice, the remaining meal was magically concocted from a can, and it was surprisingly pleasant. They had nothing planned, and spontaneously decided to join us in throwing blades in the backyard.

I outperformed my date, which annoyed him, and then his aunt accidentally shot him in the butt with an airsoft BB, much to his chagrin. Hoping to rescue the situation, his aunt proposed bowling next. I was wearing ballet flats, which meant I had to wear his oversized, nerdy, decade-old socks—an outfit choice sounding multiple alarms I didn't want to investigate further.

Off we went to bowl, but not before he attempted to assert his macho side by stomping on a spider on the wall. His leg went right through the wall and got stuck. His aunt had to unstuck him. Not very impressive if you ask me.

Eventually, we arrived at the bowling alley and were met with a horribly awkward situation—the manager was his aunt's recent ex. Finally, the date comes to an end, he decides to go in for a kiss in the back seat of his aunt’s car as his aunt and her date looked on. His aunt reacted by cheering.

I wish I could say that was my last date with him, but it wasn't. It wasn't even the worst high school date I had endured.

The Worst Dates EverPexels

55. She Had It Down To An Art

I once had a date with a girl who works at a very famous neighbourhood art museum. She described art using the most mundane, lifeless, and unclear language I could ever think of, rendering it hard for me to keep up. When I asked her questions, she belittled my knowledge. 

I did my best trying to chat about art—which I actually adore, by the way—but ended up feeling less smart. Safe to say, there was no follow-up date.

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56. She Ain’t Got No Alibi

One day, the police rang me up and inquired whether I had been spending time with this woman I was seeing at the time. It surprised me because they knew details about every meal and movie we'd shared, down to the receipts she had kept. It seemed that she was trying to establish me as her romantic excuse.

Following that, they asked me to take a look at the day's newspaper headlines. What I saw left me shocked—she was being accused of pushing a four-year-old child out of a flat window. 

The strange part was her claim that dating me was proof she wouldn't have done it, because she had moved on from the child's father. At that moment, the chilling realization hit me: she was unhinged.

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57. Taste Test

He dipped his fingers into my dessert, tasted it, and then repeated the act! I had ordered a lemon meringue pie and kindly suggested that he try a bit. First he declined, but then said, "Actually, that looks tempting". Next thing I knew, he had his fingers right in there. Just gross!

The Worst Dates EverShutterstock

58. She Waited Six Minutes

I had an interesting encounter while out on a date with a lady. Only six minutes in, she asked about my income. Confused, I questioned the relevance—she told me that she had zero plans to sustain herself post-marriage. 

In her mind, she wanted to secure a partner whose earnings exceeded a certain benchmark. I can't recall the exact figure she quoted, but it was considerably high and far from my current earning bracket.

Seeing the dissonance, I gently pointed out, "It seems we might not be a good match, then". She reacted with disappointment, labeling me another 'penniless underachiever' with unrealistic expectations of dating, despite my inability to shoulder her prospective financial dependency. Needless to say, I excused myself shortly after.

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59.  Time To Hit The Road

One day, while my girlfriend and her mom were deep in conversation, they started discussing strategies on how best to keep a boyfriend 'in line'. They saw this as a teachable opportunity. What astounded me was that I happened to be in the room and they acted as if I wasn't even there. 

My girlfriend even brought up a past action of mine she wasn't fond of. Her mother directed me to come over and brace myself for physical punishment that in my opinion could possibly injure me.

Looking at it, I'm a towering 6'3" guy with a stout frame. There was no way I was going let anyone take a swing at me without putting up a fight. So, I decided to stand my ground, told her off, exited their house, hopped into my car and headed home. 

At the time, we were cohabiting and I happened to be her ride home: a not-so-short journey taking about 80 minutes. As I was halfway through the drive, I received a pleading phone call from her, asking me to return and pick her up.

Upon my arrival, she invited me inside. However, her mother insisted that I still needed to pay for my supposed wrong actions with a beating. In disbelief, I escalated things by leaving again. Later, my girlfriend managed to get someone else to drop her off at our place. We both decided to never bring up the incident again.

However, that conversation, as bizarre and unwelcoming as it was, planted the seed for our breakup. I mentally broke up with her while they were discussing disciplining men in my presence. It took a month or two to make new living arrangements, but once that was sorted, I officially ended things with her.

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60. A Night To Remember

A while ago, when I was taking a long break and navigating a rough patch in my life, I decided to head to Colombia to pick up Spanish. One day, I was out with some friends from my language school and I noticed this incredibly beautiful woman. I could tell immediately that I needed to ask her out, even though my Spanish skills were quite basic at the time.

Without much thought, I asked her on a date, and to my delight, she said yes. The next day came—the day of our date—and I wasn't feeling my best. But, driven by excitement, I decided to push through. I went to her place, picked her up, and we ended up at a lovely restaurant. After dinner, we decided to go for a stroll on the beach—a cliché, I know, but it's true.

Suddenly, I started feeling worse, light-headed and dizzy. The inevitable happened—I found myself violently sick, throwing up with such force that I barely remember much of the ordeal. Apparently, I passed out and woke up in a hospital.

When I regained consciousness, imagine my astonishment to see my date sitting by my side, having swapped her ruined outfit for workout clothes. She was genuinely concerned for me and even said we didn't get to finish our date properly. Now, we're planning to get married this year.

The Worst Dates EverPexels

61. He Had A Temper

I remember once, I agreed to a date with a man I'd connected with on gay.com. He offered to come get me and I was perfectly alright with it. The moment we started driving, he started losing his cool with every other driver on the road, with no good reason. 

At one intense moment, he even stuck his head out the window and began shouting foul language at a poor family in a van, even though they hadn't done anything to obstruct our way. I was genuinely afraid.

These First Date Red Flags Will Have You Swiping LeftWikimedia Commons

62. Gaslighting Goober

The person I was dating had a curious habit. He'd pull out his firearms, ensuring they were safe, and pretend to shoot at me, shouting "Bang!". Each time I'd react, he'd chuckle and tease, "Imagine if the safety wasn't on—wouldn't that be something?"

The following day he'd upend things and insist there was no such incident the previous night. He had mastered the art of gaslighting. It was so profound that I began to question my own memory, as he would deny every single thing.

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63. He Got Gassed

The most disastrous date I've ever had began like any typical high school situation: a girl proposed that we hang out at her house while her parents were away for the weekend. It seemed like a great idea at the time, so I agreed. We were enjoying each other’s company, everything was running smoothly.

As the evening wore on, we found ourselves resting in her bed together. Next thing I know, she's fast asleep, deeply snoring. It's around 3 am, and I'm still wide-awake. Then, something unexpected happened...she started to stir slightly, and out of nowhere, she released a fart like I've never experienced before.

It began, and it just didn’t stop. Initially, I assumed it was her elderly pet dog. I quickly realized I was wrong. The smell hit me next; it was shockingly bad. I used my shirt as a temporary gas mask, all while thinking to myself, what on earth had she consumed earlier?

The cherry on top? She let out a small sigh of relief when the epic fart had finally ceased. That was it, I couldn't stand it any longer. As gently and quietly as I could, I put my pants, socks, and shoes back on, making sure not to wake her. 

I tiptoed out of her room, down the stairs, and straight out the front door. Fortunately, our houses were close, so it was not a long journey back home.

Unavoidably, she questioned me the next day, asking why I had left so abruptly. But I just couldn’t bring myself to explain the real reason; it would've been far too embarrassing.

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64. He Loved Radio

So, my date walked in and right away mentioned that he knew me because of my small acne scars. They're really not that noticeable. We settled down at a café, and as soon as our coffee was served, out of the blue, he leapt through a big, ground-level window. The window was low enough, so it was a fairly easy feat for him. After hitting the sidewalk, he bolted up the street.

I was left there, stunned, for what seemed like forever, unsure of whether to pay for the coffee or try to figure out what had just happened. Then, he returned. He then gave me a baffling explanation.

Turns out, he'd spotted his favorite low-rated radio personality walking by, and felt compelled to run up and express his admiration. He couldn't stop chatting about how thrilling the whole ordeal was, while I sat there completely awestruck.

These First Date Red Flags Will Have You Swiping LeftFreepik, wayhomestudio

65. Going Nowhere Fast

This girl was incredibly attractive, and she had a unique way of making her interest known. She revealed that she had been checking out my Instagram for a month before she finally decided to contact me. I brushed it aside initially, but then I had a realization. 

We had matched on Match.com two months prior, yet she never acknowledged that. I was caught off guard and we ended up sleeping together on our first date.

Following this, she wanted to visit me again the very next day. My immediate thought was, "awesome!" Maybe I was impressive. However, things felt unusual this time. She pulled back on the affection and intimacy completely. I considered it, thinking, “Maybe this is a serious relationship. I can handle it, I'm mature enough.”

Then she started visiting every day for two weeks. Before I knew it, she began leaving her things at my place, occupying my time without any reciprocation. She warned me against hurting her feelings, explaining how her ex had taken advantage of her in her sleep constantly, which left her emotionally delicate to the point of contemplating suicide.

I suggested we either deepen our relationship or take things slower. We could consider weekend dates until she was comfortable, but moving into my place wasn't an option. Unfortunately, after that encounter, she ceased contact entirely. 

I had to send all her belongings back to her parent's house, where she resides. Despite my attempts to reach out, she's avoided communicating with me ever since.

My Date Turned Out To Be PsychoPexels

66. Three’s Company

I had planned to take a girl to the cinema when she asked, "Is it cool if my best friend joins us?" I thought, "There goes my chances," but wanting to be amicable, I responded, "Absolutely, bring them along!" As it turns out, her 'best friend' was actually her ex-boyfriend.

It was a surprise reveal, apparently they had dated but managed to stay friends afterward with no spark left between them. I thought, “Well this throws a spanner in the works, but let's see what we can make of it." I decided to purchase our tickets (hers and mine), even though she was willing to pay for her own.

The curveball? Right after, she bought a ticket for her ex. The night wasn't a total disaster, we all got along, but it certainly felt like a struggle vying for her attention. Obviously, it was an uphill battle, since they had such a strong bond.

Back at home, the ex-boyfriend added me on Facebook, then warned me off dating her, claiming she was a terrible girlfriend. I managed to get her alone for another movie outing, but things just somehow didn't click. I was genuinely fond of her, but it seemed like my feelings didn't register with her. Oh well, such is life.

A word of advice for those dating in future: reconsider the cliché movie date.

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67. Free Tats

I began chatting with a tattoo artist on Facebook Messenger. He was on the brink of launching his own studio, and asked me to hang out there while he was getting things ready. I'd barely been there for ten minutes before he started asking if I'd told anyone where I was. As if this wasn't off-putting enough, things got even stranger.

He began discussing potential tattoos I might want and offered to ink one for me right there, free of charge. Then the real kicker: he told me that if I'd be his girlfriend, he'd provide all my tattoos without cost. I found an excuse to make a sharp exit. 

The whole situation was incredibly odd, especially since he was a brilliant tattoo artist. I still regret not taking advantage of the free tattoo when I had the opportunity. Plus, he was quite handsome. Had he not come off as such a weirdo right away, he might've stood a good chance of winning me over.

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68. She Cashed In And I Cashed Out

I was chatting with this girl online and we planned to go on a date together. I reached her place to pick her up, and found her approaching my car while deeply absorbed in a phone call. Getting into my car's passenger seat, she signaled to me to remain silent as she continued her emotional conversation with her estranged father.

We were still 15 minutes away from the town, and all through the journey she was engrossed in her phone conversation. Turns out, she had a secret motive—she was trying to persuade her father to lend her some money to help her out of a fix. 

She was reconciling with her dad, with whom she hadn’t conversed in over seven years, all to convince him into wiring her some funds. She briefly put him on hold to request me to pull over at the Dollar General store in town so she could purchase a Green Dot card or something like that.

Even though we hadn't properly met and conversed in person, I agreed to her request. I pulled over at the Dollar General, and she darted inside to purchase the card, all the while continuing her conversation. 

On returning to the car, still in the grip of emotions verging on tears, she provided her father with all the necessary information and even managed to cry a little for added effect. Once the card was loaded with money, she expressed her gratitude, telling him how glad she was to have him back in her life.

She told him she loved him before ending the call. The moment she hung up, her entire demeanor changed—and it was ugly. She started calling him names and expressing her true feelings, "I can't stand him". She then stowed away her phone, cheerily apologized for the awkward situation and carried on as if nothing out of the ordinary had happened.

My Date Turned Out To Be PsychoPexels

69. Clownin’ Around

"So, office work, right? But is that what you truly want to do for a living?" I inquired, "Did you get an education for this?"
"Well…” she responded, rummaging in her purse, "Funny you should ask, I'm actually attending a clown school". You wouldn't believe it, but she reached in and pulled out a bright red clown nose and popped it on.

Don't get me wrong, had it been our third date or so, I might've rolled with it. But this was date number one. We had been texting for a week, trying to impress one another. But she was pretty, and I was interested in her.

My response was, "Wow! That's unique. I had no idea clown schools even existed.”

"Oh, yes! It's pretty competitive!"

"Really? So, are you studying at clown university, clown college, or maybe a clown technical institute?"

Sadly, my joke fell flat. She perceived it as an insult. Apparently, for a clown, she missed the joke entirely.

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70. On A Scale from One To Ten: You Suck

So, I was thinking about potentially seeing a guy, right? Then he goes on and ends up telling me I'm a 7.5 out of 10, and apparently, that's being generous. 

He tried to make it sound better by saying most guys are okay with only a six for someone they'd marry. Yeah, discovering he was actually serious about this, no laughing matter, was the end of that for me.

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71. Quaking In Fear

I experienced a seizure, and when I regained consciousness, he was there looming over me, shouting with harsh words, telling me "This is embarrassing". He then forcefully pulled me to my feet, pushed me into a wall, and sternly told me to never let it happen again. 

That was the first clue he gave me that he could act like this, and immediately, I knew I needed to get away from that situation.

My Date Turned Out To Be PsychoPexels

72. Equality At Any Cost

I once went out for a single date with a man who, despite me not being physically drawn to him, seemed like a pleasant fellow. However, our entire date was awash with him gloating about his wealth. We ended up splitting a pizza. Out of the whole pie, I only ate a single slice, while he devoured six.

When it was time for the check, he made an awkward suggestion—that we split it in half "as that's the norm in today's world." As we concluded the evening and he escorted me home, he went for a kiss. But oh boy... his breath... it was as though he'd dined on roadkill.

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73. Temper, Temper

I had a first date with this dude, and it was sailing relatively smooth. I popped over to the bar to grab another drink, and the bartender jotted down a music suggestion for me on a piece of paper. When I re-joined my date, he questioned, "Did you just slip that guy your digits?" His assumption left me stunned, and I clarified that it was simply an exchange of music tips, nothing else.

Suddenly, my date flared up, warning he was about to give the bartender a piece of his mind. I couldn't help but point out his absurdly fiery temper. He nodded in agreement and shared a tale about the time road rage led him to punch his car's windscreen, leaving him with scars. That was more than enough information for me to want to hit the road.

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74. False Positive

When I attempted to end things with my girlfriend, she suddenly declared she was expecting. There were plenty of warning signs beforehand, but this really was the cherry on top. She would share photos of positive pregnancy tests, but wouldn't take any in my presence. We scheduled a doctor's appointment for confirmation, which she secretly canceled afterward.

At the same time she was pulling all this, she was also threatening self-harm. Looking back, I should've seen it coming, but I was naive and inexperienced. Later, I learned she did the same thing with her next boyfriend when he tried to break it off with her. He had her put under the Baker Act for her protection.

My Date Turned Out To Be PsychoPexels

75. Got Milk?

A while back, I joined a nursing student for coffee and he chose to share an alarming story. He vividly recounted an episode at a party where he and his ex-girlfriend somehow found themselves helping an elderly woman to use the bathroom. 

Apparently, this wasn't an isolated check on his character—he had repeated this act in previous parties, but partnering up with his girlfriend this time around.

I was horrified, and quickly found a reason to leave. The most amusing part? A few days later, he messaged me, proposing a second meet-up. I chose not to reply. Yet, the very next day, he texted again saying, "It was because of the milk story, wasn't it?"

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76. He Was Honestly Quite Scary

On our first date, we decided to have dinner at his house. All was going well with us chatting on his sofa, until he suddenly needed to use the bathroom. As he got up to leave, he casually mentioned his home was covered in security cameras and advised me "not to take anything". I was taken aback, assuming it was a joke until he freaked me out further.

He gestured towards a pile of papers on a side table, stating with an air of honesty, "That's my rap sheet. Everything is laid out there." Briefly, he left me sitting there, contemplating whether to bolt then and there. Curiosity won over and I decided to check out the papers. What I discovered was stunning.

It was an extensive record of his arrest history, covering three states and filled predominantly with domestic assault cases, interspersed with a few minor drug-related offenses.

When he came back into the room, my phone conveniently rang. I didn't recognize the number but I decided to take advantage of the situation. I pretended it was my daughter and made up an urgent reason why I needed to pick her up right away. I still have no clue who was really on the other side of that call. Regardless, I bolted from this guy's place and never turned back.

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77. I Wheeled Her Out Of My Life

My former girlfriend had intense mood swings, loving me unconditionally at times, and at others, she held baseless grudges against me. What finally ended our relationship wasn't particularly dramatic, but it was nonsensical. 

One day, she phoned me up early in the morning, around 6:45 am, complaining about how someone criticized her for parking half-in-half-out of a handicapped space.

My response was simple, "You know you could potentially get a $200 fine for blocking an accessibility parking space." Surprisingly, she reacted by accusing me, "YOU ALWAYS SUPPORT OTHER PEOPLE. You despise me. You might as well be the chairperson of the '[her name] Haters' club. I cannot talk to you about my job anymore."

Her overreaction was simply because I cautioned her about the consequences of obstructing a handicapped parking space. Needless to say, after this episode, I ended the relationship within a few minutes, as this wasn't the first irrational incident.

My Date Turned Out To Be PsychoPexels

78. An Awkward Introduction

I was left hanging at a coffee shop when she rang me about an unexpected situation, meaning she couldn't come. I was there for just a few minutes and wasn't too bothered by it, so I thought I'd check in with a buddy of mine.

Eventually, I met him at a pub on the other side of town where he was unwinding. Interestingly, it was there he presented me to a woman he'd just connected with over a game of pool. Could this be a potential date?

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79. Her Dance Card Was Full

I once went on a blind date with a lady who seemed to be dealing with some mental troubles. When I arrived at her house to pick her up and we spent some time in her living room before heading out for dinner, she only talked about her ex-boyfriend who tragically died in a car crash two years prior. He was reportedly speeding and intoxicated at the time of the accident.

Things took a ghastly turn after our conversation when she momentarily left the room. She returned with an item that formerly belonged to her ex, something she'd kept as a keepsake. I was shocked to discover it was a book splattered with blood from the day of his accident, which was quite eerie. Regardless of this alarming sign, I chose to continue the date.

At the restaurant, we chatted while savoring our meal. We were about halfway through when we decided to take a break for a dance. When we got back to our table, an unknown guy asked her to dance. She accepted, much to my surprise, but I remained cool about it.

An hour later, she was still dancing and hadn't returned, so I chose to leave. It seemed she was enjoying herself more with him, so I figured he could take her home. I suspected it took a while for her to realize I'd left. In reflection, I could have handled the situation better. Regrettably, I find myself thinking quite often, "I could have done better."

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80. Power Hungry

One time, we had a discussion about children and his desire to have them, while I absolutely didn't. He admitted he wanted to become a parent because he craved the adoration and absolute authority kids usually have for their folks. He also loved the naivety of young children.

He mentioned that he looked forward to bending reality for his future offspring, and he was excited about feeding them tall tales for his amusement. He relished the idea of wielding that extent of influence and dominance over others. 

But the most twisted and unsettling part? His only motivation to have children was to manipulate their innocent minds. Our relationship ended, and now, he's a married man with two kids.

My Date Turned Out To Be PsychoPexels

81. An Icy Encounter

During my university days, a girl I was smitten with invited me to an ice skating session with some of her pals. Now, being an ice skating novice who was slow to grasp it, I was determined to make a good impression. The sad reality was that I spent most of the time clinging to the walls and making a spectacle of myself.

The cherry on top of this embarrassment sundae happened when I took a tumble in front of a crowd just as someone snapped a photo. As luck would have it, my stumble was captured for posterity, making my faux pas unforgettable. Following this debacle, she brought me back to my dorm and effectively ended any potential romance between us. But, trust me, there's a silver lining to this tale.

My current wife was present at that rink on that ill-fated night. Awareness of this didn't come until a couple years into our relationship, when she suddenly identified me as 'the guy who couldn't ice skate' and pointed out that my erstwhile date wasn't exactly smitten with me.

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82. She Had Two Choices

This occurred during my college years. I found myself hanging out with this dude in a state park after dark— yes, I realize it wasn't the best idea. Everything was going fine until he abruptly asked, "Do you ever get the urge to harm people in seriously awful ways?" Picture being alone with a guy in the middle of a deserted park at night and hearing that. Scary stuff!

So, naturally, I had the sudden urge to get as far away from this dude as possible. But there was a major hitch: I had no clue how to get back to my dorm. When I asked him for guidance, he refused. He told me I could either find my way back on my own or stick around with him in the forest. He even snagged my phone to prevent me from using the Maps app.

I'm amazed at how trusting I can be when it comes to someone I'm into. I'm truly relieved nothing worse happened.

These First Date Red Flags Will Have You Swiping LeftFlickr, Ben Schumin

83. Post To Post

When I was much younger and naive, my boyfriend began publicizing all my personal details on the internet. This included my full name, address, and lots of other sensitive data that anyone could access. As if that wasn't bad enough, he then escalated things by sending me images and videos of him inflicting self-harm and consuming entire pill bottles.

That was the moment I realized I had to distance myself from him.

My Date Turned Out To Be PsychoPexels

84. Bragging Rights

During our second outing, he boasted about a few things: 1) His ability to remain jobless on unemployment benefits for a long period, 2) His skill in persuading his mother to allow him back home after being kicked out, and 3) His contribution towards a $3,000 bill for a dancer's implants, despite not getting anything in return. Oh, but it gets worse.

He also admitted to getting into some legal trouble as he was arrested for threatening teenagers, even though he claimed he had no intention of actually using it. This fact he seemed to half-brag about, not fully. It was weird because he came off as such a nice fellow during our initial outing.

With all that shared during our second date, I couldn't help chuckling internally and pondering on how to wrap up the date gracefully. Thankfully, it wasn’t an issue as he had to dash off after dinner to join his pals at the video store.

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85. Stamp Of Disapproval

A while back, I had my first date with someone I'd met online, and we decided to meet at a local bar. The bartender was asking everyone for ID due to some ongoing compliance checks in the area. I handed over my ID without any fuss, while my date seemed a bit irritable about the whole thing. My ID was quickly checked and returned, no problem.

However, when the bartender checked my date's ID, he laid it out on the bar counter right in front of me instead of handing it back directly. I managed to get a peek and felt a chill run through me—the ID bore a stamp for an "intimate" offender, a mark used in my state. 

The look on the guy's face when he picked it up, glanced at the bartender, and then me was telling. He abruptly left, and I wasted no time in looking him up online.

Lo and behold, he was on the offender register and had spent time in jail. That was a wake-up call for me—always do a Google search. And the bartender? Well, we've stayed good friends since that day.

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86. Long Distance Looney

I used to be in a relationship where we lived pretty far apart. My girlfriend had a rule; no naughty videos allowed. She felt so strongly about it that she even made me put in software that enabled her to remotely check my computer from time to time. She wanted to be sure I wasn't sneaking around watching anything behind her back.

This didn't just end with my computer, it also spilled over onto my social media. She would occasionally log into my Facebook account and go through my messages, just to see if I was being unfaithful. I couldn't be happier that I've moved on from that.

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87. Laying All Her Cards On The Table

You want to hear about my most challenging date? The girl I was with had Crohn's disease. Midway through our dinner, she pulls out her urine bag to show me, saying that I should know what I am signing up for. The tube from the bag accidentally upsets her beverage. It's a serious disaster. But I really felt for her.

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88. Showing Off His Creepy Side

One time, I found myself in a club, and my memory of the night went a bit fuzzy. I vaguely remembered talking to this guy in a suit. The next morning, I received a text from this mystery man, Willis. As fate would have it, neither of us had a clear recollection of the other. Nevertheless, we struck up a friendly conversation over messages, and we both thought it'd be a laugh to hang out.

Lunch was in order, so we met up. But right off the bat, I thought this guy was a bit too awkward and showy. Still, he seemed kind-hearted, so we grabbed a pizza and started chatting.

As I'm training in public policy, I mentioned it. I was pleasantly surprised when he asked what specific policy area I was interested in—people usually don't bother. I found myself passionately talking about my desire to improve education because I believed in its transformative power, especially for those from less privileged backgrounds.

Once my eager spiel came to an end, he made a horrible remark: "Interesting, but I don't think education should be for low-income folks. When I grow older, I'll need maids, butlers and all. Someone's got to do those jobs.” Taken aback, I responded, "Well, some do share that perspective," starting to think about how I could wrap up this date. Little did I know, the worst was still on the horizon.

We finished our pizzas, and I made up a story to make an early exit. He questioned my need to leave and said, "I should just end your life and keep you with me”. Very charming of him. I told him that's not something to jest about. But he retorted, "I would bury you right there, haha”.

Needless to say, I flagged a cab shortly after that.

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89. Momma’s Boy

So, on our first date, he decided to take me for a meal at his mom's place...where his brother and the mom's eccentric roommate were also hanging out. Following our meal, we decided to catch Iron Chef altogether, seated on the floor since there weren't enough chairs to go around. Interestingly, during the show, his mom decided it would be a good time to discuss utilizing vibrating gadgets while doing household chores to make the tasks more interesting.

Now for the real kicker: He didn't even stay with his mom. Not surprisingly, this turned out to be our first and last date.

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90. I Made A Quick Departure

After my flight landed in Boston, I found a whole slew of text messages waiting for me on my phone. The text tone started with a friendly "Hey" and escalated alarmingly to a very intense "WHERE ARE YOU! DO NOT IGNORE ME!"

My reply was something like, "Hey, remember when you dropped me off at O'Hare airport just THREE HOURS AGO?" We hadn't been dating for very long, but I'd noticed a few warning signs. This episode was the glaring red flag that convinced me it was time to end things.

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91. Musical Urinals

We caught a flick together. Preoccupied with the plot, she excused herself for a bathroom break. Not wanting her to feel abandoned, I decided to take my bathroom break too, with a plan to promptly get back before she did; I just didn't want her to come back to empty seats. She beat me back, and I didn't think twice about it at the time.

After the movie, we relaxed at her place for a while. Leaving her with a goodnight kiss, I headed home, convinced that our date went smoothly. However, a week of her not answering my calls raised some doubt. Eager for answers, I turned to the friend who initially introduced us, questioning what was going wrong.

She filled me in on the uncomfortable detail: in my hurry, I had unknowingly entered the ladies' restroom. As fate would have it, we ended up peeing in adjacent stalls, and it clicked for her when she noticed my boots. Seemingly such an enormous red flag for her, I couldn't really fault her reasoning.

When I managed to reach her finally, with a thorough explanation ready to unroll, she broke the news to me: she was moving to Turkey, intending to reconnect with her former love interest.

Worst Thing Done on a Date FactsMax Pixel

92.  Scene And Heard

I had to catch a bus that was a mile away from the university's entrance. I intended to break up with my girlfriend in a public space to avoid any significant drama, but it completely backfired. Rather than staying calm, she made a big spectacle, begging me to stay and causing a scene in front of a crowd of about 30 people.

The drama didn't stop when I reached the bus stop. She made an attempt to shove me in front of a moving bus. In disbelief, I shouted at her, "Are you trying to end my life?" She fired back, "I might if you won't stay with me." Not stopping there, she invaded my home and plastered it with our pictures.

Later on, she bombarded me with phone calls, threatening to end her life. She even went as far as trying to seduce my friends and ended up kissing my former best friend.

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93. The Ole Switcheroo

My most awful date began like a romantic night out, but it turned into a sales pitch for a multi-level marketing scheme. On a positive note, I still use the Cutco scissors I got and they're pretty good.

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94. Outed!

I hung around the theater, waiting for her arrival for a solid two hours. When she finally turned up, she was under the influence. Rather than planning, we committed to the first movie that was about to roll, which unfortunately turned out to be dreadful. After the movie, she suggested hitting up a bar. 

It became evident quickly that it was a gay bar, and she started nudging me to come out as being gay. To try and salvage what was left of the evening, I engaged in some light-hearted banter with the gay bartender.

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95. Eat And Run

One evening, I decided to grab a meal at Buffalo Wild Wings with some buddies and let my girlfriend know. To my surprise, a few of her pals showed up and took a table close to ours, but they didn't order any food. They just sipped on water, casting occasional glances in our direction.

After we finished our meal, we headed towards the parking lot, only to find my girlfriend's car there. I noticed her car seat was fully reclined, barely spotting her trying to stay out of sight in the driver's seat. That seemed a bit odd to me, and we decided it was time to leave.

No sooner had we reversed our car than she did the same, trailing us all the way through the car park. I texted her, questioning this unusual behavior, but she kept insisting she was just hanging out with her mom. This strange incident marked the end of our relationship pretty soon afterwards.

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96. The Stench Of Success

It was our third date, this time we picked a Poison-Def Leppard concert. Before the show, we didn't have a meal so I was famished. I quickly got a chicken salad sandwich from a service station before I went to collect her.

In the middle of the concert, I suddenly needed the restroom. When I reached the toilets, they were in a sorry state. Since we had VIP tickets, I decided to hold on and use the VIP restroom on our way out. Let's just say that my visit to the restroom caused quite the stir, redolent enough to have five guys commenting. This, admittedly, made me smirk.

We had the car parked out front, so we retrieved it and sat waiting. Suddenly, the urge hit me again—and this time it was more urgent. I was getting stomach cramps every 2-3 minutes, all the while gripping the steering wheel with all my strength and perspiring heavily.

Then, thinking that a small release of gas could alleviate the discomfort, I tried. Regrettably, it resulted in a mess in my pants. I rushed into the nearby woods to finish relieving myself and in the absence of anything better, used my tank top for clean-up.

Fast forward to the present, we've been happily married for 12 years and have three kids.

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97. Eating For Two

I got talking with a girl online, and after a little while, we seemed to hit it off, so we planned to meet. I suggested we should go out for dinner, maybe get drinks later if everything went fine. Long story short, her picture didn't exactly match her reality. She justified it by saying that her crazy ex was bothering her, so she used her sister's image and name.

Yep, you heard it right – her NAME! She told a fib about her own name! During our chat, I discovered that she was an only child. She didn’t seem to notice her mistake, but I certainly did. She kept talking about various topics that frankly, I was not at all interested in. When the meals arrived, I was stunned. She didn't bother using cutlery, and practically devoured her food.

You should know we were at a steak joint. Yes, she picked up her steak and dug in using just her hands. The less said about the potatoes, the better. It was the most dreadful date I've ever been on. I reached the point where I couldn't stomach my meal. So, I told her I wasn't feeling great and requested a take-out box for my dinner. Her reaction? She asked if she could have it!

She then heartily tucked into my meal. The server appeared and asked her when her baby was due. She casually responded that she was two months away from the due date. I was dumbfounded! Not only by the audacity of the question but equally by her unexpected answer. Nonetheless, being the gentleman, I paid the bill since it wasn't going to pay itself. Polite as ever, I said a simple "nice to meet you," got in my car, and headed to the bar. But, there was a twist. She followed me.

Once she saw me at the bar, she began reprimanding me for choosing to go out instead of calling it a night. Now I was labelled a liar in my regular bar's parking lot, with my co-workers starting to trickle in. I never could live it down. I had enough and decided to bolt. Jumping in my car, I sped off home.

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98.  I Relieved Him Of His Duty

I used to be married to a very unstable man. He once proclaimed he was headed to the forest to end his own life. Concerned, I quickly alerted the police, fearing he was undergoing a PTSD breakdown from his supposed time in the military. They intercepted him, confiscated his weapon, and shockingly revealed to me that he had NEVER SERVED IN THE MILITARY.

This came to light four years into our marriage. I gathered photos of the damage he had done to our home and successfully obtained both a restraining order and a divorce. Courts frown upon using stolen valor as an excuse for violent behavior and emotional abuse. To my dismay, he repeated this behavior with his second wife, who ended up divorcing him as well.

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99. Showing Off His Creepy Side

Once, while at a nightclub, I blacked out briefly and met a gentleman in a suit. The next morning, I received a message from Willis, the suave suited guy. Neither of us could quite remember the other, yet through texts, we found each other quite likable. We decided it'd be an amusing adventure to go for a date.

We rendezvoused for a lunch date, but I was immediately doubtful about a potential second date. His demeanor felt somewhat clumsy and he seemed to overcompensate. Regardless, he came off as a pleasant guy. So, there we were, sitting for pizza and discovering each other.

As I revealed my interest in studying public policy, I was brimming over with joy when he inquired about my preferred policy type (which people rarely do). I enthusiastically expressed my passion for improving education policies, believing that they could substantially transform lives, particularly for those less privileged.

After my fervor subsided, he said, "Interesting, but I don't agree with the idea of education for the underprivileged because when I'm older, I'll need maids, butlers, and such. So, someone needs to do those jobs." I replied, "That's one perspective," and began thinking of ways to wrap up the date early. Little did I know, the most startling part was yet to unfold.

After we ate, I came up with a reason to depart an hour ahead of schedule. He questioned my early exit and blurted, "I could just murder you and keep you by my side". Smooth. I cautioned him against making such jokes. He hit back with a creepy, "I would bury you right there haha".

Subsequently, I flagged down a taxi.

The Worst Dates EverShutterstock

100. Hung Up On Her Ex

On our way back home from a date, on the train, something caught my attention. I glanced her way and couldn't believe what I saw.

She was in the process of accessing her ex-boyfriend's Facebook account. I curiously asked her about her actions, to which she candidly admitted she was indeed entering her ex-boyfriend's Facebook account. Her outrageous reasoning? "I just want to make sure he's doing alright. He never bothered to change his password."

Her brief check soon turned into a deep dive into his statuses and personal messages. I questioned why she couldn't just view his profile without logging in, only to discover he had blocked her. I suggested she contact him through text if she was so worried, but it turns out, she was blocked there too.

Several more questions floated around my mind, but she seemed to get annoyed and defensive. Getting into an argument on what was still to be a long train ride home didn't seem ideal, so I dropped it.

My Date Turned Out To Be PsychoPexels

101. Just Pop A Squat

I was in France, enjoying a great meal at a cosy café on the street, with a woman I had met just the day before. But right in the middle of our meal, she did something totally unexpected. Without hesitation, she requested to use the washroom, stood up, took a few steps away, squatted, and suddenly, she was urinating right there in the roadside drain. I thought to myself, "Yeah, there's no way we're having a second date after this."

The Worst Dates EverShutterstock

102. Bait And Switch

After she replied to my Tinder "Hi" with something along the lines of "Hey there, fancy coming over to my parents' place?" we exchanged casual chat. She made it clear she wasn't interested in anything serious; instead, she wanted me to pick her up, treat her to dinner, and potentially have some fun afterwards. It felt very calculated, which was off-putting, but I figured, heck, she's attractive.

I searched for the location she provided and a wave of discomfort washed over me as I recognized it. Oddly enough, the address led to a neighborhood I'd done work in, a house specifically that I knew was on the market. The owner had recently passed and his children were refurbishing the place for resale. 

Seeing this, I was practically certain I'd walked into a scheme, but driven by curiosity, I decided to drive past the place to see if anyone was actually there.

I messaged her that I was on my way, but intentionally didn't mention I'd be turning up in a different car. The neighborhood was luxurious, perched on a sea cliff, and the situation felt oddly adventurous. I went there in my work truck. 

As I drove past, a massive guy emerged from the house, scrutinized my truck, and then disappeared back inside. I noticed other people were there too. I quickly got out of there. I was pretty sure this was either a plan to rob me or a cruel prank. Either way, I wasn't keen on sticking around to discover the truth.

Horrible datesShutterstock

103. Valentine’s Lost

My mom's worked as a server for over two decades, spending many Valentine's Days serving tableside. She's experienced an ample amount of sorrowful moments. The ones taking the hardest hit are the elderly gentlemen and ladies, who dine solo due to losing a spouse. They often sit there teary-eyed. My mom takes time out to console them and showers them with hugs.

I'm seriously in need of a bathroom break.

Waiter's ValentinesPexels

104. A Relaxing Vacation

I crossed paths with this guy and we instantly clicked. We started hanging out within a day or two. This guy was like a breath of fresh air and it was hard not to think, "At last! A genuine man". Then one day, he proposed: "I know a place where we can spend the weekend, if you're up for it". It seemed like a great idea. But once we arrived, he realized he'd forgotten his key... so out came a crowbar.

This freaked me out, so I wanted to know whose house we were stepping into. He assured me it was his father's vacation house and that he definitely had the permission to be there. I brushed off my suspicion, thinking I was merely overreacting. For the next four days, we stayed there without any hassles.

I made myself comfortable in the master bedroom, took showers there, prepared meals in the kitchen—you name it. But as we were about to leave, the guy said, "Look what I found". He showed me some jewelry and credit cards that belonged to the house. Panic started to set in. As gullible as I was, I thought the house belonged to his father and he was just having a moment of defiance.

When he confessed the truth, it hit me. I'd unwittingly aided him in a burglary. The house wasn't his father's; rather, it was his mother's ex-boyfriend's. Needless to say, they did NOT authorize us to be there. His stepfather even had a restraining order against him due to a similar incident a few years back.

Fast forward to a few weeks later—I got stopped by the police and taken out of my car because I was implicated in this mess, given that the owners had rightly pressed charges. I narrowly escaped a serious sentence.

Creepy Moments FactsShutterstockSources: , , ,


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