Dates Gone Terribly Wrong

January 4, 2023 | Mae Stanley

Dates Gone Terribly Wrong

Dating can be an incredibly tumultuous endeavor that leaves one or both parties heartbroken. These brave Redditors shared their sordid tales of love and lust, and unfortunately, only a few of them made it out unscathed. If you're single and looking to get into the dating scene, consider their stories a warning of the horrors that can arise:

1. Change Of Plans

So, after chatting with this person for a few weeks, we decided to meet for a coffee downtown. But the thing is, she looked nothing like her pics when she showed up. I shrugged it off thinking people usually sugar-coat their photos. Then things got really weird.

She asked about my plans for the next weekend and I mentioned a camping trip with my buddies. She wanted to come along, but I was like "Uh, we just met". She freaked out, acting like we were an old couple or something, and tried to guilt me for not inviting her. Even after the drama, for some reason, I stuck around.

She wouldn't drop the camping topic. She kept asking where we'd be setting up camp. I gave her a vague idea of where, and she goes "Cool, see you there". I told her again I wasn't comfortable inviting her, and she played it off like, "I'm showing up anyway. You won't see me coming". She even gave a creepy laugh. That's when I'd had enough. I left some cash for my coffee and bounced outta there.


2. Three’s Company

I found a girl on Craigslist and we planned to meet at a city-center bar. To my surprise, she was already there when I arrived...with a male friend. I put it down to safety and went to join them. I regretted it almost instantly. There was no room at their table but the bar was jammed, so I bought a drink and stood.

But they pretty much ignored me, not responding even when I tried to join their chat. I didn't get more than a 'yes' or 'no' even when I directly spoke to them. Finally, I finished my drink, paid my share and left without a goodbye. Later, she bombarded me with messages, calling me terrible for not paying their bill.

Nightmare FamiliesShutterstock

3. Small Town Woes

I was using a dating app in a not-so-big town and had been on a few dull dates. Then, I matched with a girl who caught my interest. Something felt strange about her the whole time, particularly how super excited she was to meet up. I ended up at Starbucks, waiting inside for about 20 minutes past our planned time.

She texted to say she was late and asked me to wait outside so she could spot me when she drove by. That's when I noticed another guy, phone in hand, on the sidewalk. We knew each other from the gym so I asked if he was waiting for a date too. And guess what? The same chick had tricked us both as payback for dating the same girl in the past.

Dealbreaker DatesShutterstock

4. The Sound Of Silence

So, on our date to Dave and Buster's, I could tell she was kinda off. I tried sparking a convo with her, but all I got were one word answers or an "I don’t know," even when I asked her about herself. After about five awkward minutes of silence, she finally stirred.

She went off to the bathroom and when she came back, I straight up told her, "Look, if you’re not feeling it, feel free to bounce. No hard feelings". Then things went from bad to worse. She was pretty ticked off at what I said and packed up to leave. I said, "If you’re having fun, I’d love to stick around, but we’re not really vibing right now".

So she left and I decided to hang out a bit longer with another drink, watching the game before heading out. Later, she texted me pretty annoyed that I'd suggested she could leave if she wanted. I simply texted back, “I tried chatting with you for 15 minutes and got nothing". Apparently, she sometimes doesn’t want to talk and thought I was harsh for not being cool with that.

Worst Blind Date FactsShutterstock


5. A Quick End

I plopped down, and he was all, "Wow, you're hotter than your pics, you're my girl now." He was pretty intense. I thought maybe he was just excited or had a quirky sense of humor. I planned to stay for a drink or two, just to see what happens. I even offered to buy the first round, partly to get a breather from the table.

I cracked a joke with the bartender, got a laugh, and when I got back, my date blew up. He was yelling, pounding on the table, demanding to know what I said to the bartender and if I thought he was cute or not. He got jealous over the bartender only five minutes after meeting me.

Hotel HorrorsShutterstock

6. Miscommunication?

There was this dude I liked back in high school, and my friend kept encouraging me to chat him up. Finally worked up the courage to ask him out, and guess what? He seemed to like me too. We used to chat a lot and even swapped notes in the hallway. Then he asked me to homecoming. I was over the moon and even got a new dress!

But then came the football game, and man did things go downhill! Spotting my crush in the stands, I told him I was gonna sit with him. But he said no - and wanna know the reason why? Turns out he was there with his girlfriend. It was a huge bummer and just totally humiliating.

Teenage boy high school football players lifting celebrating, cheering teammate on football fieldGetty Images

7. Why Did He Even Come Over?

I invited this Tinder guy over because he seemed like a cool dude and we had loads in common. He wasn't bad looking in his photos, so I figured why not. Backstory - I had just settled into my new apartment with nothing but a table and a few chairs. His first weirdo alarm was asking why I didn't have any guest slippers.

I shrugged it off, thinking maybe he's used to a posh life (and he wasn't shy about admitting it). I told him no slippers, but he didn’t make a big deal about it. We headed to my balcony where he spent what felt like forever whining about his ex and how much he missed her. I just played along, but it was super awkward.

Eventually we went back inside, and he jumped into an interrogation about my lack of stuff. "No TV? No couch?" When I said I was too short on cash to go all out on furniture, he turned snooty and kept picking on every little thing.

Nightmare ExesPexels

8. Maybe She’s A Werewolf

So, I finally got this cute classmate to go out with me. I never could have predicted how terribly it went. We were at college in Wisconsin, it was January, freezing cold. I was driving us to dinner when suddenly, she unbuckles, flings open the car door, jumps straight into a pile of snow, and bolts into the forest!

I had to chase her down and plead with her to get back in the car before the cold got to her feet. We didn't go out again, but I did touch base with her now and then.

Scariest ExperiencesShutterstock

9. #BadDate

My date was mad because I wanted to bail on her, seeing as she only fiddled with her phone and took selfies with the coffee I got her. Later on, I looked through her Instagram (she asked me to follow and like her pics), and I saw a picture from our date. The caption was wild: it said, "Spoiled myself #blessed #soyummy #java". That's it.

Worst Blind Date FactsShutterstock


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10. A Whole Mess

After a biking trip back home, she had a bad fall and broke her neck. I quickly took her to my hospital's emergency room where she was admitted to the ICU and fitted with a halo. That's where I met her family. We dated for nine months after the incident, then she unexpectedly cut me off. I had no clue what was coming next: Out of nowhere, I was hit with a lawsuit worth a million bucks for her injury.

The case dragged on, even going to trial. Then I found out she had been lying - she was actually married when we were dating. Even worse, she stopped talking to me because she was cheating with another guy and was pregnant with his child during that time. He even spoke at the trial about her disability.

Heartbreaking HospitalShutterstock


11. At Least She Didn’t Feel Awkward

In high school, I once dated a friend of a friend. We watched a movie then grabbed dinner, but I was super nervous making it awkward, so it kinda fizzled out. Though we never had a second date, that wasn't the worst part. About a month later, I ended up at the same party she was attending - thanks to our common friend.

I spotted her there and thought, "Oh, this might be awkward." But an hour into the party, while I was near our mutual friend, she approached us. Soon, the same girl I had a not-so-great date with...introduced herself to me.

Meet The Parents FactsShutterstock

12. Truth Is Subjective

So, I invited this chick from Tinder over after some hot chat (mostly her doing the talking). When she got to my place, she basically ignored me. I mean, she barely even muttered a one-word reply to any of my questions–I felt like I was bothering her or something.

Every time I tried to make a move, she shut me down, right there on the spot. This went on for hours, so I just decided to put on Netflix. That turned out to be a huge mistake. Randomly, she got on top of me and started to make out–way too intensely. It was so gross–she hadn't even brushed her teeth and I could taste her leftovers.

I couldn't do it and after a super awkward drive back to her place, I was done. But the weirdest part is, before I could even leave her driveway, she texted me saying she had a great time and wanted to hang out again. But, yeah, that wasn't going to happen.

Most Embarrassing MomentsShutterstock

13. You’re As Old As You Feel

I had a date with a Bumble guy. We planned for him to pick me up for dinner at a local spot. It snowed the night before, and the roads were icy. I wanted to reschedule, but he didn't want to. When he came to pick me up, he slid on the ice and we ended up hitting a car.

Luckily, we were all fine. I was pretty freaked out, but we still went to dinner. The rest of the night was pretty chill. His insurance called me the next Monday, asking about the accident. After a long chat with the adjustor, I called him and said I didn't want to be involved anymore, but he asked me out again.

And the craziest part? I said yes. And he stood me up. He blamed it on his "old age", even though he's only 27.

Amazing Coincidences factsShutterstock

14. You’re Focused On The Wrong Thing

My date called at 2 am, super hyped for our meetup. In the middle of our chat, she wrecked her car. I didn't hear from her till the date, so I had to play chauffeur since she'd totaled hers. Started pretty decent with fancy sushi, but she didn't touch one bit—chattering non-stop instead.

Realized that she'd been pulling an all-nighter for days, her eyeballs just rolling around. Paid the bill and dropped her off to a super snooty roommate. I'm about to hit the road when her shriek pierces the air, "Where's my goodnight kiss?!" Panic hit me, I made a dash for my car. Peeped back and she's chasing me down, going full Banshee.

Folks from her apartment block watched the spectacle from their windows but I somehow managed to bail. Fast-forward a few months and I run into the roommate who remembers me as the sushi hog!

Creepy DatesShutterstock

15. It’s Too Much

I met a guy, Ron, on OkCupid. Despite being older than he claimed, he seemed decent, so we chatted on the phone before deciding to meet in person. I told him upfront nothing intimate would happen on our first meet, and he agreed.

We hung out at his place, chatted for a bit, and watched a movie. But then things started to get weird. He started touching me, which I'd clearly said wasn't on the cards. He couldn't resist giving me "compliments", even though it felt smothering. I tried setting boundaries, but he ignored me, pushing his wants on me instead - like offering me a house key and suggesting I walk his future dog.

He even tried to sweet-talk me into a planned Hawaii trip. I found him overbearing and told him so. But I agreed to meet him again, despite better judgment - but this time, he was even worse. When he started touching me again, I had to move away to avoid his hands. I eventually left his house, but he made it difficult, refusing to let go of me in a hug and blocking my car door.

He only moved when I screamed at him. Back home, I received more text messages from him, romanticising our encounters and pouring out his "emotions". I chose to ignore them. His tone eventually turned bitter, but I continued to ignore him.

The next day, I reported him to my workplace security and showed them his messages. They were shocked. All in all, Ron turned out to be a harsh lesson learned.

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16. What Did I Say?

I got to know this girl through a friend at a party, and we started hanging out. One weekend, we ended up at a hotel, just chillin' and having a good time. Our last evening was pretty normal...until she just flipped the script mid-conversation.

It wasn't a typical topic change either but like she was talking to someone else. It happened more than once. On the third time, I had to call her on it because it freaked me the heck out. She got really scared, thinking she was losing it. I did my best to calm her down and we eventually fell asleep.

Later, I found out she had bipolar disorder. We didn't really hang out again after that weird night.

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17. Strongly Opinionated

I had a date with this girl who suggested a restaurant, but it turned out to be closed. She mentioned it was the same place she held her wedding reception for her much older ex-husband. At our next stop, she showed her true self. She asked me for my opinion on Trump but then proceeded to tell me how fantastic she thought he was - before I even had a say.

She pretty much drank our entire wine order, openly said offensive things, and kept bringing up how she earned more than me (not sure if true, but certainly weird either way). She conveniently 'forgot' my name twice and spent the whole car ride back to her house trying to convince me that Obama's birth certificate was fake.

Dealbreaker DatesShutterstock

18. Older, Not Wiser

So when I was 18, I signed up for Plenty of Fish and got tricked into meeting up with a dude way older than me. We met at Starbucks and instantly, I knew I was in over my head. But I didn't know how to handle the situation, so I just went with it — worst idea ever.

The guy kept asking me my likes and dislikes only to mock them later on. Like, he would say, "So you like Harry Potter, huh? Isn't that a bit childish?"

I knew I had to escape but he just kept pressuring me to come over to his place, and even made me feel guilty by reminding me that he had paid for my coffee. I agreed to go to a park but made it clear, that's as far as I would go. I also told him we'd need to take separate cars 'cause I had plans later. While driving to the park, I called up a friend and asked her to ring me in about 15 minutes so I’d have an excuse to leave.

Over at the park, the guy brought up the huge age difference and figured that must be why I was acting "weird". He couldn't understand why I didn't want to visit his place. According to him, he only invited me over because he felt our connection was real and was worried I wouldn't want to meet him if he told me he didn't quite look like his profile pic anymore. A few moments after my friend’s planned call, the guy turned really cold and it was honestly kinda freaky.

Thank god I managed to get away after a super awkward hug.

Creepy DatesShutterstock

19. The Divine Plan

So I met this guy online and we went out on a date. Our phone chats were nice, so I figured I'd give it a shot. We decided to meet at the mall. Right from the start, something felt off about him. He then began to tell me about the amount of kids he wanted us to have, and his views on discipline were a bit extreme, saying he'd hit them if they acted up. He seriously said it was "God's wish".

At the end of the date, he trailed me to my car. Good thing it was broad daylight, the mall was bustling, and a security guard was eyeing everything. He tried to kiss me, but I pushed him away and left there as quickly as I could.

Drivers Share Their Craziest Experiences On The Road

20. The Wrong Film

So, there was this attractive and intriguing dude and I thought, "why not invite him over for a chill evening?" He swung by and everything was peachy—turns out we had loads in common, especially when it came to movies. So, we decided to watch one. After a bit of pondering, Nymphomaniac was our pick, a film neither of us knew much about. Boy, were we in for a shock.

Turns out, the movie was super disturbing and made for some really awkward, cringe-worthy viewing. It completely tanked the vibe. After enduring till the end, we decidedly agreed it was time to call it a day. Needless to say, there wasn't another date in the cards.

Embarrassing datesPexels

21. Oldest Trick In The Book

I was the first one at the restaurant, just chilling outside, when he rocked up, bouncing off the walls. We got to our table, and I could tell he was on something. We grabbed a drink there before heading off for dinner elsewhere.

During drinks, he said he could hook me up with a car sales job at his place and wanted me to move in – just to piss off his ex. I laughed it off but agreed to meet him at the next spot. Then he did something that really scared me – he followed me back to my car and jumped in the passenger seat, wanting a ride.

Freaked, but trying to play it cool, we arrived at the restaurant, but I was well and truly spooked. I pulled the old 'bathroom break' card to escape, but I had left my purse at the table. So, I enlisted the help of the hostess to get me out of this disaster date. Fast forward ten minutes and one wine glass later.

The manager was doing the rounds, dropped by our table, and said I had a call waiting. Cheesy, but it worked. I told him I'd be back in a second, grabbed my bag, and sprinted out of there.

Unforgettable Customer Service MomentsShutterstock

22. It’s Shark Week Every Week

She was totally into sharks; shark stickers on her car, shark ink on her skin, wouldn't shut up about them. After the meal, she confessed being broke, leaving the check to me. I mean, I planned on paying anyway, but assuming I'd cover it without heads up was kinda rude.

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23. Multi-Level Madness

We grabbed coffee together. Straight away, he whipped out these Amway brochures and started ranting about the company and its products. He was all about the perks of being a sales rep - events, goodies, you name it. Seriously sucked thinking I'd been tricked into an MLM thing, and I called him out on it.

That sent him into a total meltdown. He got mad and defensive, saying he wasn't recruiting me! Like, cause I'm from Michigan and that's where Amway started? Yeah, right. So, I was done and asked for the bill. The guy straight up yells, "SEPARATE CHECKS!" Everyone turns to stare. Super awkward.

Now, I'm feeling kinda uneasy. The dude looked ready to explode and I was worried he'd follow me. Once we got outside, I stayed close to the café, hoping he'd go off to his car. But no, he used that chance to start screaming at me right there in the parking lot.

He kept on insisting he didn't try to recruit me, blaming me for ruining the date. Like his car park shouting match was going to make me change my mind? Nuh-uh. I couldn't take it, ran to my car, locked up, and drove around aimlessly before heading home.

Waiters Witnessed Disastrous DatesShutterstock

24. If The Shoe Fits…

So I was part of this odd "Cinderella" game in college where girls would chuck a shoe into a pile, and then guys would pick a shoe, and whoever's shoe they got was their date for the night. My roomies and I got in on it for a laugh. But, of all people, the weirdest dude chose my shoe. Sticking to the plan, I went on the date that took place at a bowling alley.

He would legit scream "THAT'S MY DATE!" every time I got up to bowl, super embarrassing. He'd also hurl the bowling ball like he was in shot put, probably damaging the lanes. His toss was so off that his ball would sometimes roll down someone else's lane. He even tried to plant a kiss on me right there in front of everyone... It was awful.

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25. Just Make A Decision

I connected with a girl on Bumble and we chatted for some weeks. We decided to meet up one weekend. The day before, I checked in to see if we were still good to go. She didn't reply until the day itself, saying she had plans later but suggested a coffee catch-up beforehand.

She asked for a lift as her car was in the garage. Like a dope, I agreed. When asked for coffee spot suggestions, I suggested Starbucks in my area, but she wanted a different choice. Using Google, I found a cool local café and threw the idea her way.

After her 45-minute silence, I followed up, to which she agreed but mentioned the café would be closing in 20 minutes. Back to Google, I found another café in her area that was open for the next two hours. When I suggested that, she asked for a raincheck.

I replied "Sure," but honestly, I wasn't planning on contacting her again. She'd already blown me off twice, and wasting my afternoon wasn't really helping her case.

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26. We’re All Confused

On the third date, we hit a club. As it got late, we booked a Lyft to skip the rush. But as we were leaving, a guy yanked my arm. He accused me of ditching him with the bill at a club, but he had me mixed up with someone else. Despite explaining this, he got angrier, tugging at my arms.

My date tried to shield me by pushing the stranger away, but that just ticked him off more. Security thought we were starting trouble, while we were trying to explain things. In a blink, the dude lunged at me.

Luckily I had my taser. I zapped him and down he went. I'm positive he had got the wrong person, but boy was it scary.

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27. Third Wheel

I'd been chatting with a gal for a bit. She was hot and cold, mostly cold. I was ready to step back, but one lonely Saturday she invited me for drinks. I thought, why not?

Meeting her at the bar, I found her and her friend, a chatty 20-something. It was clear my date was more focused on her friend than me. Her friend's husband was apparently an odd, jealous dude. I went with the flow, had some drinks, while the friend poured her heart out. I felt like an outsider, but at least I wasn't stuck at home.

Then, an hour or so later, plot twist: The husband shows up.

He storms up to our table, snaps a pic of all of us, and whispers a chilling threat at his wife before walking out. His wife freaks out and decides to bail. My date walks her out, and we step outside for the goodbyes.

Finally, I thought, a little one-on-one time.

I turn around and my date has already gone to her car. She drives off without a wave or anything. Suddenly, I'm flying solo. I returned to the bar for more drinks, but I'm awful at meeting people in bars. An hour later, I headed home.

28. Too Much, Too Soon

Met a cool guy online around two decades ago. He was smart and hilarious, so we swapped numbers. Talking to him was great. We're both 5'7", or so he said. I was early 20s, he mentioned being early 30s. Planned to catch up at the local mega flea market on a Saturday.

When we met, he was, tops, 5'4" and looked over 40; I felt tricked. Yet, I had a thing for him, so rolled onto the date. This was the first time we'd actually met, and he was on me like white on rice, kissing, hugging, clinging—I struggled to move. Too much.

Post-market, he suggested we head to his hotel room. I declined, to his chagrin, but thankfully, he wasn't violent or nasty. At that point, I was ready to blow this popsicle stand. Eventually, he took the hint.

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29. Entertain Me

I arrived for a coffee meet-up and within a snap, I knew this wouldn't work out. But hey, I thought, let's just be nice. After fifteen minutes of trying to have a conversation and getting one-liners in return, I paused. I mentioned that being chatty came with my job, but I was finding it hard to maintain a conversation with her. I then asked if everything was alright.

I was genuinely concerned for her since her behavior was so unusual, and besides, I'm usually a chilled out and fun date. Her response was so upsetting: "Oh it's just funny watching you struggle". I looked at her in silence for a few moments, before I flatly declared that she's not a nice person and left. That one still leaves me shaking my head.

Worst Dates factsShutterstock

30. A Journey

I matched with this cute girl on Tinder. Things clicked and we arranged for drinks. On the day, she was running late but asked me to meet her halfway since it was getting late. It was all a little odd, with her texting directions, but I went with it.

I ended up at a house where a woman who was definitely not my Tinder match answered the door. I realized I'd been catfished but decided to be polite anyway. Inside, she had a big fight with her mom, then took me to her room.

That's when I found out her crazy secret: The was a huge hoarder. Her room looked like a dumpster and there was even a half-eaten kebab on her bed. Despite the mess, she wanted to stay in instead of heading for drinks.

She started making advances as the night wore on, but I turned her down. I made an excuse about needing the loo, but I really just bailed out and went home.

Then I got a storm of nasty texts from her, even threatening to come to my place with her friends. The scariest bit was when she sent me my own address, which I never gave her. Luckily, she didn't show.

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31. On Thin Ice

So I was supposed to have a chill coffee date, but our mall set up this ice rink she was dying to try. I'm not exactly nimble on ice, but I figured putting on a goofy performance would get her giggling. Boy, was I wrong. In no time, I slipped, messing up my ankle and wrist big time.

I needed help to stagger off and chill on a bench, hoping for a quick recovery. But here's the punchline—she couldn't give a damn and just went on skating solo, catching another skater's eye. Next thing I know, they jet out of there, and she doesn't even glance back to see how I'm doing.

Worst Dates factsShutterstock

32. Dinner And A Show

There was this girl in my tech support class who seemed to know zilch about computers. I'm talking so clueless, I thought she'd got lost and just decided to hang. Maybe big businesses weren't her groove, but either way, I didn't think she'd hang around, so I took a shot and asked her out.

Turns out, she was an actress wannabe, not a tech geek. She was just testing whether she could portray one. The date was mostly okay until the food showed up, and then things went south. She started making a playground out of her plate and added sound effects. I made a joke, "Hey, no playing with your food."

She shot me a dirty look and went back to her food games. At this point, I threw my hands up. Yeah, she was a hottie, which probably made me look past all the quirks...until she started serenading to her steak. That was my cue to bail.

Worst Dates factsShutterstock

33. Fate Can Be Funny

So, I finally caved and went on a date with this coworker who'd been asking me out forever. As predicted, it was a total disaster. The dude would sit there, ogling my chest, then out of nowhere, he'd drop some random trivia before his eyes returned to my boobs. It was so bad, I decided to bail – literally. I tried to escape through the bathroom window. But that's when disaster struck – I got stuck. Yep, trapped in the window so tight the restaurant had to call the fire department to pull me out.

My date, the gentleman he was, wandered in to watch. But instead of helping, he was eyeballing my butt, even trying to grope it. The firefighters immediately kicked him out. Not to be deterred, he found me at the back of the pub, where my upper half was sticking out, and tried to pucker up. Luckily, I got a good swing at his face.

The firefighters sent him packing. Next day at work, he sported a giant shiner and was telling people I freaked and hit him. Fast forward three years, I met my future husband. On one of our date nights with friends, my hubby, who's a firefighter, casually shares this hilarious story about rescuing a woman jammed in a bathroom window trying to dodge a date!

Embarrassing kidsPexels

34. Ah, Young Love

In eighth grade, I finally got the courage to ask a girl out. She was a friend of my best friend's girlfriend, so we figured, hey, let's double date! At the movies, things were going well. I was next to her and my buddy was with his girlfriend when a couple of her pals walked in.

They spotted her straight away. She called them over and when they came, she asked me to move so she could sit with her pals. I agreed and then just left the cinema.

Creepy DatesShutterstock

35. No One Had Fun That Day

This girl seemed perfectly normal and was really sweet. Things immediately went south due to the circumstances. We thought it'd be cool to meet at this busy bar with a huge patio on a weekend afternoon. The place was crammed, and we got squeezed into a tiny table meant for two. Just as we were settling in, an older lady called out my date's name in surprise.

Turns out, it was my date's mom! She was there hanging out with her friends. So, we ended up spending our first date with her mom practically sitting in our laps, making small talk and nursing our drinks.

Worst First Date FactsShutterstock

36. Red Hot Love

So, I asked this girl I really liked to a movie and she said yes. We yakked about random stuff before the show and suddenly, she's talking about her boyfriend. It hit me hard, but I acted cool. About halfway in, I bailed to the loo and decided I was done with her.

Strangely, she rings me a week later saying the boyfriend bit was a lie 'cause she was jittery. I was into her, so I thought, "why not give her another shot?" The second date wasn't any better though. She says she's a volunteer firefighter, which I thought was rad. But the only thing she gave a damn about was... fire. "Seen a house on fire? It's pure art!"

Fire, fire, and more fire the entire night. No matter how hard I tried to change the subject, she always swung it back to flames. No need to tell you, I never gave her a ring after that!

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37. Did It Hurt When You Fell… From Bed?

We were messing around and suddenly, I flew out of the bed and landed on my head. I kept passing out so he rushed me to the hospital. There I was, sat with a neck brace, waiting for tests, when he asked to see me again. I just gawked at him. After twelve hours, they let me go with a serious concussion and the doctor told me to take a month off from work.

I couldn’t afford to do that, so we negotiated it down to a week, given I promised to sleep most of the time. For a week, I was drugged up, sleeping. I'd wake up just to eat, have a drink, use the bathroom and take more meds. Honestly, the intimate part wasn’t even worth it… and no, there were no encore dates with him.

Doctors Knew Lying FactsShutterstock

38. An Unsettling Turn Of Events

I met this really attractive and smart chick online who was just a bit older than me by like five years. She was a dentist and we had a blast on our first date. We ended up at my place — she left some scratch marks on my back, but the night was cool. I woke up to the noise of breaking dishes. When I checked it out, she was chucking all my plates in the trash!

As chilled as I could, I asked why was she doing this. She weirdly told me I needed better plates. Huh, fair enough. Then she wanted to go back upstairs and snuggle. That's when things turned freaky. She started murmuring about losing her dentist license and how she wasn't what she seemed. I sorta chuckled, but I was getting uncomfortable. Then she ran to my bathroom and locked herself in.

At this point, I was legit scared she might do something crazy with my razor. I hear stuff being emptied and freaked a bit, asking her what was up. She came back saying she messed up. She was supposedly married, had a kid but couldn't see them or stay at home. This made me realize she was having some serious issues.

I invited her downstairs and said I'd make some eggs. She broke all my plates, remember? So I suggested a quick sandwich from a nearby place. We got there, didn't talk at all. I grabbed two sandwiches and we ate 'em on an outdoor bench. She thanks me, calls me cute, and then just bails. Nothing more from her, then or ever.

Creepy momentsPexels

39. The Art Of Pitching Woo

When I was 10, I had a big crush on my best guy friend. Although he probably still found girls gross, I was a born romantic and dreamed of a perfect date. So, we ended up at Olive Garden for dinner, my mom chaperoning us. I snuck off to the restroom and changed into my single fancy dress.

Next, we hit the movies. I made sure my mom and sister sat away from us. Playing the scared girl, I asked him to hold my hand if it got too scary. The cherry on top? As we dropped him home, I pecked him on the cheek to his shock, right in front of his mom and sister.

For years after, I was the butt of all jokes, his sister never missing a chance to tell this story to our friends. Talk about embarrassing! I likely left him scarred through his early teens, but hey, who can blame a 10-year-old romantic?

Cringe momentsShutterstock

40. Jokes On Him

I met up with this guy at a bar who didn't really match his photos. My first thought was, maybe he's got a great personality. But as the date unfolded, I realized that wasn't the case either. He started grilling me about my hobbies, then making fun of them. What sticks out was when I said I liked comedies and he answered, "I prefer documentaries because they're educational. I rely on my friends for humour." After enough of that, I dipped. But get this, he still texted me later and asked to hang out again. Funny guy, huh?

Most Embarrassing Childhood Memories factsShutterstock

41. A Whirlwind Romance

I met up with this girl at a bar. She kinda insulted me right away by saying my hair was gross - I mean, I keep it clean, she just doesn't dig long-haired guys. I let it slide and we went on with our chat. But then, she started boasting about her history with taller men (I'm 5'8" for the record) and asked me to spot her $30 for her manicure.

That wasn't even the most awkward part. She poked fun at me living at home, even though she also stays with her folks. When our get-together was winding down, she asked me to chill in her car. Things veered into politics, not my cup of tea, but at least we moved on from her exploits. Finally, she decided to cut out 'cause some other fella was there to pick her up. I was left feeling pretty baffled.

Treat yourselfUnsplash

42. Three’s A Crowd

Once me and my buddies went to this movie festival, way out in the sticks. The only way to get there was by boat. Folks could either camp out or shell out for a swanky hotel. I was a student, so camping was the way. They even had an outdoor bar and restaurant.

My then-girlfriend and I were sharing a tent. One of my exes was there too. We were cool and she hung out with us. Fast forward to the first evening and we were grabbing grub. Guess who I bump into? Another ex. I was polite, said hi and all that.

Next thing I know, she's at our table. It's starting to get kinda uncomfortable. Then, boom! Another ex shows up and tags along, current boyfriend in tow. Just picture it - my girlfriend, three exes and a bunch of others at the same table.

To top it all off, one cheeky buddy goes and points out the whole situation super loud, so everyone knows what's going on. Needless to say, I ended up with another ex by the time the night was done.

Fake friendsShutterstock

43. Mistake Number One

So, I had a chat with this dude on OkCupid for a few days. Realized I goofed by telling him where I worked. Outta the blue, after a casino night with his buddies, he's hit luck and decided to buy me a gift. He seemed pretty hopeful about our interaction.

I felt uneasy - we barely knew each other, right? Told him as much, but the guy won’t take no for an answer. Said he was jumping on the next bus to drop the gift by my work. Said to meet him there if I was interested and had the same vibes. Ignored him.

And yeah, didn't go to meet him. After work, saw him loitering at the bus stop, brown bag in hand. Yup, blocked him soon after and found a new job. The previous one was just a part-time gig I was doing during college, so finding a new one was a piece of cake. I didn't feel secure there anymore.

Worst Blind Date FactsShutterstock

44. Memory Of A Goldfish

I was chatting with this girl on Tinder for a bit. Some nights we would even have phone convos and she was super chill. We planned a date to go to the city's food market and I offered to pick her up. I pinged her when I was enroute and again when I got to her place. But I got no answer.

She lived in this gated apartment so all I really could do was call and text. I think I must've been waiting for around 20 min trying to let her know I was there, but no luck. I snagged a burrito at a joint near her place and then she finally calls and tells me — get this — she "forgot our date"… and that was after I'd, like, confirmed it just half an hour prior.

Then she begged me to swing back and pick her up, and, like an idiot, I did. When we finally started our date, most food joints were closed and she didn’t want to hit up a bar or anything. She barely put in any effort for a chat and was just on her phone while I was driving. Eventually, we just decided to call it a night.

Haunting Embarrassing Moments factsShutterstock

45. A Sly Twist Of Fate

This was the first chick I dated after leaving the military. She faked an ankle twist when the bill arrived, making me lug her to her car like a firefighter. She tried to bait me into inviting her over, saying she couldn't drive 'cause it hurt her foot.

When I asked if she had any family who could get her, she shot it down. I was by her car door, and she asked me to check if her foot looked alright. Gullible me, I leaned in, and she tried for a surprise smooch. I backed off, saying I wasn't feeling that spark.

She labeled me a jerk, then shot out of the parking lot. Later, she flooded my phone with messages, apologizing and claiming we were made for each other.

Lost Crush FactsShutterstock

46. He Tried So Hard And Yet…

So, there was this girl I was totally into and managed to persuade her to join me for a date. She mentioned she'd never been to the local pier, and knowing we lived near the beach, it seemed like the perfect opportunity. Feeling excited, I drove her to the beach, and we began walking along the pier together.

She wasn't too thrilled from the get-go. We halted before reaching the edge, me leaning on the railing looking down at the water, while she stood further back. It was clear she wasn't enjoying it. I tried to lighten the mood, pointing out the amazing view. To our surprise, two pigeons chose that moment to join us, which I found comical.

But then, the birds started getting frisky right there in front of us. I scanned around, trying to distract from the bird exhibition. Spotted a lovey-dovey couple on the pier with roses. Thinking we could learn a thing or two about romance, we made our way over.

Once we got there, something felt odd about the couple. Soon we realized, they were in tears. And then, they tossed their roses into the sea. We had unintentionally crashed a sea burial.

It was clear this was one of the worst dates ever. As the reality of my failure began to set in, I noticed my date was acting strangely. Reading her body language, it finally clicked. She wasn't telling me about the pier to suggest the date, she was actually scared of it. Turns out, she was scared of both heights and the ocean.

Chris Hemsworth factsFlickr, Kevin Gibbons

47. It Could Have Gone Better

I got chatting with this girl online who was really cool and relatable. We had loads in common, like our interests and political views, and I figured we could really gel. We decided to meet face-to-face at a coffee shop. Keep in mind, I ain't exactly Brad Pitt and up till now, she hadn't seen a single photo of me.

We had set up a way to recognize each other. She walked in and I knew her right away from her outfit, so I started to wave. She looked kinda confused, came over and said, "Sam?" I said yes, and all she said back was, "Haha...NO".

Parents Never Admit FactsFlickr

48. A Relaxing Vacation

I bumped into this guy, and we just clicked. Like instantly. I was over the moon, thinking "At last, a real man". One day, he suggested: "I know this nice house we could stay at this weekend". I was game—until we get there and he whips out a crowbar. He’d "forgotten his key", he said.

That gave me the creeps. I asked whose place it was, and he said it's his dad's vacation joint. He's cool with us being there. I swallowed my instinct to bail, thinking maybe I was being paranoid. We hung out for like four days, no drama.

I crashed in the main bedroom, cooked up a storm in the kitchen, you name it. As we're rolling out, he's like, "Check out what I scored", waving about some bling and credit cards from the house. Panic mode kicked into overdrive. I thought he was just acting out, still assuming it was his dad’s place.

Then, the truth dropped. Turns out, we’d just raided a house. And it wasn’t his dad's place, but his mom's ex-boyfriend’s. They definitely hadn't green-lit this little getaway. His stepdad had even got a restraining order against him after a similar past episode.

Fast forward a couple of weeks, and I’m getting pulled over and dragged out of my car because apparently, I'm now implicated in this mess. Thanks to the victims, who were rightfully upset about the whole thing. Somehow, I narrowly escaped getting locked up over this mess.

Creepy Moments FactsShutterstock

49. Cats, Cats, Everywhere There’s Cats

I connected with this girl online. We were both kinda nerdy, into the same pop culture stuff, and her pictures were cute. We played phone tag for a hot minute before finally setting up a date. She invited me over to her place for dinner and a movie. Felt right, as we both liked chilling at home.

She claimed she was from Houston, but her place was actually an hour plus outta the city. When I pulled up, my jaw just hit the floor. She was staying in a trailer surrounded by woods and mounds of garbage. No trash service it looked like, everything was just tossed outside. Thought I was seeing cats everywhere, but damn if there weren't giant rats mixed up in there.

Even though I was kinda freaked out, I’d driven all this way, so I got out and knocked on her door. I nearly retched when I got hit with this wave of cat pee stench. Inside, it was a crazy cat lady scene. Old cats, young cats, all colors, just everywhere.

Her mom was supposed to 'cook' for us. It was just a microwaved dinner. Then, the girl practically mauled me once we got to her room. I figured I'd escape to the restroom, only to find it was flooded with cat waste and litter. Boxes of it, even in the shower. Yeah, I wasn't sticking around. I made some lame excuse about forgetting flowers in the car and I bolted.

Crazy Wills FactsShutterstock

50. Oh, Those Summer Nights

A couple years back, I scored a date with this girl from my college math class. She caught my eye, but, man, I was way too chicken to ask her out. Then, one summer day, she hit me up on Snapchat, asking about tea spots. I recommended a few and asked her if she fancied visiting one with me.

Bingo! She agreed. I remember picking her up and heading to the tea joint. We had an awesome time, even played a game of Jenga. Not wanting the fun to end, I took her to a nearby lighthouse. It was one heck of a night, just getting to know each other and laughing non-stop. Unfortunately, night fell and it was time to say goodbye. But we made plans to hang out again.

Fast forward a week or two, waking up to my feed on Instagram to see the first post - her cozying up to some guy at the same beach. I thought she was single, not seeing anyone. Man, it was a shock. Felt like a punch to the gut even though we'd just hung out once.

Strangest things done online factsShutterstock

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