Dating Horror Stories

November 25, 2021 | Samantha Henman

Dating Horror Stories

Dating can be exciting, heart-racing, and incredibly fun. However, to say the very least, going out with a stranger is risky. As these Redditors know all too well, sometimes the search for "happily ever after" can transform into a downright dating horror story.

1. Twist Ending

I once went on a blind date with this girl. We started with a movie, and everything went okay throughout. The real disaster actually only happened as we left the theater.

After the movie finished, as we were pulling out of the parking lot, she saw her father leaving the same movie…with a woman who definitely wasn't her mother.

Blind datesUnsplash

2. Stay Hydrated

It was my freshman year of college. He took me to Wendy's for a date because neither of us had a lot of money. He had one of those monotone voices, and could drone on and on and on about nothing. He was telling one such story when I swallowed my water the wrong way and started coughing.

This was still a date, so at first, I tried to politely expel the water, but to no avail. As he continued to talk, I started hacking all over the table. Tears were streaming down my face, water was dribbling down my chin, and I was pounding my own back at a futile attempt to get the devil water out of my system.

He kept talking. Trying to hold the water in at first was a bad idea. I could not stop coughing. But then it got so much worse. I bent down under the table, hoping the angle would make it easier to cough up the liquid. Everybody in the whole restaurant was staring at me in silence. Except for my date, of course.

He was still telling his story. I finally finished hacking up my lungs and tried to listen to the rest of his story. I had no idea what he was talking about. He continued with his anecdote, unfazed by my wet, red face and smeared makeup.

When he finally finished, I apologized for my coughing fit and explained that I had swallowed my water the wrong way. To which he replied, "Oh, I was wondering what was wrong with you". Thanks, my dude. We did not have a second date.

Blind datesPexels

2. He Tried So Hard And Yet…

I convinced a girl who I was crazy about to go out on a date with me. I knew I had to make it count. We lived by the ocean and she had dropped the hint that she had never been out on the pier at our local beach. Challenge accepted. I nervously drove her down to the beach and we proceeded to slowly walk out on the pier together.

She seemed hesitant from the beginning. We stopped short of the end and I leaned against the railing over the water while she stood back a bit from the edge. She didn’t really seem into it at all. Awkwardly I said, “This is a great view, huh?”

Just then, two pigeons flew up and landed at our feet. “Sweet, chicks dig birds,” I thought to myself. Then it went SO wrong. To my horror, the birds began to make passionate pigeon love in front of us while neither of us spoke. I had never witnessed such athletic passion.

I quickly scanned around and saw a couple holding roses on the other side of the pier. “Awesome, they look romantic, chicks dig romance,” I thought to myself. We quickly walked away and stood next to the happy couple.

The man and woman were holding each other and both holding roses, but something seemed off. I glanced up and noticed that both were sobbing, the girl I was with noticed too. As we were both looking, the couple took their roses and cast them into the sea. I had posted us up next to a funeral, some kind of sea burial.

Between animal shenanigans and funerary rites, I had executed one of the worst dates of all time. Just as I had accepted my failure, my date started getting fidgety. Based on her body language and her expression it dawned that she hadn't told me about the pier as a hint but because she was terrified of it. Turns out she had a fear of heights and the ocean.

Chris Hemsworth factsFlickr, Kevin Gibbons

3. It Could Have Gone Better

I met this girl on the Internet and she seemed really nice and down-to-earth. We had a lot in common including our hobbies and politics and stuff like that, so I thought we might hit it off. We agreed to meet up in person at a coffee place. Now, bear in mind that I'm not super attractive and up to this point, she hadn't seen any pictures of me.

Instead, we had pre-arranged recognition signals. She walked in the door and I spotted her by her clothing instantly, so started waving. She got this sort of uncertain look on her face, then walked over and said, "Sam?" and when I say yes, her response destroyed me.

She just said, "Haha...NO".

Parents Never Admit FactsFlickr

4. Cats, Cats, Everywhere There’s Cats

I met this girl online. She seemed nice, geeky, and into a lot of the same nerd stuff that I was. She was cute in her photos too. She dodged me several times about going on an actual date, but finally, we managed to set something up.

She wanted me to come to her house so she could make us dinner and watch a movie together. We were both introverts, so that was fine by me. She said she lived in Houston, but it was actually over an hour outside of it. When I got to her 'house', my jaw dropped.

It was actually a trailer in the middle of the woods on a wooded lot full of trash. Turns out, they didn't have trash service, so she basically just threw it outside. At first, I thought I was seeing cats everywhere, but it turned out to be cats mixed in with a few massive rats.

Still, I'd driven an hour plus, and I was already there, so I climbed up the decrepit deck and knocked on the door. When she opened it, the smell of cat urine poured out of the trailer and invaded my nostrils. When I got inside, there were more cats everywhere. Orange cats, brown cats, old cats, young cats. Cats everywhere.

Her mom was "cooking dinner" for us, which was frozen microwaved dinner. This girl then dragged me to her room and lunged at me like an animal in heat. I told her I had to go to the restroom but it was covered in cat waste and litter. Just box after box, in the shower and everything. I couldn't do it.

I went and told her I’d forgotten flowers in my car and drove away as fast as I could.

Crazy Wills FactsShutterstock

3. True Blind Date

I once had my blind date walk into the restaurant wearing a niqab. She was not Muslim—and her reason for wearing one made me want to flee. See, she wanted us to have a conversation without me knowing what she looked like. Kind of a “what the heck” moment out of a TV show…but I saw her point.

I ended up disliking her based on her personality.

Blind datesPexels

4. For Your Eyes Only

I went on a date with this guy who seemed really sweet. We went out to a really classy dinner. The food was great, the atmosphere was fantastic...but at the end of the main course, he whipped out his phone and started showing me pictures he'd taken of his private area. Like...different angles, lighting, and dynamic effects.

I rode with him to the restaurant, so I had to sit next to him on the ride home and fight the urge to fling the door open and tuck 'n roll.

Blind datesPexels


5. The Talking Cure

I had recently started dating this guy, and we were on our way to Circuit City to browse around for a few things he needed for his computer. While in the car on the way there, an annoying techno song came on and I commented on how I couldn't stand how often they played it on the radio.

He turned it up a bit, telling me that he liked the song. I laughed and jokingly said, "OK, well I'm not talking to you until this song finishes!" I smiled at him and looked away, just enjoying the car ride. This turned out to be a huge mistake. We park the car and I immediately sense that something is wrong.

He's walking a few paces in front of me, clearly trying to avoid walking side-by-side. I let it go and run to catch up to him. I take his arm and kiss him on the cheek and proceed to walk to the store with him. Again, he seems distant. I ask him what's wrong and he tells me he's fine.

I let it go and decide to enjoy the shopping we were there to do. We're browsing through the store, and suddenly I realize that he's nowhere to be seen. It's around 7:00 PM at the time and the store was pretty crowded. I figure he must have wandered to another aisle and I do the same.

15 minutes later, there is still no sight of him. AT ALL. I'm walking through the store searching for him, and nothing. It's now 8 PM. I call his cell phone and it rings out. I walk out to the car, and it’s empty. There are about six other stores in the complex and I wasn't about to walk to each one searching for him.

It's now 8:45 and I'm getting scared. The store closes at 9, so there aren't that many people there. Finally, the store is closing and I walk out to the nearly empty parking lot. Well, there he is, sitting in the car. I run over with tears in my eyes, asking what happened.

He looks at me calmly and says, "Now you know how it feels when the lines of communication have been cut".

Blind datesUnsplash

5. Don’t Dare Compare

After my freshman year of college, I met a guy on OK Cupid and we went to get dinner. He offered to give me a ride, but I said no. He was a couple of years older than me, so I felt unsure. At dinner, he started talking about how he'd started his own business after college and how it was going well. Good for him!

He bragged a bit, but hey, that's an accomplishment. After we ordered food, he said to me, in the creepiest voice ever: "Let's play a game". He wanted us to take out our wallets and compare what was in them". It wasn't a joke. He literally started showing me his credit cards and bragging about the high limits.

He ended with, "Clearly you can't afford to pay for this dinner, but don't worry, I can cover you". I was mad and protested, but he wouldn't take no for an answer. As we left, he said he wanted to show me his car. Unfortunately, it was nearer to the restaurant entrance than mine was, so I had to walk by it.

It was a white, windowless van. He begged me to get in the back with him, right there in the parking lot. I was pretty glad I drove separately.

Customers paying waiter at restaurant.Getty Images

6. Eat Fresh

I went on a date with a guy that I met online. He told me to dress nicely as he was going to take me out for dinner. He took me to Subway and ordered a foot-long teriyaki chicken sub. He then looked at me and said, "I hope you like teriyaki chicken". We shared the sub in his car. Safe to say there was no second date.

Co-Worker KarensShutterstock

7. Nay To PDA

I went to meet a woman in her 30s at a Starbucks. I showed up to see a woman pushing 50, maybe more, and she was much larger than she initially claimed to be.

She immediately started to talk about getting intimate with me, asking me what positions were my favorite and stuff like that. This was in the middle of a crowded Starbucks where there were children around.

She then reached across the table and tried to grab my hand and touch me, to which I told her that PDA makes me uncomfortable. This was a lie, but I didn't want to cause a scene or hurt her feelings. 

I told her that I wasn't feeling too well and that I should probably go. I thought that would be the end of it, but my nightmare was just beginning.

She followed me out, grabbed my posterior, tried to push herself against me, and tried to kiss me. I told her again that I was not comfortable with PDA, and after several repeats of this, she finally let me get into my car. I got out of there as fast as I could and took some time away from the dating scene after that encounter.

Weirdest Date FactsShutterstock

8. Patiently Waiting

Over 25 years ago a coworker set me up on a blind date. The evening arrived, and I was a little early at the restaurant. Feeling anxious, I ordered a drink, and chatted with the waitress, telling her I was on a blind date. After the first drink, I checked the time and my date was 15 minutes late. City traffic. I figured. But the seed of doubt was planted.

I finished the second drink quickly while battling new anxiety mixed with doubt, and a bit of fear. I took a deep breath, sighed, and tried to relax. "Still waiting?" the waitress asked, startling me out of my worry. I tried to laugh, but it felt hollow. Checking the time again, my date is now 45 minutes late. I felt terrible—but I didn't know this chilling truth.

My face was red and I wanted to shrink into the booth. At the hour mark I couldn't take it anymore and gave up. As I was paying, my waitress found me. "She stood you up," and I just nodded. Then I walked out the door and went home. I found out two days later, my date had passed in an auto accident on the way to the restaurant.

Embarrassing datesPexels

9. The Last Laugh

Went on a date with this girl a couple of years ago to a comedy show. I picked her up and she was a little tipsy from day drinking with her friends. We go to the comedy show and get seated in the first row. I don’t recall who the comedian was but he did a lot of crowd work.

Halfway through, I look over at my date, and she is head back, mouth open passed out. I knew what was coming—but it was still brutal. The comedian begins ripping into me about boring my date to sleep for five minutes. By this point, my date wakes up and is with it for a minute or two, but then falls asleep again!

By this point I could tell the comedian would not let me live this down and everyone around me was laughing and giving her concerned looks. The waitress comes over and pulls my date to the side, giving me an excuse to get my date away from me (good on her for looking out), and asks her if she was safe.

Thankfully we were new in our short relationship because she told me after that if we were closer she would have pranked me or something. Didn’t follow up on another date.

Embarrassing datesPexels

7. Paging Dr Freud

I went out with a guy who talked about his mother literally the entire time. I knew her favorite foods, movies, where she went to college, how she makes her spaghetti sauce…you name it, I heard it. At one point I suggested he date his mom since no other person could compare to her. He looks at me almost like he's contemplating it.

I look at him like he's psychotic, and he yells at me and says that anyone who is half the woman his mother is should get down on their knees and thank God for their blessing. Fast forward two years and he married his dad’s high school sweetheart. True story.

Worst Blind Date FactsShutterstock

9. Fossil-Like Opinions

I once went on a date with a girl and this is how the conversation went.

Her: "So, what’s your favorite book?"

Me: "Tough, but when I was little I LOVED Jurassic Park".

Her: "Yuck, Jurassic Park".

Me: "The book or the movie? EVERYBODY loves Jurassic PARK!"

Her: "I don't believe in dinosaurs".

Me: "Fossils?!??!??!"

I was already at the end of my rope, but her next response just blew my mind.

Her: "I don't want to get into it, but I think fossils are BS".

I ended the conversation there and held onto the night, that is, until later on when she told me, "I don't believe in outer space," and my head freaking exploded.

Couples Broke Up FactsPixabay


10. The City Of Dates

I had just moved to San Francisco from college and started talking to this guy on Tinder who was in his late 30s/early 40s. I hadn’t had much luck with older dates previously but I decided to be more open-minded. We got cocktails and on the date, I acted as pleasant and engaged as I could even though there was not much chemistry.

After one drink we decided to part ways, and he offered me a ride home. Once I got home, I received a message that was paragraphs long from him! He really wanted to leave the whole time but stayed to pay for my drink and give me a ride home. He also let me know I was overweight, unattractive and I had acne that was disgusting.

My heart sank after this unprompted and completely unnecessary message. I immediately deleted it and blocked him but the words still replayed in my head. Even now I still think about it, and it makes me sad that I dimmed my light because some guy decided to be awful.

Embarrassing datePexels

11. Change Of Plans

I went on a date after talking with someone for a couple of weeks. The conversation online was pleasant and involved the usual small talk about hobbies, interests, etc., There were no red flags, or so I thought...We arranged to meet in the city for a coffee. When I arrived and she was already there...and she looked nothing like her pictures.

I thought to myself, "Oh, well most people tend to embellish their photos. Let's see what she's like in person". That's when I messed up BIG time. We got to talking and at one point, she asked me what I'd be doing the following weekend. I love camping and exploring, so I just told her I had a camping trip with my mates.

She asked me if she could come along and I replied, "Um, no...We only just met". She then proceeded to lose her cool, throwing a tantrum as if we'd.been dating for years. "How dare you not take me along," she snapped at me. Yet, even after she caused a scene, my idiot self decided to see the date through to the end. She continued to ask me more questions about the trip, asking which campsite I'd be going to.

I gave her a rough estimate of the location and she replied, "Oh, that's nice. I'll see you there..." I thought that was a weird response and reiterated that I was not comfortable with that. She replied, "No. I'm going there no matter what you say. You won't see me coming". She then let out a maniacal laugh.

That was the last straw for me. I stood up, placed my money on the table to pay for my coffee, and walked away.

Dealbreaker DatesShutterstock

12. Three’s Company

I met a girl on Craigslist. After a few messages, we set up a date at a bar downtown. I showed up and there was an unexpected surprise waiting for me at our table—she was already there with a guy friend. No biggie; I just assumed she was playing it safe. They were at a two-person table and the place was packed.

They already had drinks, so I grabbed one for myself and put it on my tab. My date and her friend proceeded to ignore me. I tried to join in on their conversation a few times but neither of them acknowledged me. Even when I directly spoke to them to get their attention, I got one-word answers with attitude.

So, I finished my drink, paid my bill, and left without saying a word. Later, I get a barrage of messages from her calling me mean and awful for sticking them with their own tab.

Nightmare FamiliesShutterstock

13. Small Town Woes

I was on a dating app in a smallish town and I had already gone on a few boring dates. But eventually, I matched with this one girl who agreed to meet with me. I was thrilled, but there was something very odd about her and the conversation we had.

She was eager to meet; almost too eager. I got to the Starbucks and waited inside for about twenty minutes past our agreed meet time. The girl texted me to tell me she was running late, and she asked me to stand outside so she could see me as she drove by.

I looked over and there was another dude standing on the sidewalk with his phone in his hand. I recognized him from the gym, so I asked him if he was also meeting a girl. It turned out the girl was pulling a fast one on us both as revenge for her girlfriend who we both apparently dated.

Dealbreaker DatesShutterstock

14. The Sound Of Silence

On our date, we went to Dave and Buster's. I could tell she was uncomfortable. I tried to bring up topics for us to talk about, but I was only getting one-word answers or literally, “I don’t know,” even when I asked her questions about herself. We sat in silence for about five minutes before she finally showed signs of life.

She got up to go to the bathroom and when she came back, I just straight up said to her, “Hey, if you’re not having a good time, you’re more than welcome to leave. It’s perfectly fine". That's when things went completely south. She got insulted by what I said and picked up her purse to leave.

I repeated myself and said, “If you’re having fun, I’m more than happy to stay, but like, we’re not even talking right now". So she got up and left and I ordered another drink, waited a bit to watch the rest of the game on TV, then left. I got a text from her saying how insulted she was that I would ask her if she wanted to leave, etc.

I just said, “I tried talking to you for 15 minutes and got no responses". She then explained that sometimes she just doesn’t feel like talking and I was cruel for not being okay with that.

Worst Blind Date FactsShutterstock

15. Bathroom Break

I'd been totally infatuated with my co-worker for months, so when she finally agreed to let me take her out, I was ecstatic. Little did I know that it would only take 30 seconds for me to lose all interest in her. At some point during our date, we walked down a back alley by the bar and she said she needed to go #1—but what she actually ended up doing shook me to my core.

She pulled her jeans down, TOOK A #2 behind a bin, then searched through the bin for a sheet of newspaper to wipe herself with. I stopped talking to her immediately after that.

Scariest ExperiencesShutterstock

16. Not In The Stars

Our first date was at a Japanese restaurant. She asked me for my star sign and I replied, "Scorpio". She then leaned over the table and she totally caught me off-guard with her next move—she slapped me clean and hard, right across the face. Naturally, I was shocked and confused. I mouthed "What...?" and she firmly said, "I NEVER date Scorpios".

I went to the bathroom to compose myself, and when I came back, she had gone and paid for everything.

Dealbreaker DatesShutterstock

17. Toe Thanks

I went to meet a guy for the first time at his house. I liked him a lot, but when I got to his place, I was immediately turned off by what I saw. There was a pile of toenail clippings on his coffee table. And it wasn’t one recent clipping. It was like, many clippings. I went straight back out the door.

Awkward DatesShutterstock

18. Not A Gentleman

This guy and I were eating dinner after chatting for a couple of weeks. Out of nowhere, he said something completely unrelated to what we were discussing, and it had me fuming. “So, you order for this to work, you’re going to have to share yourself, right? My friends and I like to pass girls around".  I was dumbfounded.

After a bit of stuttering, I told him I didn’t think it was going to work. I asked for a to-go box and my portion of the check.

Awkward DatesShutterstock

19. Blinded By The Dawn

In my second year of college, I was pulling an all-nighter at the same time as one of my friends, who was very cute. We weren't in the same place, but we kept messaging over Facebook. It was really nice just talking with her. I had been single for about two months and was feeling confident. When dawn hit and our papers were done, she asked me out for celebratory breakfast.

I looked like I had just finished an all-nighter, and she looked radiant. As our breakfast went on, we talked, laughed, and the caffeine begins to mix with the satisfaction of completing my work for the semester. I’m feeling like I'm in a really good place. The sun is starting to fill the windows of the restaurant we're in, and there's this warm light everywhere.

She smiles coyly and asks me if I'm over my ex. I smile, say I am and I'm already thinking about who I'd like to ask out next. She smiles even broader and asks me who that is while touching me on the hand. And I said the stupidest thing possible. "Her name is Rebecca and she was in one of my history classes". Distinctly, this was not the girl I was out to breakfast with.

She looked devastated. At the time, I had no idea why. Realizing the mood had changed I quickly said, "I'm sad the semester's ending soon, but I'll see you in the spring!" I ran back to my dorm, ending what I would later learn was the first date with my future wife.

Embarrassing datePexels

20. Times Were Tough In The Nineties

My wife was set up on a blind date by a friend several years before I met her. They agreed to meet at a mall and then go from there. This is the late nineties, before cell phones, so he tells her he'll be wearing blue jeans and a Megadeth t-shirt and she tells him her outfit so they can identify each other. She arrives at the mall and sits down to wait.

After thirty minutes there’s still no sign of him. She’s about to leave when a guy approaches her and asks if she's waiting for a date. It's him, but wearing a completely different outfit. Confused, she asks why he told her he'd be wearing something else. His response was absolutely insane. He just shrugged and says his mom didn’t do the laundry yet. Two strikes...

They still decide to grab some food. He tried to use an expired coupon and started an argument with the girl behind the counter. At the table, he asks my wife if she knows how to cook. What meals does she know how to cook? Can she make this or how does she make that etc. The conversation continues but now he adds, "Do you do it without clothes on?" after everything.

For example, she likes to go rock climbing, “but do you do it unclothed?" Or, I like to grow my own vegetables, "but do you do it in your birthday suit?" Needless to say, my wife decided to end the date early and leave. He asks if she can lend him bus fare since his mom won't be coming to get him for several hours. He was twenty-seven years old.


Embarrassing datesUnsplash

21. A Quick End

I sat down and he immediately said, "Oh yes, you are hotter than your pictures and you're my girlfriend now". Cleary, he came on real strong. I chalked it up to keenness at first or maybe a weird sense of humor. I figured I'd at least stick around for a drink or two, just to feel it out. I even offered to buy the first round, partly as an excuse to get away from the table for a second.

I made some unrelated comment to the bartender that made him laugh, and when I got back to the table, my date caught me completely off guard. He started yelling and slamming his fists on the table, demanding that I tell him what I said to the bartender and whether I thought he was good-looking or not. He had somehow gotten jealous of this bartender five minutes after meeting me.

Hotel HorrorsShutterstock

22. Miscommunication?

I had a crush on this guy in high school and my friend kept urging me to talk to him. I finally got the nerve to ask him out and apparently, he liked me too, or so I thought. We talked often and exchanged notes in the hallway. He even asked me to homecoming and I said yes. I was so excited; I bought a new dress and everything!

But when I got to the football game, everything changed for the worst. I saw my crush in the stands and I told him I was going to go sit with him for the game. He told me I couldn’t do that. I asked him why and he said it was because he was with—get this—his girlfriend. I was devastated and embarrassed, to say the least.

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

23. Why Did He Even Come Over?

I invited this guy from Tinder over to my place because he seemed pretty nice and we had a lot in common. He was decent looking on his profile, so I thought, why not? For context, I had just moved into my apartment and I didn't have a nice setup yet besides a table and a few chairs. The second he walked in, he waved the first red flag—he asked me why I didn't have any slippers for guests.

I was a bit confused but figured maybe he just lived in a fancier household than me (and yes, he made it clear he did). I said I didn't have any slippers, and he just shrugged it off. We then went to my balcony to hang out and he spent twenty minutes crying about how much he still loved and missed his ex-girlfriend. I just nodded along to be nice, but it was strange.

We eventually went back inside and he immediately started grilling me about my lack of furniture. "Where’s your TV? Couch?" When I explained that I didn't have the money at the moment to buy nice furniture, he scoffed and just kept nitpicking.

Nightmare ExesPexels

24. Maybe She’s A Werewolf

I went on a date with a girl in college, a cutie from my class who I had been trying to get a date with for a while. I picked her up to drive to dinner, and it’s worth mentioning I live in Wisconsin and it was January, so it was pretty cold outside. While I was driving, she startled me with her next move—she proceeded to undo her belt, open the door, leap out of the car into a snowbank, and run into the woods.

I had to chase her down and convince her to get back in the car with me before she lost her feet to frostbite. We didn't date anymore, but I did check in on her every once in a while.

Scariest ExperiencesShutterstock

25. Mutual Attraction

I went to pick up my blind date. She opened the door, looked at me, and said, "Ew". I'm not sure what prompted me to reply this way, but I just looked at her and said, "Yeah, I agree". I then turned on my heel and left. The entire date ran for less than five minutes.

Romantic Backfired FactsShutterstock

26. Dodged A Bullet

This happened when I met someone from an online dating app. He turned up with pupils the size of dinner plates and he was super erratic. He said he'd forgotten his wallet, so I got the first round. We were on the way to the second pub to meet his mates so they could lend him some money. During the walk there, he spoke absolute nonsense non-stop.

I was still open to giving him a chance, but then he told me a story that chilled me to the bone. He basically told me, in graphic detail, how he drowned his ex's chihuahua in a pool.  I knew I had to get out of there ASAP. Near the pub, he got a call and said he needed to answer it. At that point, we were 30 minutes into the date and already going to the next pub.

He had downed his drink in about three seconds, whilst he stood there on the phone. That's when I told him I'd meet him at the pub since it was in close proximity. Instead, I walked right past it and ran all the way home.

Creepy DatesShutterstock

27. Made For TV

I went out with a girl for a first date. She took me to a Kumdo lesson, which is a Korean sword fighting sport. I thought that was cool, but it was an advanced class and I made somewhat of a fool of myself. Still, I had a lot of fun...until I uncovered her shady ulterior motive. Turns out, she brought me there not because she wanted to go on a date, but because she wanted me to be part of a documentary about foreigners in Korea.

I was shocked, but I had no choice but to just roll with the punches since I was already deep in it. We then visited her grandmaster's house for makgeolli, and the film crew started interviewing me. They kept asking us relationship questions as if we had been going out for years. They didn't seem to understand it was the first date.

So there I was, trying to answer awkward questions without embarrassing both of us on national television.

Nightmare FamiliesShutterstock

28. The Den

He invited me into his apartment while he finished getting ready. No biggie. Once inside, he insisted that I see his "dungeon". The unit itself was pretty empty, minus a TV and couch, but his bedroom was fully kitted out. I was already creeped out, but then he took it one step further. I was appalled by what he asked me to do next.

He asked me to see if the shackles on his bed fit me. Thankfully, I had set up for a friend to call me within the first 30 minutes of the date and I faked an emergency.

Hotel HorrorsShutterstock

29. Showtimes of Sadness

Back in middle school, my mom drove me to meet a girl at an outdoor mall to see a movie. It was an hour away and my date canceled on me fifteen minutes before. I felt so bad for my mom driving me all the way there that I pretended everything was fine. My mom dropped me off, and I watched a movie by myself. Almost cried but I kept it together.

Embarrassing datesPexels

30. Number Two Secret

Second date but the first time at his apartment. After a few hours, disaster struck. Normally I’d never go number two at someone’s apartment but it was an emergency. The toilet wouldn’t flush and I ended up wrapping it up in toilet paper and hiding it in my purse! I slept over and the next morning the entire apartment stunk. He never found out thankfully and blamed his roommate for the smell.

Embarrassing datesPexels

31. Drips Of Love

I met a girl through mutual friends, and we drifted in and out of each other’s lives for a few years. I finally asked her out, and we had a romantic dinner at an outdoor cafe. It was a beautiful late summer evening and everything was going really well. We head back to my place and start kissing on my bed when I feel something warm drip from my nose.

I was having a nose bleed and it was already dripping on her upper lip. I was horrified and tried to wipe it off my face, and hers, which just smeared it, and then ran to the bathroom for kleenex and a washcloth. She was polite but promptly informed me that she was leaving and wouldn’t let me walk her to her car.

As she walked out the front door, she turned and said, “It’s really too bad, because I was in a REALLY good mood tonight". Then she was gone, and I headed to a bar to drown my sorrows. Somehow we’ve been together almost 10 years and married for six. Love you, sweetheart.

Embarrassing datesUnsplash

32. A Whole Mess

When we went back to my house after a bike trip, she fell and broke her cervical spine. I had to take her to the ER I work at—she got admitted and put into a halo in the ICU. I met her family there. We dated for something like nine months after that, but then she totally ghosted me. Months later, out of the blue, I got served by a sheriff—she was suing me for a million dollars over her injury.

It went on and on and even to trial. It came out she had lied to me and was still married when she went on date with me. Worse yet, she ghosted me because she was also cheating on me with another guy and she was pregnant with him at the time. He even testified about her disability at the trial.

Heartbreaking HospitalShutterstock

33. At Least She Didn’t Feel Awkward

When I was in high school, I went on a date with a friend of a friend. We went and saw a movie, then went out for dinner. I was nervous and awkward, and it ended without much fanfare. The date went OK, and there wasn't a second one, but that's not the bad part. About a month later, I went to a party at our mutual friend's house.

I saw her there and was afraid it might be a little awkward. I had no idea she was invited. About an hour into the party, she came up and started talking to the mutual friend, while I was standing nearby. After a few minutes of talking, the girl I had gone on a less-than-awesome date with came up and introduced herself to me.

Meet The Parents FactsShutterstock

34. Truth Is Subjective

I invited a girl from Tinder over to my house after a very steamy conversation (led by her). After bringing her to my place, she proceeded to absolutely ignore me and at best give me one-word answers to every line of the get-to-know-you conversation, acting like I was inconveniencing her by taking her attention away from her phone.

Any time I tried to make a move, I got shot down instantly. This went on for a few hours, so I put Netflix on. Big mistake on my part, apparently. Just as I was about to say it was time to leave, with no warning whatsoever, she straddled me and started aggressively making out with me. It was disgusting—a bunch of food residue from her mouth got into mine. She hadn’t brushed her teeth.

I noped out of that and we had a very quiet drive back to her house. Before I even left her driveway, she was texting me saying how great it went and that she wanted to see me again soon. Needless to say, that did not happen!

Most Embarrassing MomentsShutterstock

35. You’re As Old As You Feel

I went on a date with a guy on Bumble. We made plans for him to pick me up and go to a local restaurant for dinner. It ended up snowing the night before and the road had developed a layer of ice on top. I suggested rescheduling, but he insisted. He picked me up, and when leaving my neighborhood, he started to slide on the ice. My life flashed before my eyes and we ended up rear-ending the car at the end of my road.

Thankfully, everyone was okay. I was pretty shaken up, but we continued on with dinner and the rest of the night was pretty mild. The following Monday, his insurance ended up calling me, asking what happened. I called him to say I didn’t want to get any further involved after having spent forever on the phone with the adjustor and he responded by asking me out.

Not only that, but he ended up standing me up anyway. He claimed, “in his older age” he tends to be more forgetful…He was 27.

Amazing Coincidences factsShutterstock

36. Judgmental

I had to pick him up and he complained about car, the way I drove, my music tastes, why I was being so quiet, etc. But the moment that definitely did it was when he said, “My friends really want to meet you. I need them to know you’re real". That’s when I bounced.

Need to Leave Now factsShutterstock

37. Not A Family Guy

He invited me and a friend to play dodgeball with a group of folks I had never met. We were having an okay time—he was paying more attention to his friends, but that was fine because I had my own friend to keep me occupied. We were hanging out in the parking lot before the first game was about to start when, out of nowhere, he grabbed a ball and threw it at my crotch as hard as he could. He then screamed: “Wham, bam, right in the clam!”

I immediately turned to my friend and asked her if she was ready to leave. I said goodbye to him at that point. When I got home, I checked my phone and it had been blown up by multiple texts about how “immature” I was behaving.

Cheaters ExposedShutterstock

38. One Thing After Another

I went to a bar and met up with this cute girl. We got along pretty well. She invited me back to her place, but she eventually met up with friends at the bar. Near the end of the night, they were all tipsy, but her friend was insisting on driving home because she was very set on not leaving her truck parked outside a bar overnight.

So, I offered to drive her truck home. We got all the way to their apartment complex but getting into the parking spot was tricky. The friend who owned the truck then insisted on parking it for me. She essentially pulled the "I legally own this vehicle" card on me. Since I was just some guy her friend just met at a bar, and it was technically her truck, I was like, "...Okay then".

Within five seconds, she immediately regretted her decision. She backed the truck into a drainage ditch and got it stuck. We all had to push the truck and we got covered in mud. While we were doing that, the girl I met at the bar had lost her wallet, so I dug through the mud and water-filled ditch to find it. We got back to her place and the mood was definitely ruined, so we ended up eating a random cheese and meat platter from Safeway on her kitchen floor at like 4 am.

I slept on the couch, then woke up early the next morning and I thought to myself, "Well, she was great; it was just the whole truck thing that ruined it". I looked for a pen and paper to write down my number before leaving, but all I could find was a piece of paper taped to the inside of the door. It was a court date notice for a domestic case hearing. I just left and chalked it up as a strange night.

911 CallsShutterstock

39. My Crazy Ex-Boyfriend

To start our date, we first went for a walk. He did not shut up for an entire hour, complaining about everything and everyone in his life. He didn’t even ask me anything about my life. We eventually got to a restaurant, sat down, and he ordered food for me without asking what I wanted. Also, when he got his drink, the bartender mentioned the caps are difficult to open, but he arrogantly and rudely brushed him off.

He tried to open it himself but ended up spilling juice all over himself.  He then yelled like it was the staff's fault. He literally had no regard for anyone, just yelling. At that point, I wanted to get under the table because I was so embarrassed. He continued to talk about how superior he was, saying that when he became manager, he would fire people like the bartender.

At the end of the date, I offered to split the check because he mentioned he had money issues. I obviously did not want to see him ever again, so I did not want to feel like I owed him anything. His reaction made my blood boil. He yelled at me, causing a scene in front of several diners. I left the money on the table and walked off.

He continued to yell at me for going after the check.  He grabbed my hand and angrily told me to wait for him. When I said I would just grab a taxi home, he forcefully insisted on walking me home. To avoid him making another scene, I accepted. We walked in silence, so I tried to break off from him and leave, but he insisted on following me home because he thought there might be some dangerous people around.

I was already creeped out at that point, but when we got to my front gate, his horrendous actions solidified my fears. He tried to force himself on me. I said, “I don't think this will work". His exact words were, "You owe it to me. We went on a date, and I did not waste my money for nothing".

When I pushed him away from me, he threw a $20 bill at my face, then said, "Here, we are done!" I instantly got into the yard and locked the fence. I could still hear him yelling, so I sent him a text saying I would call the authorities if he did not get out of there. He finally left. The worst part was his aunt was our neighbor, and my mom knew his mom.

The next day, on my way out, she literally had the audacity to ask how it went. I just told her, "You should have raised him better". They never spoke to me again. I was absolutely fine with that.

Dealbreaker DatesShutterstock

40. You’re Focused On The Wrong Thing

My date phoned me the morning before our date at 2 am to say she was so excited about our date. Then, mid-conversation, she crashed her car. After that, I didn’t hear from her until the date—I had to pick her up at that point because totaled her car. The date started well and I took her to a fancy sushi place, but she did not eat one piece as she was talking the entire time.

I slowly established that she had not slept for a few days and her eyes were rolling. I settled the bill and took her home to a very judgmental roommate. As I was walking back to my car, I heard a bloodcurdling shriek..." Where is my goodnight kiss?!" My anxiety kicked in and I started running to my car. I looked back and she was chasing me, still screaming.

Neighbors from all over her complex started watching from their homes but I somehow managed to escape. Months later, I ran into her roommate out on the town and she said, "Oh yes, you were the one who ate all the sushi".

Creepy DatesShutterstock

41. It’s Too Much

I met this guy Ron on OkCupid. He seemed nice enough, even though he was older than his profile said. We chatted over the phone a few times and he came across okay enough to meet. So, we did. I went to his house for the first meeting because I was honest in telling him what wouldn't be happening. I figured he was gentleman enough to respect my wishes.

We chatted for a while on his back porch and watched a movie in his living room. But then he started to act weird around me—he would grope me and I reminded him that wasn't happening and to please stop. "You're just so beautiful, I can't help myself". He could help himself. I was suddenly "very tired" and wanted to head home. He started texting me, just constantly bombarding me with compliments and it was smothering.

I talked about boundaries with him, but he just ignored me. He even offered me a key to his house. so I could pop over anytime. He wanted to get a dog so I could come over and walk it while he was at work. He also mentioned a work trip to Hawaii several months in advance and told me he wanted to take me. I started to pull away from him a little and explained that he was being too much too fast.

After a long break, we decided to meet up again because I make bad choices sometimes, admittedly. Things just got worse from that point on. He started touching me again, smothering me. He legitimately would not leave his hands to himself, so I leaned forward on my knees so he couldn't touch me. I told him I was leaving and he walked me back to my truck because it was late and dark.

He hugged me and wouldn't let go. I tried pulling back and telling him to let go, panicking, but he wouldn't. I started to nervously laugh because I was in full panic mode. I opened my door and he stood beside it, not letting me close it. I couldn't drive my car forward because I was in a parking garage and there was a car in front of me. If I go reversed, my door would have probably gotten torn off.

When I went ballistic and screamed at him to move, he backed up, made a snarky remark, and I finally went home. He started texting me again—long, long paragraphs about how when I "hugged him" he felt sparks he'd never felt before, how I mean so much to him, and how he's never felt this connected. I just stopped responding.

He started texting me more, I don't answer. Then he got mean, but I still didn't answer. I headed to work the next Monday and showed the text messages and his face to security and told them to not let him on campus. Security couldn't believe the text messages. I learned my lesson BIG TIME with him.

Glitch In The MatrixShutterstock

42. What Did I Say?

I met a girl through a friend at a party and we went on a few dates. On one of them, we ended up at a hotel and decided to stay the whole weekend. The last night, after a few drinks, we were chatting under the sheets. Drinks, snacks, good times. Suddenly, she switched to a whole other conversation. Not a simple switching of subjects, either.

This was a quick and smooth transition from a real conversation to one that was between her and…someone else. I was confused, but I brushed it off. This happened a couple of times. The third time though, I had to say something; I couldn’t just let it go. It was horrifying—she was weirded out and was just as confused as I was when I listened to the things she said.

I told her it was like she had parallel conversations going on in her head. She became visibly frightened by herself and nervously panicked, ultimately breaking down and thinking she was crazy. I tried to comfort her until we fell asleep. I found out later she was diagnosed bipolar, but never really heard from her after that night.

Cranky Customers FactsShutterstock

43. Strongly Opinionated

I went on a date with a girl who suggested a restaurant but it was closed when we got there. She told me it was where she'd had her wedding reception after marrying her much older husband. Then, at the next restaurant, she revealed her true colors—immediately asked me how I felt about Trump while telling me how great she thought he was before I answered.,

Then she drank most of the bottle of vino we ordered, made rude comments in the restaurant out loud, and told me constantly that she made more than I did (I'm not sure if she was right, but it was a weird thing to care about regardless). She told me she forgot my name twice and spent the entire car ride back to her place trying to convince me Obama's birth certificate was a forgery.

Dealbreaker DatesShutterstock

44. Older, Not Wiser

I was 18 with a Plenty of Fish profile and I got catfished by this dude who was about 20 years older than me. We met at Starbucks and upon seeing him, I knew I was out of my depth, but I didn't know what to do so I went along with the date. Worst decision ever. He would ask me my interests and then shoot them down. For example, he'd be like: “You're into Harry Potter? I think that is so childish!”

I knew I needed to nope out of there, but he kept insisting I come over to his place. He used the fact he bought me a coffee to make me feel guilty. I agreed to go to a park but that was the most he was going to get. I said I had to drive separately as I had to go somewhere later and during the drive, I called a friend and asked her to call me in fifteen minutes to give me an excuse to bail.

At the park, he mentioned that he knew he was older and attributed that to my "strange" behavior. He found it so odd that I did not want to see his house—he explained that he only invited me because he felt a connection and knew I wouldn't want to meet him if I knew he wasn't like his picture anymore. Not long after my bailout call came, he became so cold and it was scary.

Thankfully, I slipped off after a very awkward hug.

Creepy DatesShutterstock

45. The Divine Plan

I went on a first date with a guy after meeting him on a dating site. The phone calls went well so I thought, why not. We met at the mall. Right off the bat, I got a weird vibe. He proceeded to tell me how many kids we would have, and how he would hit them whenever they were disobedient. The guy was fully serious, too—he said we had to do it because "it’s what God wants".

He ended up following me to my car and I was thankful it was daytime in a busy mall with a security guard watching.  He then tried to make out me, but I slapped him and drove away.

Drivers Share Their Craziest Experiences On The RoadShutterstock

46. No Game

He was 45 minutes late picking me up, but the weather was quite poor, so I gave him a pass. When we got to the coffee shop, I took off my jacket, and he immediately uttered a sentence that made me feel super uncomfortable “I see you brought your A-game, or should I say, D-game,” referring to my chest. Even the people two tables over just stopped and looked at him.

Horrific Birthday FactsShutterstock

47. Pet Peeve

She brought her pet rat with her. It was hanging out in her bra and she fed it French fries. She also casually mentioned she had warrants, so I just faked an emergency and bailed.

Animals’ Biggest Power Moves FactsShutterstock

48. Slashing Good Time

He brought two friends along, which was unexpected. They were all drinking. I flagged down a waitress while one guy left to go do something. As I ordered my food, my date, and his other friend confessed they'd already eaten. Then the third guy walked back into the restaurant and when I saw him, I gasped. There was blood dripping from a horrific gash in his arm.

In shock, I ran to my car and grabbed my first aid kit, then cleaned and butterflied the wound. I put bandages on his arm and had the guy elevate it while the waitress called an ambulance. I got cleaned up and returned to find the other guys had just eaten my food. I grabbed my kit and my purse and walked out.

2017 FactsShutterstock

49. Netflix And No Chill

She turned out to be just a nasty, rude person. Maybe she had a bad day, who knows; but she said something that just made me lose all patience with her. We went to a cool-but-not-expensive hipster restaurant on a Friday night and they were busy. She complained the whole time about the service being slow, saying that they were stupid for having a hard time understanding her over the loud noise.

She made fun of the other customers, but not in a clever, observational, "Larry David" way. She was just senselessly mean and petty. The breaking point, however, was when she made a shocking comment about my appearance. She probably intended it to be some sort of flirtatious shade, but I took it personally. I wolfed down my food and then signaled for the check.

I waited for an agonizing five to 10 minutes for it to come. I stood up, threw down enough cash for my meal and a generous tip for both of us (she’d been such a monster to the servers that I knew she wasn’t going to tip anything), and I started putting my windbreaker on.

She asked me, “Are you cold?” “No". “Oh. Where are we headed next then?” “Home". When I said that, she looked confused for a second, then gave me a coy look and said, “Oh OK, yeah, I’m down for Netflix". Realizing what she thought I was implying, I just said, “Oh, no, I meant I'm going home...alone". Off the patio, I went right into the street.

Date Fail Experience BehemothShutterstock

50. Uncontrollable Urge

He was a friend of a friend. He went to a restaurant and ordered our food. While we waited, he started to say things like, “First I’ll eat this meal, then I’ll eat you". I laughed because I thought he was just joking. I thought he was just nervous and his mouth lost its filter. Then, when the waitress asked if we wanted more to drink, he was like, “Yes, bring us something strong".

I said not for me since I had to drive later and he looked at me weird, saying, “Don’t be stupid. Do you think I’ll do you once and let you leave? You’ll at least stay the night". The waitress looked at me with wide eyes like I was crazy for even being there. After she left, I told him that he had to stop with this—I said he was being rude and that we were only on our first date.

He apologized and for about 10 minutes it was okay. Then, as if a switch was flipped, he went back to being a monster. “You know what, I can’t control myself anymore. Either we go now or I’ll put you on this table". I told him I had to go to the bathroom. I silently went to the waitress, paid for the food, and left without a word.

Awkward DatesShutterstock

51. It Was You—Not Me

I was on a mediocre date, walking back to her apartment. On the way, she took a phone call about a couch she was buying. This call continued for the next few hours. She insisted I stay and put on Netflix while she was on the call. After she hung up she said, “There isn’t going to be a second date, is there?” I agreed there would not.

Embarrassing datesPexels

52. Good Instincts

My date and I met in a park and were walking around getting to know each other. He suggested walking into the woods, and I said no because it was the first time I had met him. He was immediately offended that I didn’t trust him. It wasn't personal, just common sense on a first date. Against my better judgment, we continued to dinner. I should have listened to my gut.

The restaurant brought him the wrong food and he was very upset and angry about it. At the end of the meal, I wanted to split the bill and was so anxious to leave I had trouble with the math. By accident, I tipped more than I intended. He was again immediately offended. Never saw each other after that and I’m still cringing.

Embarrassing datesPexels

53. The Wrong Film

The guy was hot and interesting, so I invited him over thinking we’d have some casual fun. He arrived and it was going fine—we had loads in common including film taste. We decided to watch a movie and settled on Nymphomaniac, which neither of us had seen or known much about. Little did we know what we were getting ourselves into. 

It was a very disturbing film for various reasons, awkward and painful viewing. It totally ruined the mood. We finished the movie and mutually decided to end the date. I didn’t bother to arrange another date.

Embarrassing datesPexels

54. Oldest Trick In The Book

I got to the restaurant first and waited outside. When he arrived, he was extremely energetic past the point of being normal. When we sat down, I could see his eyes were dilated and unblinking. I assumed by that point he had done some sort of substance before the date. We agreed to have one drink at the restaurant, then go somewhere else for food.

During the drink portion of the date, he told me he could get me a good job selling cars at his business and then asked me to move in with him to annoy his ex-wife. I just chuckled and brushed it off. I told him I'd meet him at the restaurant and he shocked me with his next move—he followed me to my car, got in on the passenger side, and wanted me to drive him there.

I was a little freaked out but I tried to roll with it. We got to the restaurant and the vibes were all off at that point. I was significantly freaked out, so I used the bathroom excuse to ditch him and leave. I got to the front and realized I left my purse behind, so I asked the hostess for help. I told her to please find a way to get me out of the date. Fast forward about ten minutes and a glass of pinot later.

The manager came in making his rounds to the tables, stopped at ours, and asked for my name. He said I had a phone call up at the front. Not the smoothest line, but I went with it. I told my date I'd be right back, then grabbed my purse and hightailed it out of there.

Unforgettable Customer Service MomentsShutterstock

55. It’s Shark Week Every Week

She had a weird obsession with sharks. She had shark decals on her car, shark tattoos, and wouldn't talk about anything but sharks. After lunch, she revealed she had no money, so I had to pay. I was going to anyway, but for her to bring no money on a date and just presume I would pay was pretty insulting.

Deep Sea DivesShutterstock

56. Multi-Level Madness

We met up at a café. Within the first minute, he pulled out a bunch of brochures and started telling me how amazing Amway and its products are. He told me all about how you could gain access to all kinds of cool events and stuff by becoming a sales rep, etc. I was pretty annoyed that I was scammed into an MLM pitch meeting and I told him so.

After I said that, he completely lost it. He got extremely angry and defensive. He said: "I'm not trying to recruit you! I knew you were from Michigan and Amway was founded there, so I thought it'd be a good topic!" Right. I told him I was leaving and asked the waiter for the check. The dude literally then screamed: "SEPARATE CHECKS!" at the waiter, drawing the attention of everyone in the cafe.

I started getting a bit freaked out and was scared to walk to my car because the dude was literally shaking with rage. I was terrified he'd try to follow me, so when we went outside, I remained standing by the café door thinking he would walk ahead to his car first. Nope. Instead, he took it as an opportunity to stand there and scream at me in the parking lot.

H was still insisting he wasn't trying to recruit me and said I ruined the date by accusing him. As if somehow him yelling at me in a parking lot is going to change my mind. Finally, I couldn't take anymore—I just went to my car, locked the doors quickly, and drove multiple circles before going home.

Waiters Witnessed Disastrous DatesShutterstock

57. If The Shoe Fits…

I was taking part in a college "Cinderella" activity where girls put one of their shoes in a pile. A guy would pick a shoe and he'd go out on a date with the girl who the shoe belonged to. My roommates and I all did it as a group and it was supposed to be fun...until the weirdest guy picked my shoe. I honored the activity and went on the date, which was at a bowling alley.

Every time I got up to bowl, he would shout at the top of his lungs like: "THAT'S MY DATE!" He also shot put the bowling ball and probably ruined the lane. Sometimes his throws were so bad they would go down someone else's lane. At one point, he tried to kiss me in front of everyone...It was terrible.

911 CallsShutterstock

58. Just Make A Decision

I matched with a girl on Bumble and we talked over the course of a few weeks. We made plans to meet u one weekend. I texted her the day before to see if we were still on. She didn't reply until the day of. She said that she actually had somewhere to be later in the day, but asked me if I wanted to get coffee before then.

She also asked me if I could pick her up because her car was in the shop. I said yes to both, like a true idiot. She asked me if I knew of any places we could go. I said there was a Starbucks in my area, but she asked me if I knew of any places other than Starbucks. I went on Google, found a neat little local coffee place, and threw that one by her.

She didn't respond for 45 minutes. I ended up sending her another text asking her how that sounded. She replied back that it sounded good, but the place was closing within the next twenty minutes. I went back to Google and found a different coffee place in her area that didn't close for another two hours. I threw that one by her and then she texted back asking if we could take a raincheck.

I said, "Sure," but didn't have much intention of reaching out to her again. She had already flaked twice before and the fact that she basically ended up wasting most of my afternoon kind of dampened my interest a bit.

Online Dating EditorialShutterstock

59. I Spy

We were having great chats online, so we decided to meet in person. He showed up wearing a Bluetooth headset with a little LED light that indicated it was on. He kept it on during drinks. I worked up the nerve to ask if he could take off the headset while we were eating dinner.

With pride and complete confidence, he gave a response that sent shivers up my spine. "Don't worry! You totally have my full attention. This isn't a phone headset, it's a camera".

HR NightmaresShutterstock

60. Expensive Taste

I went on a first date with a girl who insisted we go to a really expensive place. When we got there, she ordered a $25 appetizer, a $45 steak, and a $15 drink. She wouldn't put down her phone and she kept taking calls and answering texts. The waitress noticed and motioned for me from behind her. I excused myself, and the waitress had separate bills all made up.

She then asked if I wanted to pay my share and leave her at the table. I said, "That would be wonderful!" So, I did.

Creepy DatesShutterstock

61. If You Invite Two Friends

Back in high school, there was a very beautiful girl named Melissa in a few of my classes. This was in the late nineties, and pregnant teenagers weren't as common as they are now, so I think it added to her mystique that she had a child. It never bothered me, though. I just thought she was the most beautiful woman I had ever seen. So, any chance I got to be around her, I took it.

She needed a tutor? Check. Someone to talk to? Check. I never had the guts to ask her out, though. I wasn't much of a looker myself in high school, so it took me a pretty darn long time to do it. Finally, I did, and she said yes! I can't remember how it went down, but I think we decided that I'd pick the restaurant and she'd pick something else to do.

It was all great until she showed up on our date with a totally unexpected surprise. She brought her sister along with her. That should have been my cue to just go back inside my house, but I didn't because I was an idiot. We went to eat, and then she said she had a "surprise" for me that she thought I'd really enjoy. I was excited; did she really plan something?

We pulled up to a small convention center and started to head in. I was already starting to wonder what we were doing as we made our way towards one of the rooms, and there it was...clear as day on a sign out front of the door—a pyramid scheme. I cannot describe my internal anguish and feelings of absolute fail during the lecture and the meet-up afterward.

They didn't even sit with me. We'd arrived late, and they moved to open seats on one side while I sat on the other. I barely remember how I answered the inundation of the people's questions, but somehow, I made it through the evening. I remember never even seeing Melissa or her sister during this time, and when we finally met up to go home, I was utterly destroyed.

When we got home, she looked me straight in the eyes and told me that she had a really nice time that night. I echoed the sentiment, told her sister it was nice to meet her, then went inside. I never even looked at Melissa again.

Cheaters ExposedShutterstock

62. Thanks But No Thanks

We started chatting online. At the time, I was a smoker and I told him this. He said it was no big deal because he smoked too. One day, we decided to meet up at Starbucks for coffee. The first thing he said was: "Hi. By the way, when I said I smoke, I was talking about the hard stuff". I said, "Oh. Bye!" then turned around and left.

Crushes Gone WrongGetty Images

63. We’re All Confused

It was our third date and we decided to go to a club. It was getting pretty late so we ordered a Lyft to beat the crowds of people trying to exit at the same time. We exited the club and someone pulled my arm hard when we got outside. I turned around and my face went white—a random guy was accusing me of ghosting him and leaving him at a club with the bill.

I told him he had me confused with someone else which only made him more and more upset. He kept reaching and pulling at my arms. My date pushed the random guy away and pulled me closer, which only set him off even more. Security noticed and thought we were causing an issue with the dude. My date tried explaining what was going on and the random dude lunged at me.

I remember I had my taser with me, so I took it out and laid it on him. He fell to the ground, confused. I'm pretty sure he mistook me for someone else, but that was terrifying.

Taxi driversShutterstock

64. Third Wheel

I had been talking to a woman for a couple of weeks and she ran hot and cold. Mostly cold. I was thinking about moving on from her, but then one lonely Saturday night, she called and invited me to a bar for a few drinks. I told myself, why not, and went. when I got there, she was with one of her girlfriends. Her friend was a late 20-something and chatty as anything.

Immediately, I could tell my date was far more interested in her friend’s welfare than in me. It later came out that the friend’s husband was a jealous weirdo. I played along, had a few drinks, and listened to the friend vent her problems, but it was clear I was not part of the night’s festivities. Whatever. It was better than being home alone on a Saturday night. Then, an hour or so later, things got interesting—the weirdo husband showed up.

He charged up to our table, whipped out a camera, and took a picture of all of us. He muttered some vague threat to his wife before leaving. The friend got super upset and decided to go home. My date wanted to walk her out and we went outside to say goodbyes. She walked away and I turned around, thinking finally I got my date to myself.

Then I see she'd already hopped inside her car. She drove off without even a wave goodbye, leaving me all alone. I went back into the bar had a couple more drinks hoping to meet someone, but I suck at bars. I went home an hour later.

65. Too Much, Too Soon

I met a guy online about 20 years ago. He was really smart and funny, so I gave him my number. I really enjoyed talking with him. I’m 5’7” and he said he was the same height. I was in my early 20s and he said he was in his early 30s. We decided to meet up on a Saturday morning and go to the flea market which was huge in our area at the time.

When we finally met up, I shook my head in disappointment—he was only 5’4” and in his early 40s, easy. I was mad that he had lied to me, but I really liked him and decided to continue with the date. It was my first time meeting this guy face to face, and he was all over me. Kissing me, hugging me, holding my hand, and I had a difficult time walking around because he was literally attached to my side.

It was just way too much. After the market, he wanted me to come up to his hotel room. When I said no, he was hurt and disappointed. I’m grateful that he didn’t get angry and abusive, but at the time, I couldn’t get away from him fast enough. He quickly moved on.

Petty Revenges factsShutterstock

66. Entertain Me

I showed up for a coffee date and about five minutes in, I knew it wasn't going to be a fit. But I figured hey, might as well be polite. After about fifteen minutes of trying to make conversation and getting back one-word responses, I paused. I told her that part of my job was to talk with all sorts of people and that I was struggling to keep the conversation going with her. I then asked if she was okay.

I was legitimately concerned for her because her behavior was so abnormal, and plus, the anecdotal evidence is that I'm a fun and easy date. Her response was chilling: "Oh it's just funny watching you struggle". I stared at her for a few seconds, then told her she was a terrible person and left. I still shake my head at that one.

Worst Dates factsShutterstock

67. A Journey

I started chatting with this girl on Tinder. She was cute and we got on really well. I asked her out for a drink and she said sure. As I was getting ready, she texted to say she was running a bit late. Fair enough—I figured I'd go on time, grab us a table at the bar, and have a cheeky pint to calm my nerves. When I got there, she asked if I could just meet her halfway.

Since it was getting dark, I agreed to meet with her. I was walking and walking but there was no sign of her. She kept texting me updates, telling me which roads to turn on and whatnot, but I was starting to feel a little uncomfortable with it all. Eventually, I came to a house. I hesitantly knocked on the door and some chick in nearly see-through leggings and a matching black top opened the door.

She looked nothing at all like her profile and I felt I'd been catfished. She welcomed me in saying she'd just be a few more minutes and we can go. Me being me, I decided to be polite and play along to the end of the night knowing full well I was never going to talk to her again. We went inside where she then had a screaming competition with her mom and stormed off to her room.

I awkwardly followed, and when I entered her room, I discovered her secret—she was a massive hoarder. Her room was a mess. In the middle of her bed, there was a half-eaten kebab. She invited me to join her and I awkwardly sat on the edge of the bed while she ate it. After chatting for a bit, I mentioned going back out for that drink but she said she wanted to stay in.

When it started to get late, she tried to make several moves on me but I politely turned her down. I excused myself to go to the loo, noped it out the house, and went home. When she realized I'd gone, she texted me a bombardment of nasty messages and threatened to come round mine with a bunch of her mates and hurt me.

I ignored it until she texted me my own address (which I'd never told her) and said she'd see me in a few. Thankfully she never turned up!

Juiciest Gossip factsShutterstock

68. On Thin Ice

I went on what was supposed to be a simple coffee date, but our shopping center was hosting an ice rink that she absolutely wanted to go to. I have poor stability even on solid ground, but I thought maybe a bit of messing around on an ice rink would make her laugh. Nope. Within seconds, I slipped and outright twisted my ankle and wrist.

I needed help being carried out to sit on a bench and try to recover. But here's the kicker—she couldn't care less and continued skating by herself, attracting the attention of another skater. I watched the two of them leave without her even looking back to check on me.

Worst Dates factsShutterstock

69. Stalker

It seemed to be going alright for a while. One afternoon, we went for a stroll around town, doing a little bit of a pub crawl with a drink at each place, followed by some food at a monthly food truck festival that I knew about. All this was going to be followed by a local bar and dancing. The entire time, I kept seeing the same guy at all the locations who was obviously following us.

On a toilet break, I mentioned something to one of the pub doormen and he asked the man to leave politely. My date noticed what was happening and she suddenly ran over to the doorman. I was so confused until she spilled the awkward truth—it was her husband. They had a kink of watching each other go out with someone and maybe watching them hook up.

I left them with the doormen and reported them to the authorities.

Oversharers Went Too FarShutterstock

70. Weird Pal

I was talking to a guy who was a math professor. He invited me on a date to an outdoor play where he was playing an "important role". I showed up to see it was a church picnic and he was playing the devil. He introduced me to his family and all they talked about was Weird Al. Like, they didn't listen to anything BUT Weird Al.

Then, his sister loudly interrogated me about why I went to a private school. Unbeknownst to me, he had told them everything about me and every conversation we ever had. I faked an emergency to get out of there. Later, he asked me out on a second date and he said he wanted to take me to the state fair with his whole family.

Nostalgic People Describe the Most Memorable Trends of the 2010sGetty Images

71. Dinner And A Show

There was a girl in my IT support training session and she knew so little about computers I was positive she walked into the wrong class and just stuck around. I figured maybe she just wasn’t used to working in an enterprise-level company and maybe she was just out of her element. Either way, I didn’t think she was sticking around so I asked her out.

I later found out that she was an aspiring actress and not a computer professional at all; she just wanted to see if she could play one. The date wasn’t so bad but shortly after the food arrived, her behavior became startlingly weird—started playing with her food. I mean, full-on making sounds while playing with it. I noticed, then made a comment like, “Don’t play with your food,” as a joke.

But she just glared at me then went back to playing with her food. I think I gave her the benefit of the doubt for long enough at that point. She was really attractive which was why I probably looked past everything...but when she started singing to her steak, I kind of just gave up.

Worst Dates factsShutterstock

72. Fate Can Be Funny

I finally went on a date with a guy from work who had asked me out about 20 times. It was as awful as expected. He would sit silently staring at my chest then suddenly blurt out some ‘fun fact’ before going back to boob-watching. So, I went to the loo and climbed out the window; except, the worst-case scenario happened—I got stuck. So stuck that the restaurant had to phone for the fire brigade to get me out.

My date had come into the bathroom to watch, but all he did was keep staring at my bum, trying to touch it. The firemen threw him out so he went round the back of the pub (where my top half was sticking out) and tried kissing me there. As my arms were through the hole, I managed to land a right hook on his face.

The firemen made him leave. When I saw him at work the next day, he had a massive black eye and told everyone I had freaked out and injured him! About three years later, I met my now-husband.

One date night, whilst out with friends, my husband was asked about funny moments at his job. Coincidentally, he is a fireman. He told the story of a woman who was trapped in a bathroom window trying to escape a date!

Embarrassing kidsPexels

73. Ah, Young Love

One time in the eighth grade, I finally got the courage to ask this girl out. She just so happened to be the friend of my best friend’s current girlfriend, so we decided to make it a double date. During the movie, everything was going as planned. I sat by her while my friend sat with his girlfriend. Then we saw a couple of her girlfriends walk into the theater.

They happened to see the girl I was with right away. She then motioned with her hand for her friends to come over there. When her friends got to where we were sitting, the girl I asked out turned to me and asked, "Can you scoot down a seat so I can sit next to my friends?" I said sure, so I got up, and just walked out of the theater.

Creepy DatesShutterstock

74. No One Had Fun That Day

The girl was totally normal, nice, and well-mannered. It was the circumstances that made it awful. We decided to meet at this bar/grill with a big outdoor patio in the late afternoon one weekend. We got there and the place was PACKED, so the hostess sat us at a small table for two. As soon as we sat, we heard an older woman say my date’s name in kind of a shocked tone.

My date turned her head and her face dropped. It was her MOM! Her mother just happened to be there getting some drinks with friends, so we had to spend our whole first date making chit-chat and sipping our drinks with her mother about five feet away.

Worst First Date FactsShutterstock

75. Red Hot Love

I once invited a girl I liked a lot to see a movie and she agreed. We chatted about this and that before the movie started and out of the blue, she mentioned her boyfriend. I kept talking as if it was no issue, but halfway through the movie, I excused myself to the bathroom. I walked out and planned to never see her again.

She called me about a week later saying had lied about the boyfriend because she was nervous. I liked her so much that I decided I would give her another chance. On the second date, it didn't get any better. She told me she was a volunteer firefighter which was cool. But the only thing she was interested in was... fire. "Have you ever seen a house burn? It's so beautiful!"

Fire this, fire that on and on through the evening. Every time I tried to draw the topic away from fires, she found a way to come back to it. Needless to say, I never called her again!

Unforgettable callsUnsplash

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

We were getting it on and he launched me out of bed. My head broke the fall. I kept blacking out so he took me to the ER. As I was sitting in bed with a neck brace on, awaiting tests, he asked if he could see me again. I just stared at him. Twelve hours later, I was released with a severe concussion. The doctor asked me to take a month off of work.

I couldn’t do that so she lowered it to a week if I agreed to sleep during most of it. So, for seven days, I was on medication that knocked me completely out. I would wake up long enough to eat, drink some water, pee, and take more medication. The adult cuddling wasn’t even that good… and no, I never saw him again.

Doctors Knew Lying FactsShutterstock

77. Not In Your Future

She claimed that she could see angels in three different colors. Apparently, during one of her "encounters," the angel was covered in dark scales, with red glowing lights coming out from her skin underneath. The angel came to her in the middle of the night, crawled to her bed, then placed its hand on her shoulder in order to cast an evil spirit out of her room.

If that wasn't creepy enough, she then said that while I was in the bathroom, an angel came to her and informed her of my chilling fate. She said she knew when I was going to die and how it would happen. I told her I'd be right back, saying that I left something in the bathroom. But I left instead, completely creeped out by her. I still wonder what strange stuff she was getting into.

Abandoned Places FactsShutterstock

78. Great Expectations

We met at the restaurant and I arrived first to get a table. Once she got there, she walked over to me, shook my hand, and I pushed her chair in. Then the server asked us what we would like to order. Ignoring her, she looked intently at me and asked a startling question: "How much money do you make?"  I said, "Excuse me?" in a confused tone, somewhat taken aback.

She stared at me and very slowly asked again, "How much money do you make in a year?" I looked over at the server who was still standing there with a really awkward look on their face and thanked them for their assistance so far. Turned to my "date" and said I was sorry, but I had to leave, and I got up and walked out.

Midsection Of Woman Holding WalletGetty Images

79. Three Of A Kind

I met a woman for a mid-afternoon meal. It was a nice day, so we sat outside. She was slightly odd but there were no major red flags...until she hit me with a huge surprise: “Hey, my husband is on the way with our dog. Come meet my dog". I thought, “Well, I wasn’t expecting this,” but by that time, he was already with us. We chatted for a bit, but I didn’t say much to the dog as it was all a bit embarrassing all around.

I paid the bill, made some excuses, and left them to it. He was a nice dude and deserved better.

Rejected Proposals factsShutterstock

80. Not A Match

I matched with a woman on Tinder and we hit it off pretty well. She was a “furry” and I am not, but she was pretty, and I was looking for something casual. Eventually, we planned to hang out at her apartment downtown. I got there and her place was incredible—like, she was obviously a wealthy woman and I was blown away by the unit.

We went into her living room and there was a guy there. Roommate? Nope. Friend? Nah. It was her boyfriend. Then, I had a cringe-worthy realization: it turned out this woman was polyamorous and didn't plan on telling me, a big no-no. I sat down and endured her trying to get me and the other guy acquainted, but he was wholly uninterested in speaking to me. No hard feelings though; the feeling was mutual. I dipped out in about an hour. It sucked.

Awkward DatesShutterstock

81. An Unsettling Turn Of Events

I met a girl online who was beautiful, fit, and smart, but a little older; only by about five years. She was a dentist and we had an awesome date. She came over and we did the deed—she scratched up my back and all, but whatever, it was great. That morning, I woke up to the sound of plates breaking. I ran downstairs and saw her throwing out all my plates into the trashcan.

I calmly asked her why she was doing that and she said I deserved better plates. OK, I suppose so. Then she asked to go upstairs and cuddle. That's when things got scary. She started whispering to me about how she lost her ability to practice dentistry and that she was not what she seemed. I laughed a little and started to get nervous. When I asked her if she was OK, She ran off to my bathroom and locked the door.

At that point, I was pretty terrified she was going to either use my razor on herself or on me. I heard the sound of canisters being emptied out and nervously asked what she was doing. She came out and says she made a mistake. She was married and has a child but she was not allowed to see her kid or stay at the house. At that point, I realized I was dealing with someone ill.

I told her to come downstairs and I'd cook her some eggs. I had no plates anymore, so I offered to take her out for a quick sandwich. We headed over to the place and not a single word was exchanged. I picked up both sandwiches and we ate them on a bench outside. She said thank you and called me cute, then left me there. She just walked away without a word and I didn’t hear from her again.

Creepy momentsPexels

82. The Art Of Pitching Woo

I was 10 years old and had a huge crush on my best guy friend who probably still thought girls had cooties. Being a hopeless romantic, I decided what better date to go on than dinner and a movie. My mother, as our chaperone, brought us to Olive Garden where I excused myself to the bathroom and proceeded to change into the only dress I owned.

Then we went out to the movies where I insisted that my mother and sister sit in a different row from us and, faking the damsel in distress, asked him if he would hold my hand if I got scared. Even better, when we dropped him off at home that night, to his horror, I kissed him on the cheek in front of his mom and older sister.

I then spent the next few YEARS being ridiculed about the whole event while his sister told the story to all our friends every chance she got. Needless to say, I embarrassed myself pretty well, and probably scarred this poor boy for most of his prepubescent life.

Cringe momentsShutterstock

83. Jokes On Him

I showed up at the pub and he looked only vaguely like his pictures. I thought well, I'm not really attracted to him, but maybe he has a good personality. As we went deeper into the date, I got my answer. He started asking me questions about my interests and then dissecting and belittling my answers. The one that I remember the most was, "What kind of movies do you like?"

I replied that I like comedies, to which he responded, "Oh, I only like documentaries because I actually can learn something. I surround myself with friends who are funny so that's where I get my humor". After several interactions like that, I just went home. I was surprised when he texted me asking if I wanted to hang out again. He does know how to be funny after all.

Most Embarrassing Childhood Memories factsShutterstock

84. A Whirlwind Romance

I excitedly met up with this girl at a bar and the first thing she told me is that my hair is gross. I take very good care of my hair; she just doesn’t like long hair on dudes. We got the pleasantries out of the way and then she went on to brag about how she'd been with several guys who were over six feet (I’m 5’8"). She then asked me to send her $30 because “These nails didn’t do themselves".

But that's not even the worst part. Continuing on, she started roasting me for living with my family even though she also lived with her family. At the end of the date, she asked me to sit in her car with her. I agreed and we talked for a bit. It got a bit too political, which I didn't like, but it was better than hearing about her escapades. After a while, she told me that she was leaving because some other guy had just arrived to pick her up.

Treat yourselfUnsplash

85. Three’s A Crowd

I once went with a larger group of friends to an outdoor movie festival that was happening in a remote place. You could only get there by boat, but it still attracted quite a number of people. The options were camping or a super expensive hotel. I was in college, so we camped. The place also had an outside bar and restaurant.

I was sharing my tent with my then-girlfriend and one of my exes had tagged along because we were on good terms and she was part of my group of friends. Fast forward to the first evening of the festival and we were grabbing dinner at the venue. I bumped into another of my exes. Being the polite person that I am, I said hi and asked her how she was doing.

She later sat down at the same table. Things were beginning to get awkward for me at that point. As I was finishing my food, guess what? Another ex showed up with her current boyfriend and sat down at the table. Mind you, at that moment, there was my current girlfriend and three of my exes sitting at the same table, along with some other people.

One of my friends decided to make things extra weird by very loudly pointing out the situation and ensuring everyone there knew who everyone else was. Needless to say, I had a freshly minted ex by the time the night was over.

Fake friendsShutterstock

86. Mistake Number One

I talked to this guy on OkCupid for about three or four days. I learned an important lesson after I made the mistake of telling him where I work. One night, he told me that he was going to the casino with his friends. In the morning, he said that he won some money and used it to buy me a gift because he really felt that this was going to be something special.

I told him I was uncomfortable with him buying me a gift as we had only been chatting with each other for a few days. But he didn't want to hear it—he replied that he was going to take the next bus and get off at the stop near my work. He told me to meet him there if I wanted the gift and if I felt the same way. I didn’t respond.

I also didn’t show up. When I left work for the day hours later, I saw him sitting at the bus stop with a brown paper bag in his hands. I blocked him and changed jobs. It was just a fast-food part-time thing during college, so I was easily able to find something else. I didn’t feel safe working there anymore.

Worst Blind Date FactsShutterstock

87. Memory Of A Goldfish

I’d been messaging a girl on Tinder for a couple of weeks. We even spoke on the phone some nights and she seemed pretty cool. We organized a date to check out a food market in the city and I offered to pick her up from her place. I let her know when I was on my way, but when I got there and let her know I was outside, there was no answer.

She lived in a gated apartment block so all I could really do was call and text. I must have waited out there for about 20 minutes trying to let her know I had arrived, but still no response. I went to grab myself a burrito near her place and she called me later with an update that made my blood boil—she told me she’d "forgotten about our date"… even though I literally called her like 30 minutes beforehand to confirm.

Anyway, she begged me to come back, and stupidly I obliged. By the time we went out, most places to eat were closed and she didn’t want to go to any bars or anything. She barely made an effort to engage in conversation and was just scrolling on her phone while we drove around. In the end, we decided to just call it a night.

Haunting Embarrassing Moments factsShutterstock

88. A Sly Twist Of Fate

This was the first woman I went on a date with after getting out of the army. She pretended to twist her ankle in the restroom as the bill came out. She then had me carry her, fireman style, outside to her car where she tried to convince me she couldn't drive because it put pressure on her foot (she was trying to get me to invite her back to my place, I assume).

When I asked her if any family members could pick her up, she said no. I was standing outside the driver's door at the time and she asked if I could just look inside to see if her foot looked normal. My naïve self just leaned in and that was a big mistake–she tried to kiss me. I pulled back saying I wasn't feeling that kind of connection.

She called me a terrible person, then burned out of the parking lot. She later proceeded to blow up my phone saying how sorry she was and that we were soulmates.

Lost Crush FactsShutterstock

89. Merry Christmas Rusty

The first red flag should’ve been his age—turned out, he’d fibbed about it on his dating profile and he was actually my dad’s age—but I vowed to muddle through. During our pre-date conversations, I’d mentioned I was into F1 racing and he said he’d attended the Canadian Grand Prix. He even brought an ancient photo album to prove it. That was the second red flag.

Before he got to the blurry Grand Prix photos, he flipped past yellowing boudoir photos of 1970s-era girlfriends and an ex-wife or two—think Farrah Fawcett hair, turquoise eyeshadow, and cheap, nylon babydoll negligees—and a Polaroid of a lovely Irish Setter. I said something like, “What a pretty dog". His reply made me squirm. “Yeah, I accidentally backed over him with my truck one Christmas morning". Merry Christmas kids, dad flattened Rusty. I finished my drink and went home.

Dark Secrets FactsShutterstock

90. Your Insecurities Are Showing

She wouldn't stop making fun of me. She was 26 and I was 36, but we were at the same place in our careers. Yet, she kept making ageist jokes about how I was old and decrepit. Eventually, after telling her pretty directly to lay off, I just said, "You know, I'm not enjoying this, I'm going to go". I then paid for the table and left.

Later on, she said she was acting that way because she was overcompensating for her failures. She said she felt self-conscious about how much younger she was, but to me, what she was really saying was that when she's uncomfortable, she goes straight to demeaning the other person. No thanks.

Toxic Partners factsShutterstock

91. Too Excited

On my first date with a guy from an internet dating site, he took me to the Scientology museum in London. I thought, "Hmm...That's original; plus, it's easy to find things to talk about, so it could be fun". Boy, was I wrong. He took the museum very seriously. He read every single piece of writing on every single exhibit and asked the attendant very probing questions about how one goes about joining Scientology. He sounded slightly too interested to just be intrigued about a religion. Also, he was visibly sweating.

Tom Cruise FactsShutterstock

92. Family First

I was on a first date with a friend in high school. After we went out for dinner, we went back to his house because he was hosting a bonfire. He introduced me to his father and stepmother, then took me to his balcony. The balcony was easily visible from their living room, which was where his family was. We were sitting on bar stools, chatting.

Suddenly, he stated, “I promised my dad I would always make sure to kiss the girl on the first date". That creeped me out, but not as much as his next move did. He pulled me from my chair and had me so that I was straddling him, and he proceeded to try to make out with me. I stopped his advances and called my friend to pick me up. It was so cringe-worthy because his parents were literally 20 feet away from the scene. We never talked again.

Wildest Things Found Inside Houses factsShutterstock

93. She’s Twenty-Four

I met a girl online. Everything seemed okay and the conversations were good, so a few days later we decided to meet for coffee and go for dinner later. I show up at the cafe about 45 minutes early and order a coffee, intending to read for a bit. While I'm reading, I notice an older fellow staring and taking far too much interest in me before leaving.

Odd, but okay. I continue to read until I text the girl that I'm already at the cafe. Shortly after, the odd older fellow comes back in one entrance, and this sets off my Spidey sense. I'm making my way to the other entrance when my date catches my arm to say hi. I tell her we should step out for a minute since I'm getting a bad vibe from this guy.

She asks which one, so I describe him. Her answer floored me. It's her dad, doing advanced recon for her dates...she was 24 years old. I was a bit sketched out at that, but thought maybe she had some bad dating history so that possibly made sense. I meet her dad, and he explains that they wanted to make sure I was who I said I was and to enjoy the date.

He leaves and she says being an only child has its downsides. Makes enough sense. We walk in a nearby park and decide where to go for dinner. We get to my car and she asks if I could take her home to grab a jacket before dinner, no big deal. We arrive at her place (she lives with her parents) and I talk to her mom and dad while the date grabs a jacket.

They seem like nice, but overbearing parents. Date calls me back to her room to meet her cat, and then it started to get very creepy. The entire time I'm meeting her cat, the parents are hawking nearby, obviously eavesdropping, and it's obvious the date is dragging her feet for some reason. I said something about getting out to dinner before the rush as I hadn’t made reservations.

Her parents, who "happened" to be walking by, ask where we were going before they start a monologue on local restaurants, which then pivots to ordering delivery/carryout and how we should just do dinner together at their place. I told them no offense, but I'd greatly prefer to dine in someplace relaxed and get to know their daughter.

They seem really resistant to this. I'm agitated and ask if this is how her dates normally go. They said, "no, normally we don't let her go out with men, but you passed the background check and your messages to her made you seem nice and like you'd have dinner with us". I was flabbergasted. They actually ran a background check on me.

They also read our texts, and expected me to have dinner with two additional people I hardly knew when I was expecting a date. I told them that will absolutely not work for me, and that they are being extremely over-the-top with their expectations and precautions. I left. Later, received a barrage of text messages and calls to the general sentiment of "you were supposed to be better than this".

Dating Horror Stories factsPexels

94. The First Cut Is The Deepest

It was the first date I'd ever been on. I wasn't the most talkative guy in school, but I rather fancied her so I worked up the courage to ask one day—and to my surprise, she said yes. We were both 15/16 years old at the time. I get a ride to her place from my mom, we pick her up and head over to this restaurant in one of the classier parts of town.

We get dropped off, head in, make light conversation and I find out she's never been there before. I'd only been there once myself for my birthday, a year or two ago. She asks me to order for her and I do so; two steaks with the trimmings. Anyway, things continue rather pleasantly and our food arrives. We dig in and continue to talk but I notice about 15 minutes in that she's gone a little cold on me and she hasn't yet touched her steak. She's picking off the veg and potatoes around the side, but the steak is untouched.

My natural reaction is that I didn't ask if she had any dietary restrictions; so, I apologize immediately and ask if she doesn't eat meat. Her response is so disturbing it’s unforgettable. She says she does eat meat, but: "I'm waiting for you to cut up my food for me!" Apparently, at the age of 15 years old, she'd never once had to eat a slab of meat that wasn't first cut up for her by either her parents or whomever else she was with at the time.

I was surprised, but I taught her how to cut up her own food—seriously, girl didn't seem like she'd ever held a blade before—and afterward, we dropped her off at her place in silence. So...thus ended my first date, and last date with her.

Floyd Mayweather Jr. factsPixabay

95. Outed!

Waited for her at the theater for two hours. She shows up plastered. Watched a terrible movie, just whatever was about to start. She took me to a bar afterward. Ended up being a gay bar and she tried to get me to admit I was gay. I flirted with the gay bartender to make the night less awful.

Animals’ Biggest Power Moves FactsShutterstock

96. Bad Suggestions

My twin brother passed in a car wreck and my family suggested that I should date his girlfriend because...grief, I guess? REAL FREAKIN' AWKWARD, MOM.

Worst Airplane Experience FactsShutterstock

97. The Worst Kind Of Deja Vu

A year and change ago, I had just gotten out of a bad relationship that I had broken off. I'm a driven person, and my work is what drives me. The relationship wasn't great, so I wasn't that torn up about having to end it. Several of my friends who don't know me that well assumed that I was super depressed, because I wasn't partying and going out as much as I normally do.

In reality, I just had a HUGE grant proposal to work on, which is a real pain in the butt and takes a lot of time. The relationship I had been in wasn't serious, and it was only for a month-ish "unofficially" so it really wasn't a big deal. She's a weird one, so I was in the middle of introducing her to my extended friend circle when things broke off.

My friends came up with this whole plan of meeting me somewhere and then not showing up, only to have me find out it was a blind date. So they did this, and called me right when I was outside the sushi joint to let me know. After getting angry, I figured what the heck, why not go in and share a meal with a stranger, what could happen, right?

Imagine my surprise...when the girl I had just broken up with was sitting there waiting for me.

Hate People FactsShutterstock

98. Stamp Of Disapproval

Years ago, I went on a first date with someone I met online. We met at a bar and the bartender carded us. Even though we were both older, they were still doing stings in the area, so he was carding every single person. I handed mine right over, but my date was a real jerk about it. The bartender checked mine and handed it back to me.

Then, he checked my date's ID, and rather than handing it back to him, he placed it on the bar right in front of me. When I saw it, my blood ran cold. It had the offender stamp on it, which is a thing in my state. The guy picked it up, looked at the bartender, looked at me, and then got up and walked out. I immediately Googled him.

He was on the registry and had been in prison. Lesson learned. Always Google. And that bartender? We’re still friends.

Dodged A BulletShutterstock

99. Musical Urinals

We went to a movie. During the movie, she got up to go to the bathroom. After she left, I thought I could run to the bathroom myself, and be back before her (for some reason, I thought it would be rude to leave her alone). When I came back to our seats, she was already there but I didn't give it much thought.

I hung out at her place for a bit afterward, gave her a kiss goodnight, and went home thinking that I just had a pretty nice date. A week later, after she wouldn't return any of my calls, I asked our mutual friend who introduced us what the deal was. Turns out that when I went to the bathroom, I accidentally walked into the women's room.

I peed in the stall next to her, and she recognized the boots I was wearing. She was totally freaked out. When I finally got a hold of her and tried to explain myself, she told me she was moving to Turkey to get back together with her ex-boyfriend.

Worst Thing Done on a Date FactsMax Pixel

100. Oh, Those Summer Nights

A couple of years ago I went on a date with this girl who I had a crush on in my college math class. I was too scared to ask her out and didn’t do so until one summer day when she hit me up on Snapchat asking about some tea places that I knew of. I told her some places, then I shot my shot, saying we should check one out together.

She agreed. I picked her up and we went to the tea place. We had a really nice time and even played Jenga. I didn’t want the date to end, so I took her to a lighthouse on the beach. We got to know each other so well and had nothing but a great time laughing the night away. Night eventually came and she had to go home, but we planned on hanging out again soon.

A week or two later, I woke up and checked my Instagram. The first post I saw made my blood run cold. It was her with another dude at the same beach holding on to each other. Mind you, she told me she was single and not talking to anyone. I was heartbroken even though we only hung out that one time.

Strangest things done online factsShutterstock

101. A Relaxing Vacation

I met this guy. We vibed right away and started hooking up within a day or two. This guy swept me off my feet and I couldn't help but think, “Yes! FINALLY, a real man". Then, one day he said to me: “I know this house we could go stay at for the weekend if you’re interested". Sounds great, right? But then we got there and he said he forgot his he proceeded to get a crowbar.

That freaked me out, so I asked him to explain exactly whose house we were at. He assured me that it was his dad’s summer house and he definitely had permission to use it. I ignored my gut instinct and decided I was probably just freaking out for nothing and overreacting. We stayed there for about four days, with no more issues.

I slept in the master bedroom, showered there, made food in the kitchen, the works. When we left, this guy said, “Look what I got".  He proceeded to show me jewelry and some credit cards from the house. I was starting to truly panic now. As naïve as I was, I still thought it was his dad’s house and he was just having a rebellious moment.

And that’s when he fessed up. I realized that I’d just helped him burglarize this home. It wasn't even his dad's house; it was his mom's ex-boyfriend’s house, and let me tell you—they did NOT give him permission to be there. His stepdad even had a restraining order on him for a similar incident a few years before.

So fast forward a few weeks—I got pulled over and snatched out of my car for having been involved in this whole thing because these people had rightfully pressed charges. I ended up narrowly avoiding doing serious time.

Creepy Moments FactsShutterstock

35. I’m Gonna Getcha

I was dating this girl who asked me to go to her ex’s wedding. We dated for a few months prior, but asking me to go to a wedding together felt like a serious commitment...I still accepted. I planned for the week off work and we went all out for this wedding. Half the time, I was trying to make the most of our time together, but she always went missing.

Fast forward to the reception. She made a scene in the most unstable and mentally sick way. In front of the groom, the bride, and everyone else, she said out loud: “I’m still in love with you. We literally have been sleeping together all week and I can't stop thinking about you". She quickly got escorted out after that.

The bride was clearly upset, but everyone tried to go about their business. As soon as I left, my “girlfriend” started completely ruining the hall and all the decorations, just throwing a fit on her way out. It was so embarrassing. I figured she was telling the truth since she was missing the whole time, but I’m pretty sure that everyone during the whole thing assumed this was too crazy to be real.

I definitely regret not seeing her true colors before, but when you work so much and try to date at the same time, you have very little time to get to really know some people. Time sort of flies by and you end up dating for a few months. Fast forward a month or two later...she got together with the groom and I’m pretty sure she has no regrets about wasting my time.

She probably doesn’t even feel bad about using me or even ruining that man’s marriage. This woman is seriously twisted.

Weddings Gone WildShutterstock

50. No Regrets

A girl who was a good friend of mine in high school once shot me down and wanted to stay friends. She then started dating my buddy. I thought, cool, no problem, because she would set me up with her friends, and I had a lot of fun. I didn’t ever find a girlfriend in high school, but I still had a blast, if you know what I mean. We graduated, went our separate ways, and grew apart while in college.

I got a girlfriend, and I ended up marrying her after college. But not long after I married my wife, my old friend started calling me. At this point, she had been married for several years to someone I didn’t know. We started talking like we were friends again. She told me she was pregnant, to which I responded with, “Congratulations! Excellent! Good for you guys!” Strangely, she told me before she told her husband.

She later found out she was having twins, and a few days after, she told me she had crazy regrets. I asked, “Oh yeah, what’s that?” She answered that she regretted that we never got together. I said, “That was because you turned me down and dated my buddy. We were friends.” She then responded that just this once, we should hook up now. I immediately turned her down, but she was adamant that we could.

She reasoned that because she was already pregnant, we had no worries there. But I declined her offer again. That’s when she said something truly messed up. She said she wished her twins were mine and hers and that she’d been in love with me since the very beginning. She also told me that she always thought we would end up together until I started dating someone seriously. Flabbergasted, I replied, “Sorry, we need to stop talking.”

I think she was having marriage problems and wanted out. She knew I once liked her years earlier, so instead of just ending her marriage like an adult, she was looking for another excuse to blow it up. She also knew I’d graduated college and landed a job in my field; she tried to blow up her marriage with a blue-collar guy. I quickly noped out and told her we couldn’t be friends and that she should really fix her marriage.

I lost her number and never looked back. I lived a long way away, so she couldn’t just show up. I did tell my wife immediately after the conversation happened. She thought it was funny. She even kept this old friend on Facebook.

Creepy womenUnsplash


Sources: Reddit, , , , , , , , 9, 10, 11, 12, 13, 14

More from Factinate

Featured Article

My mom never told me how her best friend died. Years later, I was using her phone when I made an utterly chilling discovery.

Dark Family Secrets

Dark Family Secrets Exposed

Nothing stays hidden forever—and these dark family secrets are proof that when the truth comes out, it can range from devastating to utterly chilling.
April 8, 2020 Samantha Henman

Featured Article

Madame de Pompadour was the alluring chief mistress of King Louis XV, but few people know her dark history—or the chilling secret shared by her and Louis.

Madame de Pompadour Facts

Entrancing Facts About Madame de Pompadour, France's Most Powerful Mistress

Madame de Pompadour was the alluring chief mistress of King Louis XV, but few people know her dark history—or the chilling secret shared by her and Louis.
December 7, 2018 Kyle Climans

More from Factinate

Featured Article

I tried to get my ex-wife served with divorce papers. I knew that she was going to take it badly, but I had no idea about the insane lengths she would go to just to get revenge and mess with my life.

These People Got Genius Revenges

When someone really pushes our buttons, we'd like to think that we'd hold our head high and turn the other cheek, but revenge is so, so sweet.
April 22, 2020 Scott Mazza

Featured Article

Catherine of Aragon is now infamous as King Henry VIII’s rejected queen—but few people know her even darker history.

Catherine of Aragon Facts

Tragic Facts About Catherine of Aragon, Henry VIII’s First Wife

Catherine of Aragon is now infamous as King Henry VIII’s rejected queen—but very few people know her even darker history.
June 7, 2018 Christine Tran

Dear reader,

Want to tell us to write facts on a topic? We’re always looking for your input! Please reach out to us to let us know what you’re interested in reading. Your suggestions can be as general or specific as you like, from “Life” to “Compact Cars and Trucks” to “A Subspecies of Capybara Called Hydrochoerus Isthmius.” We’ll get our writers on it because we want to create articles on the topics you’re interested in. Please submit feedback to Thanks for your time!

Do you question the accuracy of a fact you just read? At Factinate, we’re dedicated to getting things right. Our credibility is the turbo-charged engine of our success. We want our readers to trust us. Our editors are instructed to fact check thoroughly, including finding at least three references for each fact. However, despite our best efforts, we sometimes miss the mark. When we do, we depend on our loyal, helpful readers to point out how we can do better. Please let us know if a fact we’ve published is inaccurate (or even if you just suspect it’s inaccurate) by reaching out to us at Thanks for your help!

Warmest regards,

The Factinate team

Want to learn something new every day?

Join thousands of others and start your morning with our Fact Of The Day newsletter.

Thank you!

Error, please try again.