For all those in search of true love, here are some cautionary tales. Dating, for the most part, is pain, pain, and more pain—but these Redditors truly managed to find the worst possible dates on the planet. From creepy slimeballs to oversharing weirdos, these dating disasters might just convince you that singledom is a downright paradise.
1. Everyone Loves A Good Nap
She looked great when I picked her up from her house. The first thing she asked was to go to the convenience store, where I bought her a big box of discount tampons and two packs of smokes. She opened the smokes and lit one up and then opened the tampons and installed one right there in the front seat. She crumpled up the paper and tossed it on the ground.
I started to drive to the restaurant. During the drive at some point, she fell asleep. We got to the restaurant and I couldn’t wake her up. The more I tried, the nastier she got. I drove her back home. Then spent about 25 minutes trying to get her up and out of the car. She called me the next day and apologized. She told me she took a Xanax right before I got there.
She also said it was good I brought her back early because she was supposed to be babysitting her sister’s kids. Her sister came home early and I saved her from a bunch of problems. Although we talked on the phone, we never went out after that, and I quickly lost track of her after. And I have absolutely no idea where she is today.
2. Anything But A “Happy” Hour
I met a guy at a concert who asked me out to dinner the next weekend. He gives me the address, but I get there and it’s an apartment building. I call him to say I think he gave me the wrong address and he said, “Nope! You’re driving.” He has me take us to an Applebee’s because they have the cheapest happy hour. This is exactly what he said.
We have one drink and he eats potato wedges by himself. When I drove him back, he asked me where my overnight bag was. I said, “I’m not staying the night, and thanks for the beverage.” He turned savage in an instant. He took my keys out of my ignition and told me to go upstairs. I told him I will start screaming and call the authorities, which was the only thing that made him back down.
He threw the keys in the front seat as he got out, telling me I was missing out on “hot tub time.”
3. If She’s That Great, You Date Her
She was nothing like her profile picture and just a horrible person. But it was after the date that it got truly….”interesting.” She stalked me to my van and took down my phone number. On the way home, she asked if I would come back and see her. I said thanks but no thanks and have a nice life. In the proceeding days, I received numerous texts and phone calls from her and had to have her number blocked by my phone provider. Oh, that was not the end.
On New Year’s Day at 4 am, I receive a call…from her ex-husband, asking why I wouldn’t date her. He tells me that she’s a good person and all that. Turns out they went out on NYE and decided to call me. I hung up only for them to keep calling me back. Ended up turning my phone off. When I turned my phone back on, I had received 20+ voice recordings that were getting more and more threatening.
In the last one, I could hear them in a car saying they were coming over to get me. I spoke to my neighbor who gets up early and had gone for a run and he told me there was a couple being taken into custody around the corner from our place who had hit a light pole.
After a movie date with a guy I met on Tinder, we went back to my place. I told him we could hang for a bit but I have work in the morning so I would need to go to sleep soon. Dude said that was fine, but he was hungry and he was going to order food. Ok sure. Dude orders 2 large subs from PotBelly and a milkshake. Downs it. No judgment, he’s 6’4, 210 lbs., younger still growing, by all means. I didn’t think anything of it until later.
We end up messing around a bit and fall asleep in bed. I wake up to my front door opening and closing several times over a 5-minute period. My dogs are going nuts, and it’s 1 AM. What the heck is this guy doing? I open the door to my room that opens up to the rest of my apartment and my bathroom is to the left where the light is on and the door is wide open, I walk around the corner—and almost puke. I instantly make eye contact with Dude who is in a squatting position over my toilet, with a stick, poking around in murky brown poop water that is millimeters from overflowing onto my bathroom floor.
Horrified, he yells, “Stop looking at me! Go back to bed! I have it under control!” I’m still waking up trying to understand what I’m seeing and what’s going on, and I just start nervous laughing I don’t know what else to do. He yells, “Why don’t you have a plunger?!?” And I said I don’t know I never needed one until now!! He tells me to go back to bed he has it under control, I’m so disturbed, tired, can’t process what’s happening and have work in the morning I go back to bed. I remember hearing him peek in my room a bit later and heard, “I fixed it,” and then heard him leave and my door close behind him.
The next morning. I hesitantly approach my toilet to find the water is down. But there is something poking out from the bottom of the toilet like he didn’t get it all. Upon further inspection, what I was seeing was the tip of a stick. Some gloves, towels and BBQ tongues later I pulled out approximately 3 foot of stick from my toilet that had broken off, followed by several other stick fragments.
Dude had broken several sticks. I heard my door open and close so much because he was going outside to look for a stick, one would break, he’d go get another. Dude had left drippy poop water stains all over my bathroom floor. He also left my apartment so fast that he left his underwear, and undershirt and socks. After work that day, I went straight to the store and bought a plunger. Lesson learned.
5. Petty Theft
When I worked as a bartender for a while, this one girl who was a regular came in and told me about an awful Tinder date she had. Not sure of the specifics, but it wasn’t bad enough for her to not bring him home afterward. He leaves the next morning, she brushes it off as a one-night stand, and a few days later, her debit card gets declined.
Odd, since she is a bartender herself at a fairly busy place in our city and is good about saving and usually flush with cash. She goes to check her debit card and it turns out there were a bunch of charges at Best Buy, Grubhub, a bunch of other stuff. Curious, she checks her credit card too. There she found a bunch of charges for streaming services—Netflix, Hulu, everything.
She goes to confront the guy and finds out he deleted his profile. But she remembers a friend they had in common on Facebook. She reaches out to the mutual friend to try and track him down and it turns out he did the exact same thing to that mutual friend. I’m not sure of the outcome, but she was out for blood after a mediocre hookup turned into a serious case of identity theft.
6. 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.
7. Talk About An Icy Encounter
In college, I hit it off with a girl and agreed to go on a first date to a school hockey game. When I met her there, I realized I had forgotten my wallet, so I had to borrow $5 from her to pay for my ticket. Not a great start, and I could tell I had dug myself an early hole. Then, once we sat down, we realized that neither of us liked hockey at all.
I have no idea why we agreed to meet there, but we were both totally uninterested in the game. We started talking about other things we were into, and I mentioned that I liked board games. She said, “You sound like my grandma.” At that point, it was clear that neither of us was into this at all, but it was the first period of a hockey game that she had paid 10 whole dollars for.
We sat there and stonily watched the rest of the game. Afterward, we said, “Let’s hang out sometime,” and then never messaged each other again. Here comes the twist. A few semesters later, my friend called me up all excited about a new girl he was dating. He wanted me to come to his apartment and meet her. I walk in, and he’s sitting on the couch with his arm around the very same hockey-hating girl.
I immediately grabbed my wallet, handed her $5, and said, “Thank God! I’ve been looking for you for two years!” She laughed, and things went all right after that.
8. Hollywood Escape
On OkCupid, summer 2006, I met a girl in West Hollywood and we went to dinner. She turned out to be way bigger than her pictures, insanely rich, was Ozzie Osborn’s cardiologist’s daughter or something like that, and had a bad substance habit. The whole date she was doing stuff in the bathroom and barely ate her food. Then afterward, we went back to her place where she visibly spiked my drink with a mickey.
Then she asked me to tie her up, and then refused to allow me to drive my car out of her garage, leaving me to wait in my car all night until the morning when I followed someone out. She called three days later to say that I caused her miscarriage. I did not know she was pregnant.
9. 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 make-up. 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.
10. Up in Palms
I made the mistake of taking this girl out around my friends. She started reading palms and telling everyone they were going to have miscarriages and abortions. Everyone.
11. The Architect Should Be Fired
A guy approached me at a coffee shop and we ended up hitting it off and talking all night. A week later, we had our first date at my place so I could cook him dinner. I lived in a small one-bedroom apartment and the bathroom door was right next to the kitchen. He excused himself and proceeded to take the loudest, and what I presumed to be, the most massive BM this universe has ever seen.
The sounds of the toilet carnage still echo in my nightmares. I didn’t mention that I heard the whole event and we went about our evening. After dinner, we got into my bed so we could watch a movie. 30 minutes into it, I needed to use the restroom, so I got out of the bed…to reveal that I had unknowingly started my period and left a noticeable pool of blood where I was sitting.
He helped me change the sheets. Anyway, we’ve been married a year now and he still takes the nastiest dumps known to mankind.
12. Hands to Yourself
This woman seemed really cool. We were both 25, she’d just finished her masters, and was job hunting. She was fit, witty, and had piercings. I was a fan. We meet. Well, fit was apparently five years prior, but there was a 70-85 lb. difference from photo to reality and she was “trying to get back to her normal weight” and so thought it appropriate to use the older photos.
I’m a pretty fit guy and have always been fairly health conscious so this doesn’t appeal to me, but we can be friends. She’s witty though, so we talk. Where’s the wit? I toss her a couple of verbal jousts. Nothing. It turns out her roommate had been helping her reply to messages. That’s cool, I can be friends with nice people who aren’t witty.
Okay, well her nose ring is actually a weirdly shiny wart that she tries to pass off as a nose ring because she’s embarrassed by it. All of this isn’t the worst part though. We were out for dinner and went to a decent gourmet pizza joint with low lights, thin crusts, and wine. Without asking, she reaches over and starts picking toppings of my pizza. Pardon me, but keep your hands off my prosciutto! It was unforgivable.
13. 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.
14. Stay Home Next Time
We went out to a nice cafe and she made the barista remake her triple shot latte multiple times while hovering over the coffee machine and criticizing their milk frothing and bean grinding and shot extraction and milk brands. Then she asked to come behind the counter and do it herself. She was the coffee girl at a gas station so she thought she knew better.
She even complained about all the awful customers she had to deal with…while she was eyeballing the person remaking her coffee for the third time!
15. You Had One Job
I went to the bathroom and asked my date to watch my coat. I came back and my coat was gone. It had my cellphone, wallet, and keys in it. Turns out, the guy was too busy chatting up the bartender and hadn’t even seen what happened. We had to uber back to his house so he could get his truck and drive me home. I had to wake my roommates up to let me in.
I had no ID, cash, or way of contacting anyone for days. I ended up tracking down the guy who took it but only got back my phone; he threw out my wallet, keys, and coat. Most expensive and worst first date ever!
16. 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.”
17. Worst First Kiss
I went on a date with a handsome, smart, funny guy who was getting his PhD in mechanical engineering. We had a fantastic time though he did get a little awkward with his humor at times. Normally I don’t kiss on the first date, but I had such a nice time, so when he walked me back to my car and went in for the kiss, I reciprocated. Holy. Ouch. Terrible.
I couldn’t get away. I made up some lame excuse, “I gotta go let the dog out,” and left. The next morning, I woke up with a bruised lip. Five days later, I went to the ER, sicker than I’d ever been. It Turned out I had mono AND strep throat. I wrote him a text apologizing saying that he might want to go to the doctor…his response? “LOL. I had that.” He gave it to me.
18. 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, 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.
19. Some People Aren’t Worth The Fuss
I started a new job, and met this super cute guy at work. He had a previous girlfriend who he broke up with about six months before we met. She would sometimes randomly come into the shop, and he would always tell her that she couldn’t be there, that they had been broken up for months, and she needed to leave him alone. Anyway, he and I started talking and flirted for several months.
After about three months, he finally asked me on a date. We go out to dinner, and he’s just so sweet and cute and adorably awkward; I really liked him. After dinner, he invited me back to his place to talk. I agreed, and we just chilled at his apartment talking, and talking. I was sitting on one sofa and he was sitting on the other. Then my nightmare began.
All of a sudden, there was pounding on his door. He calmly gets up and locks it, and I hear a female yell, “Did you just lock the door on me?!” It was the ex. He’s calmly asking her to please leave through the door. Then the front window slides open, and she sticks her head in and starts screaming at him. At this point, he’s still calmly asking her to leave.
She then CLIMBS IN THROUGH THE WINDOW and I see this HUGE woman and I thought I was about to get hit. She went ballistic and started tearing down pictures in the living room. Then she moved to the bedroom and I could hear her screaming, throwing things, breaking stuff, all the while my date was standing in the doorway of his room trying to get her to stop.
He never raised his voice, and it seemed like this wasn’t the first time this happened. The neighbor came over, but she didn’t do anything except stand next to me in the front doorway in shock. Meanwhile, we can hear things escalating with her in the bedroom. He calmly walks in the bedroom, and after a minute or so he walks out of the bedroom with her in a bear hug, guiding her out of his house. It was far from over at this point.
She then went and laid down in the courtyard, rolling around in the grass, crying and screaming, while the three of us (me, date, neighbor) just stood there for a minute. My date then said he was going to call her cousin to come get her, but before he could make the call, the cousin walked up. The cousin brought the girl there and was waiting in the car the whole time!
I sat with my date and we kind of processed what just happened, which is when his neighbor confirmed for me that this is not the first time, and I encouraged him to call the authorities. I eventually left and called him when I got home to see if he called the police. He did, but not to report what happened, but so they would do a welfare check on her to make sure she was okay.
20. Punning Photos
My dad had been on Match.com for about three months with some success as he’s a tall Australian man who’s decent looking so he had some interest. One weekend he got sent his first “sexy pic” which he thought had strange, but brushed it off. Later that week he got six more pictures from the same woman. Before he blocked her, he decided that he would open them just for kicks.
Five of the pictures are just straight up coochie shots, which he said were incredibly unappealing and had terrible lighting. The sixth picture however was something different. The woman was standing in her bra in front of a mirror, no bottoms, winking, with a bunch of herbs shoved in her bra. Basil, parsley, thyme, all that good stuff. The caption on the picture was “spice rack.” She was swiftly blocked after my dad stopped laughing long enough to find the block button.
21. 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.
22. Pure Confusion
I took a girl out for the first date for dinner, and she showed up in a dirty T-shirt. She ordered a lot of food and ate open-mouthed. She then starts talking about her fiancé, her child that she did not know who the daddy was, and then, she farted. Like she leaned over and pushed one out. Just as I thought it was bad enough, she then asked me if I had any blow.
When I said no, she asked if I knew where to score some. She then told me she had to be careful because she was out on parole. There. Was. No. Second. Date.
23. Really Nosey
I went on a date after talking to this guy for a few weeks and I told him I was thinking of getting my nose pierced but was afraid it would hurt. We are walking through a park in broad daylight and this dude takes a safety pin out of his pocket and jams it through his nostril. Blood pours down his face. He laughs and says, “See? No big deal.”
24. A Steep Climb
I matched with a cute girl who likes to go climbing and we have good chat. I suggested we go to a climbing gym rope and hang out. But she doesn’t have a car, so I need to pick her up. I’m not thrilled but whatever. I meet her and, well, it’s not her. Or it is her from the profile, but maybe from 5-8 years and a kid ago? Something like that.
I’m tempted to call it off but I’m too much of a softie, and she says she made cookies. As it happens, I love cookies. We head off to the small local gym. We arrive, walk the 10-minute approach, and the conversation is still fine but I’m really wary now. I resolve to just have a nice time and have some fun, and just learn from the experience.
She’s perfectly nice but I’m seeing red flags. At the crag, she says she borrowed her friend’s shoes and isn’t sure they’ll fit. Same with the harness. Uh oh. Well, they do fit, so I rig the anchor and we start climbing on a nice easy wall for a warm-up. Except that she can’t climb. Fine, okay, whatever. We’re still chatting as she works on the off-ground move, and then just bursts into tears. Then the whole shocking truth comes out.
Turns out that it’s HER SISTER’S DATING PROFILE and that’s who she borrowed the stuff from, and that HER HUSBAND DOESN’T KNOW SHE’S ON DATING APPS. I find all of this out amid tears and so does everyone else there who can overhear it. Some very awkward talk therapy later, I drop her back at her house and she leaves me the cookies as an apology. And they were store-bought.
25. Blame It on the Mai Tai
I went on a Tinder date a couple months ago on a Sunday afternoon. I met up with the guy around 3, he had a really good energy and was funny and complimentary. The place we wanted to go had a long line, so we went to another restaurant on the water for a drink and appetizers. He started slamming down Mai Tais. I had one, he had 3. They were STRONG. Like, I was tipsy borderline drunk off of one. The bar had a 2 Mai Tai per person limit, but he found another bartender to get his 3rd.
He got drunker and drunker and started telling me he loved me, joking at first but getting increasingly serious. As we left, he asked me to marry him, I kind of laughed it off, and was like “maybe we take it slow, we just met each other.” He got so mad he stormed off and left me on a street corner. Then as soon as he got home around 5 PM, he started texting me “come over.” And “I miss you.” He was 43.
26. Parents Have Friends Too
I was set up by a friend’s girlfriend. She showed me a picture and said sure. The girl was good-looking and I liked the girl’s other friends that I had met. She couldn’t be too bad, right? I call her and set up the day and time for pickup at her house. I arrive to pick her up and there she is with her parents and brother sitting around the kitchen table just talking.
I get a bad vibe from everyone but her when she introduces me. On the way to dinner, I mention the tension I felt from them all. She says it’s because she just broke up with her boyfriend a few weeks before. Her family loved him and they were all upset with her dating someone else. She said maybe they’ll get over it and like me once they get to know me.
Later on, I ask about her brother. No brothers. OK, cousin? No boy cousins that she is close to. So…what about the guy with her parents when I picked her up? That was her ex. There to have dinner with her parents.
27. Please Do Not Touch
I met a guy, chatted, and he seemed relatively normal. We go for our first date in a pub, a well-lit pub. We’re having a couple drinks, talking and whatnot, I see his hands under the table, moving around. It cannot be. OH. BUT IT IS. He was touching himself. Apparently, I was turning him on too much and he couldn’t help himself. The date ended pretty quickly after that.
The follow-up is when I got home, he’d sent me an epically long email about how I was fat and ugly and a tease and even worse things. Oh, and ended it with the phrase, “Don’t bother responding, because I will not read it.” Done and done!
28. In Her Defense, It Was Dark
I had a dinner date with a much younger woman who was extremely aggressive. After our first date, I was dropping her off and had intended only to give her a thank-you peck on the cheek. However, our “goodbye” moment suddenly morphed into a high school-like make-out session during which she started, shockingly, to grope me.
My two-seater car was dark and cramped and I was wearing a suit and winter overcoat, but I nevertheless was extremely surprised to feel her hand navigating south of my belt. Suddenly she squeezed hard and, with sheer delight and fire in her dimly lit eyes, delightedly exclaimed that I had “an enormous friend.” But she didn’t know what she was actually touching.
In reality, she was squeezing a single large roll of my lower belly! For the first and last time in my life, I glanced at my pretend wristwatch and told her that I had to leave due to the late hour and an early morning meeting. I couldn’t imagine her reaction and disappointment had our date developed any further as I am, at best, average.
29. Following up in Person
We were supposed to meet at 9 PM. He fell asleep and called me at 9:30 when I was already at the carnival. I told him not to bother coming as I didn’t want to see him. He asked for another chance and I agreed. Unfortunately, my dad got really ill and had to spend the next six weeks in the hospital with me visiting him daily. I had no time for dates and he got extremely mad.
He made a fake Instagram account which he used to follow me and everybody that I followed. He then saw me in a friend’s Instagram story and showed up to the restaurant we were at. He called me a liar and we had to threaten to call the police because he would not leave.
30. Open And Honest Isn’t Always Best
I met a girl at a friend’s wedding and we went on a date a month later. She started disclosing way too much info for a first date, including some very personal stuff. She said that she wanted the first time we kissed to be on the altar when we would get married. I’m not religious by any stretch of the imagination.
Then we went back to my place and through five walls, I heard her perform what can only be described as a three-ring circus of bowel movements. A month later she invited me to a Halloween party and said she was dressing up as a sexy Bruce Willis. HARD PASS.
31. Kratomic Projectile
I went on a first date with a girl from Tinder at a Cajun restaurant in Dallas. I had read recently about some stuff called Kratom that is supposed to make you feel really relaxed and euphoric, and I had tried to make a tea from the recommended dosage the previous day, but I didn’t feel anything off of it. So, I figured if this stuff was supposed to make you be cool and euphoric then the best time to take it would be for a first date and since I didn’t feel anything from it the first time, I figured I should take more.
I wrapped a LOT of it up inside of balls of deli meat and swallowed those whole before the date. I then went to the lunch feeling nothing until I met the girl and sat down when I suddenly realized that something was seriously, seriously wrong. I came to the realization that I was a few seconds away from projectile vomiting up all that Kratom and deli meat in the middle the restaurant. I excused myself, got up from the table, made it a few steps towards the bathroom…and began to violently vomit.
At this point, I covered my mouth with my hands, began choking on my own vomit as I sprinted towards the bathroom, leaked a trail of vomit all over the floor in a path towards the bathroom, then continued to violently projectile vomit into the trash can in the bathroom. I then spent a while to clean my face and wash my arms and hands which were soaked in vomit. I then returned to the table and tried to survive the rest of the lunch date without dying of embarrassment. I felt like a huge jerk and was really embarrassed.
32. So Uncomfortable
A person I was dating invited me to his parents’ house for the afternoon. He wanted to introduce me to them and show me the house he grew up in. I thought it was super sweet and had no problems going. He was also in the middle of moving and needed to pick up a few things, so it really didn’t seem that unusual to me. Yeah…we got there and it was awful.
His entire family was there. They traveled from hours away, too. This was not just meeting the parents, it was meeting the ENTIRE family. Even worse? At some point, this lunatic lied and told his parents that he had proposed. We had been dating TWO months. I spent the entire afternoon dumbfounded and just playing along.
We were two hours from home and I had no cell service, and no way to leave at all. We ended up spending the afternoon brainstorming wedding ideas and planning an Alaskan honeymoon that his parents planned to gift us. His brother even called to say congratulations! We drove back to his apartment in silence. When we got there, I got in my car and left.
I didn’t even bother grabbing my stuff. Weirdest experience ever. I have no idea how he broke it to his parents that we weren’t getting married
33. Wetting the Bed
I met this girl on Tinder and went for a lunch date. We had a pretty good connection so we decided to have dinner as well. After having a few drinks, one thing led to another and we ended up back at my place. We hooked up and went to sleep. Middle the night I wake up. She’s intensely staring at me while she’s crouched behind the bed. I asked her if everything is alright, she said yes and got back into bed…I thought “little creepy, but probably nothing to worry about.” I was so wrong.
She lays down to cuddle with me and she’s wet. At the time, I was like “dang I must just be a stallion.” Fast forward to the morning, she’s gone and there’s a wet puddle beside the bed. She peed on my floor. I still don’t understand it. I had a bathroom, but maybe she just got lost and couldn’t hold it? I did not hear from her again.
34. An Odd Thing To Do
I went over to a boy’s apartment who I had hung out with a few times already to watch a movie. In the middle of the movie, he stuck his finger in my belly button. We weren’t even cuddling. Just randomly turns towards me and puts his finger in my belly button. I said to him, “Get your finger out of my belly button?” To which he responded by making a weird noise similar to an adult using baby talk and saying, “Coo, coo,” while wiggling his finger still inside my belly button.
I left immediately, never talked to him again, and my friends still refer to the situation as belly button boy.
35. Just Like Mom
I talked to this guy for two weeks before we went out and no red flags so we ended up going out to dinner. I said I hadn’t been out in a while because I was trying to save money for a washer and dryer. He told me instead of saving for that I should save for a boob job. I didn’t even know how to reply so he followed up with, “No it’s not a bad thing, my sister and Mom both small chested and got boob jobs and they look amazing.”
This is all before the waitress even brought our drinks. I just got up and left.
36. He Was Not Trying At All
We went to dinner and he started chatting up the waitress. He was interrupting me every time the waitress came over and talking to her for a few minutes instead. After a couple of times, I just pulled my phone out and started scrolling and he complained when he noticed I was on my phone. Cue a lecture about my generation.
He was only six years older than me. Then he got mad when I wouldn’t get intimate in the parking lot. I ended up going back inside the restaurant and calling a friend to pick me up. Dude’s car was still sitting there when I left. Maybe he went back for the waitress.
37. Night Out
This happened right as I decided to get into the dating scene after a traumatic end to a three-year relationship. It’s 12:45 AM and a Tinder match messages me asking what I’m doing, then invites me to go out with her. I think it’s a bit late, but the clubs are open for 3-4 more hours so why not? I should take opportunities, right? I’m a single man in his 20s for the first time.
She says she’ll pick me up and I put on cologne and a nice shirt, get ready to go out. I go to the car. My match is in the front passenger seat and her friend is driving. I think it’s pretty weird but having a friend along isn’t super off so I get in and ask which club we’re going to. “We’re not going out-out, just out.” My match says as we drive off. “Where are we going?” I ask, feeling a little uncomfortable. “Just into town,” she replies. I got a terrible feeling in my gut, but it was too late.
They drive to a nearby bridge with a carpark under it and park, turn the radio up and start chatting. The Girl driving pulls out a 1L bottle of chocolate milk and starts drinking it, everything they talk about is boring and they barely include me in conversation and start rolling cigarettes. After 15 minutes they get out of the car to have a smoke, I get out too.
My Tinder match is wearing fluffy white slippers that light up with each step. I turn and face them, “I appreciate you guys picking me up but this really isn’t my scene, I’m going to head off, have a nice night.” They were very offended.
38. 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. Until later on when she told me, “I don’t believe in outer space,” and my head freaking exploded.
39. Chance McMeeting
This girl I matched with just messaged to mess with me. I was like, “Hey what’s up” and she was like “Don’t talk to me unless you plan on doing me.” I forgot what my reply was but she obviously never messaged back. Then a week later I’m getting McDonald’s and this girl was the one who handed me my food. She recognizes me instantly and just had this total look of fear in her eyes.
I walked out of there so quick. That poor girl thought I purposely sought her out to confront her or something.
40. What Friends Are For
I was 21 and met a guy at my summer job who was 20. He was a super sweet guy and we got along great when we worked the same shifts together. Eventually he asked me out on a date Saturday night, and I said sure. He said we would go out to dinner, hang out around town, etc. I was really excited because he seemed like a great guy and I never went on many dates.
I pull up to his house and he comes out with three other guys. They all jump in my car and I’m like, “Oh, hello?” And they said they wanted to have a party that night and started directing me around to all the local liquor stores so I could buy things for them. I was a shy, self-conscious girl with low self-esteem and I was always a people pleaser who didn’t stand up for myself, so I obliged.
I drove these little dinks around town, picking up drinks for them while they sat in the car, feeling like a complete and utter idiot the whole time. But the worst was yet to come. When we got back to my “friend’s” house and I parked and started taking off my seatbelt, they started laughing at me. “Who said you were invited?” I was totally non-confrontational so I just said, okay, see you later.
They hopped out of my car, took the drinks with them, and I drove home, totally burning in embarrassment. Once I got home, I told my roommate what had happened. She was enraged and immediately got them busted for underage drinking.
41. Foot Problems
I went to his place and we hooked up, but after he goes “So you wanna know what I’m really into?” And I was like sure and then he grabs my foot. I have a really irrational fear of people touching my feet so I ran the heck out of there. Anyway I get to the living room on the way out and it turns out to be his parent’s house and I look at his mother and see she was my old therapist.
42. A Big “No Thanks”
After a couple of rounds of drinks, my date started crying and it got visibly worse throughout the night. It was clear she was not over her ex and especially not ready to be in the dating scene. She excused herself for 20 minutes to the restroom and came back looking somewhat better, but a couple of moments later it all started again. I was just awkwardly sitting there and was getting stares from people.
I eventually ended the night, told her to go home and rest, and that it was all ok. She apologized and even texted me the next day asking for a redo but I politely refused and wished her well. I thought that was kind, but her reaction stunned me. She then had audacity to be upset about that and texted me a whole rant. I didn’t even bother responding.
43. No Biting
I met a guy, decent conversation, smart, funny, mutual nerdy hobbies. We decide to meet up at the local gamer bar and play some games while having our first date. Get in, sit down, dude has no teeth. He says a hack dentist told him they all had to be removed, couldn’t get dentures due to budget, needed to wait for bone shards go fall out of his gums, etc.
He proceeded to spit all over our food while talking, which granted, I knew he couldn’t help, but if he can hide something this big from someone, what else could he be hiding? Plus, I couldn’t stomach the thought of making out with someone with no teeth.
44. All Mucked Up
Well I’ve only gone on one Tinder date, we talked for a bit and I agreed to pick her up at Starbucks. She looked nothing like her pictures, but I thought I should be nice and at least hang out with her for a bit. We went to her place and the entire house reeked like cat pee. Like saturated. Then as she proceeded to show me her massive collection of insane adult toys, she screamed at her chihuahua and smacked it right on the nose and without missing a beat just asks if I want to make out on the couch.
I awkwardly sat down and pretended to look at my phone and made up that my grandma was dying so I could leave.
45. What A Winner
I showed up to a date with a guy who looked nothing like his pictures. I don’t know if they were really good angles or super old. He was also covered in tattoos that looked like a kid had drawn them on and was very proudly showing them off by wearing a string vest. Whatever, I thought, I’m not superficial, so I decide to give him a chance.
He proceeds to begin the date by telling me he lied. He doesn’t have a job; he collects unemployment and he saved some especially for this date. No judgment on being unemployed, but a pretty big lie. He spent all his money within half an hour and then expected me to buy the rest of his drinks. Trying to make conversation, I asked him what he does with his time.
Turns out he’s “a Mexican wrestler, with masks and stuff.” I kid you not. Eventually, when it had been long enough that it was polite to leave, I made an excuse and he insisted on walking me to my bus. I made it clear I didn’t need him to, and to make sure he gets his own bus. As my bus showed up, he declares he’s missed his and wants to come home with me.
He launches himself at me to kiss me. I dodged and hopped on the bus in a panic and left him behind as he shouted at me, calling me a dirty tease. Worst date ever.
I matched with a girl and sent a lot of messages. Later that night we talked on the phone and the conversation was going really well so I asked to go out the next night. She agreed and then five minutes later she tells me that needs to tell me something. She tells me that she’s permanently in a wheelchair. So, I’m either a jerk if I back out now or a jerk if I lead her on.
I figure why not? It’s just a date and it could be a fun time still. We talk more that night and go to bed, the next morning she calls me early and tells me she’s doing something crazy. She won’t tell me what but she said she’ll show me later. A few hours go by and she calls me back and tells me she’s going to send me a pic of what she did—and my blood runs cold.
I check my messages and I see a picture of her wrist with my name now tattooed on it. We end the call and I immediately tell my friends about this crazy girl. Later that night I’m driving to her place because I figure, she can be committed enough to tattoo my name on her, I should be committed enough to go on this date. Plus, I have to know it it’s real.
I’m almost at her place and I realize that my car may not accommodate her wheelchair and I know she drives so I ask if she can drive us. I’m walking in the parking lot and she drives up and I get in the car. Now I had figured she had a handicapped enabled car. Nope. It turns out she just uses two crutches to drive, one on the gas and one on the brake. I don’t like this as we’re driving on the southern California freeways in traffic.
We go eat and she gets a phone call from her daughter. This is where things completely went off the rails. It turns out she left her 10-year-old daughter at home alone and she’s scared. I’m like hey we can go. But she’s like no it’s okay I gave her something to make her sleep she’ll be asleep soon. So, we finish up and I was going take her to see a movie, but the kid thing was too much so we head home and my fingers are already crossed that we make it when she turns to me while driving and says “Wow, I’m kind of drunk!”
In my head I’m like, one drink is all you had! But I ask if I can drive and she says no she’s going get in the fast lane and uses her crutch to hit the gas. I say my last prayers but we made it back to her place. So, I wheeled her back to her door said goodbye and lived. Tattoo was real though.
47. Stealing Waves
I matched with this cute girl a few years back and we went out for drinks. It was going well and we decided to head out to the beach with a six pack to star gaze and make out. Somehow, we ended up on a stolen sailboat at 2 AM with her ex, an old drunken boat repairman who made copies of the keys to steal the boat, and her dog.
After arguing with her ex for thirty minutes she blacks out and falls asleep. Her dog is scared out of its mind and is pooping everywhere. Her ex starts tripping on acid and yells at me that I have to take care of her and never hurt her, then runs to the bow of the boat to finish his trip. The old drunken boat thief is just chilling and chugging vodka like it was water. I said screw this, cleaned up after the dog, and brought the poor pup inside the cabin with me, then passed out.
The next morning, I woke up to the girl and her ex screaming at each other about some car crash and whose fault it was. The old boat thief was gone and I had no clue where I parked. I left without them noticing, got some coffee and breakfast, and wandered around the harbor until I found my car. Never talked with her again, but I didn’t delete Tinder.
48. A Series Of Unfortunate Events
I went on a date with this guy who asked me out to get breakfast. He decided that a fast-food place was a suitable place to go. First of all, he was an incredibly irresponsible driver; he was on his phone the whole time and would speed regularly and I think he even drove through a red light. All this to not even go in because he didn’t want to pay for $3 parking.
So, we went back to his house. He was living with three other roommates (all girls) and his room was in the basement. Anyways, he was bragging all morning about how he cleaned his room just for me but when I got there, it was hardly clean and he had set out three Playboy magazines on his dresser for display. Despite being uncomfortable, I thought, “Well it’s already been this long, better finish the date.”
Bad idea. He puts on a Western-style TV show without checking what I’d like and cuddles up next to me. He didn’t smell the best and he kept rubbing my arm in some kind of affectionate way. He also kept asking me heavy questions and stuff about my ex. We finish an episode and I’m determined to get out of his place as quick as possible.
But before I go, he stops me and asks me out to dinner for another date. I refuse (obviously as I wasn’t having a good time) and his last trying words were, “I would have paid.”
49. Mission Failed
I wasn’t feeling great, but decided to meet anyway. We met at a Belgian beer bar. She was gorgeous, fun, and totally into me. I felt a gas pain, so I leaned forward slightly to quietly relieve the pressure. I completely and explosively pooped myself. The odor was immediate. I excused myself to the bathroom, but the damage was too great.
I walked out of the bathroom, muddy-panted, out of the bar, and boarded the train for home. The date was nothing compared to the horror of the following three weeks, recovering from E-coli.
50. Chuck Palahniuk, Eat Your Heart Out
I was sitting in a hot tub. It was about the third or fourth time I hung out with this girl. Everything was going great and we were making great conversation. I was really getting to know her. Out of nowhere, she says, “I want to let you in on something I haven’t told anyone.” I say okay, and she drops this on me.
She goes: “When I was six years old, my best friend and I were having fun in a hot tub. We were doing handstands just being kids. Well, she got her hair stuck in the bottom vent and drowned. I tried to pull her out but I was too young and weak. So, I ran to get my parents. They couldn’t get her out… But the paramedics got her free by cutting off some of her hair.”
I was shocked and didn’t have any idea what to say. I told her I was sorry that happened and asked if she wanted to get out if the hot tub. She wanted to stay in. After an hour or so, we ended up hooking up in the hot tub. I still don’t understand how you can’t pull someone out of a hot tub in a life or death situation like that. But then again, what do I know about hot tub vents?
51. Seems Like The Wrong Approach
One of the worst dates I’ve been on was with this guy from an internet dating site. We hit it off fine online, and decided to meet in a coffee shop in the middle of the city. We figured if we liked each other, we would go to a nice restaurant nearby. Well, he’s super awkward in person. It looked like he didn’t try to look nice at all or even shower.
I try to just talk the normal topics and when I mentioned I was a nurse he’s like, “Oh, aren’t you guys basically custodians?” I wasn’t sure if he was making a bad joke or not. I decided to ignore it and I mentioned how excited I am to finally start my dream job in a new city. He then says, “Wow, I can’t believe your dream was to get coffee for doctors!”
At this point, I get up to leave. He tries to stop me, and then I made the perfect comeback. I told him, “You are not NEARLY hot enough to get away with negging.” I went across the street to the food hall and proceeded to have a grand time by myself.
52. At Least There Was A Discount
He’s late, but only about 20 minutes, so I just brush it off. We get in the car and I notice he’s extra animated and talkative, but chalk it up to nerves. I ask him where we’re going and he tells me Chili’s because his friend works there and will give us a discount. I’m a little overdressed for that, but I’ll roll with it. We get there, sit at the bar, and he immediately orders.
He gets a shot and a cocktail, an appetizer, and his meal. Before our meal comes, he’s finished his shot, plus two cocktails. Throughout our meal, he’s talking nonstop to his bartender friend while slamming drinks. His friend tries to include me in the conversation several times but my date would just talk over me or barely let me finish my statement before raucously carrying on.
Finally, it’s time to go so we get the bill and he tells his friend to just split it down the middle, even though all I had was a tea and then a dollar appetizer. I’m pretty annoyed at this point, but just want to get out of there so I pay the 40-dollar tab. I look over and notice that he only left a small tip, even though his friend gave him a serious discount.
As a bartender myself, this was just beyond insulting, so I throw a 20 on top of the 15 I’d already tipped. I offered to drive back because of how much he’d had to drink, but he seemed totally unfazed by the copious number of substances he’d imbibed and opted to drive himself. He talked my ear off the entire drive, while I gripped the door handle the whole way home.
We park in front of my house and he leans in, I thought for a kiss, so I instinctively pulled back. Turns out he was just reaching for the glove compartment for his coke while asking me if I partake. I tell him that’s not my thing and he asks where we’re going after this. I tell him I’m pretty tired and have a ton of homework so I’m calling it a night.
He proceeds to sit in my driveway for 20 minutes doing blow and as soon as he’s gone, I practically ran to my little neighborhood bar that was about a block away.
53. Running Away to Narnia
I got set up with the daughter of one of my parents’ friends. I wasn’t really looking forward to it, but I was on break from college, and she apparently went to school not far from me, so it wasn’t like a lost-cause summer romance type thing. They showed me pictures and said nice things about her. I picked her up from her parents’ place (we were both home for the summer) and was a little surprised by how pretty she was.
The pictures had been from when she was in high school, and didn’t do her justice. The date was dinner and a movie. Dinner went really well; we had a lot in common, she was very grounded and down-to-earth, cared about the environment. If I have a type, she was it. So, as we’re walking to the movie theater, I slipped my arm around her waist.
She pushed me away and got all serious. “I’m really sorry, because you seem like a nice guy, but…I’m a lesbian. I just went out with you to make my parents happy.” Sitting through The Chronicles of Narnia with her was the most awkward two hours of my life.
54. Trivial Concerns
He picked a bar across from his house so he could drink as much as he wanted. He brought a friend. He spoke mostly to his friend about sports. He talked throughout the bar trivia, rudely. He didn’t know any trivia answers (my most petty point of contention). He asked me to drive him home, despite living a three-minute walk away.
THEN after all that, HE TRIED TO KISS ME when I dropped him off. I blocked his number after he got out of the car.
55. Ah, Young Love
I went out with a girl when we were probably young teens. We went to see Inception. She gets up to go to the bathroom, but doesn’t come back for a long time. Eventually, I go look for her, and the guy behind the concession stand looks at me and gives me the most pitying look I’ve ever received, and points around the corner. I can’t unsee what I discovered.
Following his direction, I found her making out with another guy. I should have walked out then, but instead, I went back to my seat to watch the rest of the movie. She returned and asked me to fill her in on the last hour. Also, because that wasn’t enough, after the movie I wasn’t sure what bus to take home, and she pointed me to the wrong bus.
56. Too Much HGTV
She looked nothing like her picture, not ugly, just completely different. She picked the worst restaurant in town, which I looked past because everyone has different tastes. We came back to my house and she complained about me not showing affection or touching her, so I started touching her and then she got mad. The final straw was when she decided she didn’t like my house, which I had just bought and was proud of.
She immediately wanted to go to the hardware store to buy stuff to start remodeling. It was by far my worst and weirdest date and I hope she found a house to remodel.
57. Words Mean Different Things To Different People
We went to see The Italian Job, and he talked through the entire thing, all ridiculous smug nonsense about how he would have been better at being a criminal than they were, if he really wanted to. Afterward, I wanted to go home but he drove me to his house anyway. I had no idea where I was, so I just sat and waited for him to get bored of me and take me home.
It took hours. He got into his hot tub and talked endlessly about how smart and rich and awesome he was while I just sat there making noncommittal noises, literally trying to be as boring as possible. Finally, he agreed to drive me home. He tried to kiss me in the car and I flinched away. He told me it was a shame I was too immature for him. Yeah, what a shame.
58. Big Fish in a Small Pond
I’m chick of the fatter variety and I always post a current body shot because I don’t like people wasting my time if they’re not going to be into me. So, I was talking to this guy who seemed nice enough and he asked me to buy me dinner. Ok sure. He had only posted a face shot. When we met, he was easily clearing over 450 lbs. I wasn’t really into that but I stuck it out because he seemed like a nice person.
We get coffee first and then walked over to the restaurant. Now, I’m no athlete but I do like to hike and rough woods camp. I may not be winning any marathons but I can walk for miles. This poor dude was wheezing within 20 feet of walking. Clearly it was an effort for him. I felt bad for the guy, and I try to be open-minded, but I can’t date someone that unhealthy. We get to the restaurant, which was really good, and he tells me about himself and his life.
He told me about his roommate who was dating a crack head. They would sleep together all over the place with the doors open, do all kinds of hard drugs, and were just slovenly jerks. He also told me he was a Dom and started to imply we could go make out later and he would top me. I said I had to leave after dinner and scooted as soon as it was polite to do so. The story does not end there though—it just gets crazier.
6-7 months later I try my luck again, this time with a photographer. We got along ok, conversation went well, and in the course of the date he asked me about bad dates I’ve been on. I brought up the larger guy from before and mentioned the wheezing and the pushing to top me, and he asked if the guy was named XXX. It turns out I was on a date with the guy’s roommate.
I don’t use dating sites anymore.
59. Doggone Reality
I matched with a cute girl who seemed to have all the same nerdy hobbies as I did. We set up a date at a bar close to my place. We had GREAT conversation over text, so I assumed it would go the same in person. Boy was I wrong. She barely said a single word even with my prompting her with conversation starting questions and finally she goes, “you’re a dog person, aren’t you?” I blinked a little confused and just said, “yeah?” And she goes, “yeah I could tell, you’re way too excitable and I’m a cat person.” I mean, fine? We can like different animals, right?
But THEN she goes on and on about how she’s just like a cat and how me being a dog just wouldn’t work. From then on out anything we talked about would lead back to her being a cat and me being a dog. It got WEIRD. I finished my beer and told her I had to be up early and left. I still don’t know how the great text conversations led to THAT but hey, what do I know? I’m just a dumb dog.
60. Broadcasting Her Business
I was on a lunch date with a recently divorced woman, in a low booth at the restaurant, which was closely packed with tables. She was one of those naturally loud people. She went on a long rant about how she was tired of hopping into bed with every guy she dated, she wasn’t doing that anymore, and from now on she wasn’t ever going to sleep with a guy until they were engaged.
61. Un-Navy-like Behavior
I went on a date with a Navy boy who seemed smart and sweet online. He picks me up in this incredibly ostentatious yellow Camaro, which I have the sneaking suspicion he borrowed, as it was a stick and dude was having a heckuva time driving it. We decide to go walk on the boardwalk for a while, so he pulls into a parking garage. In his attempt to park the car, he completely sideswipes the car next to us—leaving yellow paint all across their car.
He didn’t even act like anything happened, so I say, “Umm, I think you may have hit the car next to us.” He gets out looks at it, then climbs back in and goes, “I guess we should park somewhere else,” and peels out before I could even say anything. Fast forward, the date is going poorly (a hit and run is never a good start) and it’s miserably hot out so we decide to see a movie. It happened to be Shrek The Final Chapter—a kid’s movie.
He has his feet on the seats in front of us, which is no big deal, until a dad holding his toddler daughter comes in and the only seats still open are the ones in front of us. The dad goes to sit down; Navy boy doesn’t move his feet. In fact, he even moves his feet forward a bit so that he hits the dad in the head. The dad looks back at us, and then Navy boy sighs heavily, takes his feet down, looks at me and goes, “My feet were there first.”
After the movie he asked if I wanted to go to dinner, I said no, he drops me off and asks when he can see me again, he had a great time. Married five years now! Just kidding, I took mental note of his license plates and called the parking garage. I did not him see again.
62. Going the Extra Mile
After getting out of an incredibly long and unpleasant marriage, my mom joined Tinder. Stella wanted to get her groove back, and I was 100% on her team. I can’t emphasize enough that she was not looking for a long-term connection. Her work sent her out of state for a while and everything seemed perfect. She’s going to get her rando D and there’s no chance of it getting serious. She’s sending me screenshots of the guys she’s considering and I’m giving her tips on safety.
And then she picks a guy. I immediately tell her that he is not a wise choice. This guy’s profile is 98% red flags by volume. Whatever, she’s an adult, I literally cannot stop her. Somehow in the four hours they are physically together he figures out which flight she’s taking the next day. He used that to find her final destination, and somehow even finds her home address. He uses the public tax information to find her full name, and from there hunts down her Facebook.
And he finds my dad. Calls him on the phone!! And dishes E V E R Y T H I N G. Sends him pictures and screenshots of convos. Then he starts sending my mom harassing messages that he loves her but that he can’t trust her. Ultimately my mom had to call the police.
63. Tolls Must Be Paid
I had been “dating” a girl online for eight months in my early 20s. We live in different countries (America and Canada), so it was difficult to make plans to meet and have a real date. We finally decided to meet up on New Year’s in her area. Now, I had never been outside the country by myself or had any real travel experience outside of family vacations growing up.
I drove up there and made it to the border with relatively no issues other than finding out tolls still were cash only on my way through. This was the start of my troubles. I had to stop at a shady-looking ATM to pay for the tolls, and my bank unbeknownst to me decided to freeze my bank card for possible fraud after I made the withdrawal.
I get into Canada and my phone lost service because even though my company operated in Canada too, the towers just didn’t work with their American counterparts. I was pretty lost driving through the city and around the suburbs looking for the coffee shop we planned to meet at. I arrive over an hour late with no way to contact my date.
I sat for 20 minutes desperately trying to connect to the WIFI to get any sort of message out. Thankfully she was still waiting around the area and still wanted to meet. We spent an hour just talking and making plans for what to do the rest of the day, starting with checking into the hotel. I had reserved a very nice room in a highly rated hotel around the corner.
Hotels need a card on file and do a $100 hold on it in order for you to check into your room. I tried using my bank card at first, declined. Tried using my credit card, declined. I had no other cards and they would not take my date’s card as her name wasn’t on the room. My phone did not work either so I couldn’t call my bank’s support line.
Date’s phone wouldn’t connect to the numbers either. It was now late afternoon on New Year’s Eve. We have no hotel room, no money, and it was freezing outside. We still had the rest of the weekend like we planned. She is an angel though and paid for everything, including food, gas, and a hotel room. Somehow, we’re still together six years later.
64. Lifelong Memories
The first red flag was that he didn’t really look like his pictures and he had gained a pretty good amount of weight, but I looked past it because that doesn’t mean that we couldn’t be a good match. Immediately he started talking about his ex-wife who he had divorced a couple of years ago, but rather than refer to her as his “ex-wife” he kept calling her his “wife,” present tense. I had to double check that they were actually divorced twice.
We actually got along pretty well and I was having a good time despite this weirdness. We got into talking about our past more, and he proceeded to roll up his sleeves to show me the gnarliest track marks I have ever seen. He told me he was clean for about six months but had a pretty bad addiction, blown out most of his veins, and OD’d more than once. At this point I was pretty tipsy, and I knew that I wasn’t going to see this guy again but I ended up going back with him.
At his place he ended up mentioning that he had some drugs stashed away “just in case” and even though I had just met this guy I knew this was a huge problem. After about an hour of convincing, I got him to flush it. I never saw him again, but he texted me the next morning thanking me pretty profusely. It was a crazy experience, but definitely ended well! Glad I was able to help him out, and have a fun night too!
65. Dodged A Bullet
I got set up on a blind date by some friends several years before my wife and I started dating. The date was early September and we met in a restaurant in the city. It was a nice place, the kind where the wait staff wear dress shirts, ties, etc. I was in a nice suit and tie, while she showed up to our date in jeans, flip flops, and a hoodie.
I jokingly said something along the lines of, “I’m assuming they didn’t tell you this place is sort of snooty?” She goes, “They did. I didn’t care. I ain’t shaving my legs and putting on some fancy dress for some guy who I don’t even know if I like, let alone if I’m willing to let him between my legs.” I just stared at her in disbelief. But she was just getting started.
She then said, “I mean, you seem nice and all. But I ain’t in the mood to do all that work when I can just go home and do it myself.” At this point, I asked her to keep her voice down because she was getting quite loud and she goes, “WHY DO YOU WANT ME TO KEEP MY VOICE DOWN?! YOU AFRAID PEOPLE WILL HEAR ME TALKING ABOUT GOING HOME AND PLEASING MYSELF WITH MY VIBRATOR INSTEAD OF LETTING YOU COME BACK AND DO ME?!”
I mean, I get it in some ways. It’s hard being a woman. But lady….we just met. I just stood up, walked over to the waiter, paid for the drink I had while waiting, apologized to them for her outbursts, and said, “Blind date… I’m not sticking around.” I did hear from our mutual friends that she later got married to some guy, attacked him on their anniversary a few years later, and is now behind bars.
66. Gone with the Wind
My buddy hooked up with this girl he’d been talking to for a while. They met early in the afternoon on a Sunday for a walk in the park. Sunny spring day, things are going well. He’d been out drinking the day before and his stomach starts acting up and he realizes he needs to pass gas. This one will not only smell but will probably be loud as well. He spots a tin can a few yards down the pathway, and gets this brilliant idea that he’s going to kick it simultaneously with his gas to cover up the sound.
So, he runs up to the can, to get a few yards between them, takes aim and kicks, and misses the can. The effort only increases the volume. On top of it all he realized he probably pooped his pants a little bit as well. Without hesitation he just keeps on running and doesn’t look back. From her perspective, she’s having a nice walk with this guy who suddenly starts running, kicks in the air, rips a huge one, and keeps running Forrest Gump style.
67. Stranger Than Fiction
I went out with a really gorgeous girl who I didn’t know was bipolar and off her meds. She wanted to drive, so we took her car. We went to dinner, which was fine, and then a movie, where she got more and more agitated and then excused herself. I thought she was going to a bathroom, then said out loud, “No, she’s bugging out,” and walked out and found her in the parking lot searching for her car.
She screamed at me that I’d been making fun of her, the people in the theater had been making fun of her, and the people in the movie had been making fun of her. I got her calmed down and got her home, and on the way found out that she was bipolar, she had stopped taking her meds, she was into self-harm, and the car was stolen.
She kept calling after that asking when we were going to go out again. Nope, nope, nope.
68. We Love A Dog Person
My first Tinder date ever, I met this man for a drink and ended up at his place nearby. I asked where the toilet is and he responded with, “Oh you’re not going to use the facilities unless I wash you.” Genuinely thought it was a joke and said I won’t be needing his company or any sort of assistance when it comes to going to the loo.
I came back out and asked for water, and he pointed towards a dog bowl on the floor and told me to use it. “Jesus, what the heck, man?!” must’ve been close to what I was thinking right then. No kink-shaming, here but perhaps try initiating some sort of conversation about your puppy play preferences PRIOR to trying to force your kinks on your date?!
Anyway, he obviously wasn’t getting any less creepy but it was getting very late and I was stupidly young and naive so for some reason I ended up sleeping over and leaving in the morning. He wanted me to put a collar on me for the night although I’d already declined the bowl and whatever other suggestions he was making about that.
69. The Dutch Have The Right Idea
I matched with a girl on Tinder, and she was picky with the restaurants we were going to meet at. I just let her choose. I had to take an hour on transit to get there, and I reached the place 15 minutes late due to my bus stopping too long at stops. She wasn’t in the restaurant, and when I messaged her, she chastised me and started hurling insults, saying I didn’t value her time.
Still thinking it’s my mistake, I apologized to her and told her to come back. She does, and the minute after exchanging pleasantries she instantly ordered $90-100 worth of food even though we were both students at the time. To keep the cost low, I ordered myself a small salad. The rest of the date was bland with her giving one-word replies with a frowny face.
I lost interest and patience. At the end, the bill was $150 and I asked her if she could split, even though mine was only $20. She created a scene and insulted me in front of everyone. The kicker was she ate only 50% of food she ordered and tried to get a takeaway. At that point, I said, “No freaking way,” and took the food home for myself.
70. First Date in a Dream State
This happened before Tinder during the transition between Myspace and Facebook eras. I meet a girl on Myspace and agree to meet at a local bar where I’m friends with the bartender and lots of people. She is from the other side of town. At the time the “Sparks” drink is all the rage and is a combo of a super strong energy drink and malt liquor similar to fourloko.
We really hit it off and are crushing tons of these drinks which are packed with caffeine. The bar closes and we go back to my place, sleep together, and pass out somehow. Eventually I wake up to her naked walking out of the bedroom and naturally assume she went to the bathroom, but she never comes back. Finally, 20 minutes or so later, I get up and search the house. I get to my garage and my car is missing.
Then I get a call from her mom. She had driven my car, which was a manual, half way home and got it stuck on a tall sidewalk and smoked the clutch. The police came and she was naked and not coherent. They booked her for a DUI but all agreed that she was sleep-walking probably due to the mass amounts of caffeine. She was super apologetic and her grandfather paid for the damage to the car. I gave her another shot and we’ve been married for 10 years, have three sons, and a hilarious first date story.
71. Gotta Have A Sense Of Humor
I met a girl through a dating site and we agreed to meet up for dinner. I learned very quickly that this girl had absolutely no sense of humor whatsoever. I don’t even think she cracked a smile the entire night. The date just got more and more painful as the night went on. So at one point during it, we were talking about online dating.
She told me about a friend of hers who went out on a first date with a guy online. She said this crazy guy fell absolutely in love with her friend and said he wanted to marry her. So, I said, “Oh, well, I guess I shouldn’t have picked up this engagement ring on the way here, then!” She just stared at me blankly and said “That’s not funny.”
72. Short Getaway
My friend matched with a guy and turned up to their date. He told her he was 6 ft. and was WAY shorter than that. Then he kept telling her how he would murder someone and get away with it during the entire date. There was no second one.
73. Wrong Attitude
When we ordered drinks, she wanted a drink with some brand I’ve never heard of and when they didn’t have it, she gave the server some attitude. When we get the food, she asked for ranch for a pasta dish because obviously, they didn’t bring ranch in the first place because that’s kind of weird. So the waitress is like, “Yes no problem, be right back!”
And this girl replied, “Be fast please so I can eat it hot.” After the waitress left, I asked her if she was doing okay because that was kind of rude and it would be fine if she wanted to go home. She basically told me that she can talk to them however she wants because she was paying them. When the waitress came back, I asked for the check and a box and left.
74. Nuts About You(SSR)
This girl I went out with would not shut up about her love of communism and her hatred of peanuts. For three hours every single subject I brought up somehow turned into either how we need a new Soviet Union or how peanuts are the worst thing ever. She wasn’t allergic or anything. She just for some reason really, really hated peanuts.
She ordered a very expensive non-alcoholic cocktail and then didn’t split the bill, all I had was a single Heineken. She was also a bit of a catfish as she was hardly as attractive as the pictures, but I’d roll with it, except for the peanut thing. Why peanuts? Sometimes I remember and wonder. Peanuts?
75. Lock Up Your Valuables
I was on vacation in Miami and met a girl at bar. We went on a date the following day and ended up both naked in the hotel pool at 2 am, as one does. She told me she needed to pee and grabbed the room key. This was my absolute worst mistake. After waiting 30 minutes, I went to lobby to get a towel and a room key. When I got in, she’d taken everything.
Phone, suitcase, clothes, money, passport…everything. My friend picked me up at the airport in my sorry state, and he couldn’t stop laughing for a year. The thought of me naked in Miami with nothing…
76. All Over It
I met a girl from Tinder and we saw each other a few times. She had an ex that she still talked to, but hadn’t had any feelings for in a few years. So, I go to her apartment and this place is like a shrine to him with pictures of him on every wall. And it wasn’t just from when they were together and she never took them down.
She just moved to this place a month prior so she recently decorated her apartment with his face. It really creeped me out and felt like I was going to be some sort of sacrifice to get him back.
77. What A Mess
I met this guy online a few years ago and we chatted semi-regularly, mostly about films and other interests we had. We lived in different towns so the idea of a date was never brought up, but I enjoyed talking to him. Then this one time I was going to visit his hometown, so I messaged him. He agreed to meet and even offered a place to stay for the night.
We met at the train station, and I immediately noticed he was wearing dirty clothes and hadn’t washed his hair in probably days. His home also reflected this untidiness. I had nowhere else to go, though, and it was getting late so I decided to just power through it. We mainly just watched old episodes of television shows in growing awkwardness.
He had bought some vino and after having two glasses he became very touchy. He started sitting closer to me and offered the worst shoulder massage of my life (it simply hurt A LOT). I tried my best at maintaining a distance and then straight-up had to tell him I wasn’t ready for anything when he said he was trying to kiss me and “I was making it very difficult for him to do so.”
I said it’s just best if we go to sleep and proceeded to remove my makeup. Then he really embarrassed himself. He said he had never seen a woman do this and he legit said “ew.” After that, I thought it couldn’t get any worse but…he had lied about having a guest bed. I ended up sleeping fully clothed in a dusty floor after rejecting his cuddle attempts and left the next morning as soon as the sun rose.
I work at a fast-food, casual restaurant with counter service like a hot dog joint but has a nicer than a McDonald’s vibe. I was at work when I noticed a girl that I matched with on Tinder a few months prior was in the dining room with a friend. We talked for a bit but never met up or anything and stopped talking a few days later.
She didn’t recognize me and I didn’t expect her to so I didn’t say anything. I go over to wipe the table next to where she’s sitting as someone had just got up. As I’m wiping the table I over hear her telling her friend how she gave some guy chlamydia. I’ve never had a sense of relief in my life like I did in that moment. Thank god I never met up with this girl.
79. Please Stop Talking
I met this guy on the internet. He seemed like a cool guy and I agreed to meet him for dinner and drinks. Things were going well until we went to a bar. His first comment upon sitting down was, “Sorry I didn’t expect this place to be such white trash,” and kept mean-mugging some ladies sitting at the bar. I asked what he meant by that.
He said the ladies at the bar were too old to be wearing low-cut shirts and bedazzled jeans. Now, these beautiful ladies were not old, and even then, who cares what they were wearing? I was also wearing a low-cut shirt, to which I pointed at puzzlingly, and he replied, “Yeah, but you’re young and cute.” I stayed a little longer and he just kept showing me how much of an angry person he was.
The last straw was that he kept pressuring me to take shots when I didn’t want to, then chastised me when I told him I was feeling tipsy. That’s when I got my purse and told him I was leaving. I guess he didn’t think I had the gall, but it felt nice hearing him yell, “Are you serious?!! You’re leaving?!” I laughed as I got into my car.
80. Catching the Crazies
Two years ago, I matched with this guy who seemed like a dream on paper. He was good-looking, just a year older, and extremely financially successful. He had made millions of dollars through a software invention. I was so excited because I’d been out on a lot of first dates with wealthy, soulless guys, or guys without their act together, and I wanted to meet someone more like me.
When we met in person, something about him was so off. He seemed like he hadn’t showered in a few days, he had this large gold chain across his neck, and he even talked a little to himself. The conversation we had was the craziest one I think I’ve ever had with anybody ever and I work with traumatized children who’ve been displaced from their homes.
He believed in conspiracy theories, in astrology, and even that he had psychic powers. The whole date, he kept telling me about his powers, his luck, and how whenever he wanted someone to work for him, he just imagined them, and they’d show up in their office. He also believed Anderson Cooper was a lizard person.
After about two hours of all of this weird, but interesting talk, I left. He messaged me immediately after asking for a second date. I said no, and he asked me if I wanted to take a $10,000 trip to Paris with him. I said no again. He offered me a $150,000 a year role at his company. I said no. He offered me $400,000. I told him no and wished him well.
For about six to eight months after, he would message me about once every two months, to tell me about tech deals he’d closed, to charity work he’d done, to pictures of himself in exotic locations. He would ask me for advice about his charity and his life.
Finally, he disappeared from my phone. He sometimes appears in my “you might consider following” lists on Instagram but I blocked all of his accounts. What a weird guy.
81. The Wrong Route
She was working as a DJ. I met up with her after her show and we were heading to a diner to get some food and catch up. We had to cut through a nasty, dangerous part of Philadelphia, and I had a brand-new car with a manual transmission. For some reason, the clutch failed and wouldn’t engage. The car was stalled in Philly’s murder capital.
I’m now trying to find a tow that would even come to this part of the city at 3 am. But her actions were worse. She bails. her parting words being, “you’re hot and all but I’m not dying just because you’re good-looking.”
82. Dealings with the Devil
I met a seemingly nice girl on Tinder. We dated for 2 months. It was 2 months of pure torment. After the 3rd date, she started telling me things about myself that no one could ever know. The kind of secrets that one would bring to the grave. I pressured her and asked her how she knew. She finally admitted that she practiced black magic.
In the following weeks, she threatened to blackmail me, cursed my entire family even though they did nothing, got paranoid and accused me of cheating when I spent most of my time driving for work, and demanded relations whenever she wanted—even when she was angry. Once time, her voice changed to something screechy and raspy and I think I might been sleeping with a demon.
I had enough and forced myself to break up with her after 2 months. Deactivated all my social media accounts and went off the radar for a while after that, until I found out that she had a new guy to mess around with.
83. Misplaced Guilt
My date showed up 35 minutes late to the restaurant. We had mediocre conversation. I told her I was legally separated, awaiting the final divorce, but still sharing a house with my ex while the ex was closing on her new property. By the way, our divorce was amicable. She lost it on me, telling me I was a terrible person. Fine. If that’s not your bag, no biggie.
I walked her to her car since this wasn’t going anywhere. When I saw it, my eyes went wide. Her car was filled with trash. Like, filled, except the driver’s seat. She then contacted me a few days later and said she changed her mind and wanted to go on a date. So, we set one up. She no-showed, but called me and said she felt a little guilty because she was STILL MARRIED. She’s a divorce attorney now.
84. Do You Like-Like Me?
I met a woman who I really hit it off with. There was no physical affection for maybe six months of just hanging out several times a week as friends. One night we got hammered and I spent the night. After that, we still hung out just as frequently, spent the night every time, and we pretty much acted as a couple—going out with friends, wedding dates, etc, etc. I had things that lived at her place.
After maybe 6 months of this, I found out on the other 2-3 nights each week we weren’t together, she was hooking up with randoms on Tinder. Apparently, even in your 40s, it’s necessary to have that “so, like, are you officially my girlfriend?” conversation that you had to have in 6th grade.
85. Don’t Play Games
He met me at PF Chang’s (which he picked) and complained about the cost of everything. When I offered to go Dutch, he got weirdly offended. He gave me a lengthy analysis of why I was “so hot” but also included my flaws despite my efforts to change the subject. By the time our food came he was sweating so profusely, his shirt was soaked through at the armpits and collar.
It was a gray shirt, which made things exponentially worse. He negged me constantly and I called him out on it and asked if he was trying some pick-up artist moves. He fumbled with an explanation before fessing up that he was trying the techniques on me. He insisted on paying (complaining the whole time) and walked me out to my car.
He was trembling pretty badly all throughout the date, and every time I noticed, it worsened. I politely said thank you and he went in pretty aggressively for a kiss. Like a surprise attack. I dodged and said that I do not kiss on the first date and he said, “Aw, come on!” And tried to kiss me again. I shielded my face and got into my car and drove away.
86. No Signs of a Threat
A cute girl from OkCupid offered to pick me up for our first date and we hung out with some of her friends at the mall. Then we went driving around town having a ton of fun, getting fast food, talking, stargazing, the works. She goes to drop me off and I wanted to kiss her. Things started getting a little heavy and she stops me just as we’re thinking of fooling around in her car. We cooled off, said our goodnights, and she left.
The next day I texted her and she didn’t respond. Later on in the night, she finally called me. It was the most terrifying phone call of my life. She sounded a little awkward, and blurted out, “Hey, I just wanted to tell you I had a great time last night. But I’m going to kill myself now so I wanted to say goodbye before I do it.” WHAT?! I frantically tried to call her back.
She didn’t answer. Eventually, after a few more tries, she picked up again. I’m yelling at her and she’s just responding to me like this is normal for her. “I’m sitting on top of a bridge right now. As soon as the train comes, I’m throwing myself in front of it.” She hangs up again. I’m freaked out.
The only thing I could think to do was call 911, so I did. I got them to transfer me to her town’s 911 branch, and they ended up connecting me with the police chief of the town. He and I spent the whole night with this situation. I would call this girl, trying to figure out her whereabouts, and he would dispatch officers to find her. Luckily, the police chief told me that no trains were running through the town that night, and an officer eventually picked her up walking on the street next to one of the train tracks. She was committed that night.
The last phone call I got from her was in the hospital. Her parents were furious at me because apparently, she “did this kind of thing all the time.” They were mad that I’d called the cops and they wanted me to pay the medical bills. I obviously refused, they threatened to sue me, and I hung up. Never heard from any of them again. I was so traumatized from that incident that I didn’t do online dating for a couple years. And that wasn’t the only crazy encounter with a girl from OkCupid.
87. An Absolute Spectacle
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, but all in good fun. Only…it turned out that she was bringing me there because she wanted me to be part of a documentary about foreigners in Korea. My looking like a fool was broadcast nationwide.
We then visited the grandmaster’s house for makgeolli and the film crew started interviewing me. They were basically focusing on my relationship with the girl I was going out with. They didn’t seem to understand it was a first date. So here I am trying to answer awkward questions without embarrassing both of us on national television.
88. Not A Relaxing Idea
This guy I worked with kept asking me out, and I continuously said no. After about a year, I started to feel bad for the guy and said yes to a date. He asked me to lunch so I figured it could be a quick easy “date.” He picked me up and took me to Wendy’s…where he made me order off the dollar menu…and I could only get two things.
After this very quiet lunch where he hunkered over his chicken nuggets like I would take them, he said he needed to stop at Walmart. We go in and he heads to the lotion section. Strange, but whatevs. He then grabs two scented lotions and asks which one I like better. Being nice I pick one, and he responds with, “Great! I’ll use this for your massage!”
89. Goods Unreceived
I took a girl out to dinner and she ordered a salad with nothing on it. So, she ate lettuce like a rabbit. It was terrible conversation with one-word answers and was almost like pulling teeth. That was weird but she wanted to go back to my place and watch a movie and she had a nice rack so screw it. After sitting through the atrocity that is the movie Her, we start to fool around. For 90 minutes we do middle school stuff but I’m going to be patient because you know, I want to see those cans.
Finally, she stands up, turns off the lights, and strips down. She lays on top of me and I go to make a move and she says to wait. Okay, not a problem. I lay there for 20ish minutes with my hands at my side, fully clothed as she lays butt naked, face down breathing on me. She stands up, gets dressed, turns on the lights, and leaves. Immediately deleted Tinder. Also, never got to see the goods.
90. All Business
I’ve known this guy for almost a year now, we’re not really good friends or anything, more of casual acquaintances. A couple of months ago he started messaging me, first on Facebook, then by text (he got my number from a friend, he didn’t ask me for it) and most of the time I responded just to be polite. He’s nice enough, but not really my type.
When he started dropping hints about “meeting up,” I just turned him down and said I’m busy, or we’d just catch up the next time there’s a gathering with our friends, that sort of thing. Fast-forward to last week and he asked me out again, which is the sixth time in the past two months. I finally decided to at least give him a chance, what could go wrong, and who knows what I’m missing and all that. I had no idea what I was in for.
Worst-case scenario it would be awkward, but we’ve talked more than a few times so I was thinking it can’t be that bad and we could actually have a pleasant time. Date night comes and we have dinner. I was certain at this point that it’s really not going to take off. But I was having a pleasant enough time and he was a total gentleman and not bad to talk to.
The bill comes, and I was going to suggest a quick coffee before heading home. However, he said that he’d made an appointment for us and we need to rush off to make it in time. I was a bit intrigued and excited; was it a movie, or a show, a play? So we hurry off…and he took me to a high-end luxury mall with an attached wing for offices…
It was a weight-loss center. He explains that he’s part of this company and he wanted to introduce me to their products which would “revolutionize” my lifestyle and make me healthier I’ve ever been in my entire life. I was totally stunned at this point so I was just nodding like an idiot the whole time we were walking inside. My brain hadn’t caught up.
After I flat-out said that I’m not interested in any of the products and frankly don’t believe that I need health supplements, they started on the seconnd phase: introducing me to the “business” aspect of it. Basically, it was a networking model of business where you not only sell the products, you also recruit people to sell them and they would be under your “team.”
They rhapsodized about the wonders of the product, how easy it is to sell, and how much money I could be making because they could tell I have the right kind of “personality” and “network” for it. Registration was “only” $1,000, and it was consumable in products. So, yes, a pyramid scheme. I wish I could say I flipped the table and screamed at them.
But no…right after the “talk” I just said I should head home since it was getting a bit late. The guy actually messaged me to say that he had a good time and he hopes to see me again. And that I should reconsider their products and the “business opportunity.”
91. At Least It Was A New Experience
I had a guy take me to a weird religious thing. He was uber-Catholic and thought I could benefit from letting Christ into my cold, cold, cold Jewish heart. So I go. I’m open-minded. I’m only half-Jewish and have always been interested in other religions. It was going “okay” until the priest (the speaker of the night) told us a hypothetical tale of our brother who is paralyzed.
We have the ability to cure him with stem cells, and he will walk as soon as the “transaction” is complete. “How many of you here would purchase these stem cells and allow your brother to walk again?” My hand shoots up. I look around the room… nothing. No hands. I then notice everybody staring at me. Including my date and the priest.
I was blessed out like nobody’s business and was told I was an embarrassment to my date. Good times.
92. There’s An Easier Way To Ask Someone To Leave
The absolute worst date I’ve ever had was the woman who turned up to the pub with literally no money, expecting me to buy her drinks and dinner. I wouldn’t have minded if she’d have told me beforehand, but this was completely out of the blue. So anyway, we sat there making awkward conversation, or at least I tried to start a conversation.
I told her about my life, asked her questions. She was too busy texting and phoning her friends to really take notice. So eventually we did get talking, and then out of nowhere, she told me that she had abandoned her dog. Because she felt like it. That was definitely the final straw for me, and I just upped and left and avoided all contact after.
93. Not Everyone Lies About Their Age
I saw a girl on Tinder, 21, empty bio, couple of nice pics, and I think, why not? I swipe right, it’s a match. We talk for a day and decide to meet. The first question she asks is, “So which grade are you in? I’m in ninth.” My bio said 21 as well, which I was at the time. Because, you know, I didn’t lie about my age. I couldn’t run out of there fast enough.
94. 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.”
95. Caught Red-Handed
My then boyfriend had let me use his iPad to watch a movie on Netflix. He had his messenger account linked to both his tablet and his phone, and messages kept popping up on it while I was watching without him realizing I could see. I got to watch in real time as he got his best friend’s wife to agree to sleep with him over the coming holiday weekend; with the promise that he’d get rid of me for that weekend so they could get intimate in our bed.
96. Better Now Than Later
I dated a woman for over two years before I finally decided to pop the question. The first time she said, “I don’t know.” A couple months later, I asked her again, and she said “maybe.” I was pretty bent out of shape, but then I found out the horrible reason why she turned me down. She was sleeping with several of my friends, so I guess I dodged a bullet there.
97. Bad Vibes
My ex and I stayed friendly after our breakup. He started dating someone new. After he introduced us, he asked me what I thought of her. I had a bad feeling about this girl and told him that he should be careful. The more I got to know her, the more I just had this sense that she’s bad news. He laughed it off, trying to say I was just saying that cause I still had feelings for him. I didn’t.
Few years later, he needs representation because she destroyed his business, his family, stalked and harassed him and even had him under investigation by the FBI. Took him a couple years to clean up the whole mess. I totally said I told you so.
98. 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.
99. Taking The Term “Blind Date” A Little Too Far
Not sure this counts since the date didn’t actually happen, but I was set up on a blind date. We planned to meet at a restaurant. I got there first and since it was a nice day out, I sat down on a bench outside the restaurant. He ended up calling me on his way over and I told him where I was sitting. He was still on the phone when he started walking up to the building.
He took one look at me, hung up the phone, and walked back to his car. I tried to call him back, thinking something must have happened, and he didn’t answer. No more answers to calls or texts afterward.
100. 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.
101. Eating For Two
I chatted a girl up online for about a week or so, and things went pretty well, so we decided to meet up. I asked her out for dinner, and said that if things went all right we’d go grab a drink. Let’s just say her photo didn’t match her appearance. Her excuse was that she had a crazy ex who was stalking her, so she used her sister’s photo and name.
HER NAME!!! SHE LIED ABOUT HER NAME! Anyway, come to find out through our “interview” that she was an only child. She didn’t catch her slip up, but I sure did. She rambled on and on and on about stuff I really couldn’t have cared less about. Then came the food. The waitress may as well have brought it out in a trough, as this woman didn’t use her utensils.
Did I mention we were at a steak restaurant? That’s right folks, she picked her steak up and ate it with her hands. Let’s not even get into the potatoes. It was the worst date of my life. I couldn’t eat my meal. I told her I wasn’t feeling well and that I was just going to get my food in a box to go and I’d eat it later if I felt better. Her response: “Would you mind if I ate it?”
She proceeded to devour my dinner as well. The waitress comes over and says “Goodness. When is your due date?” So she says that she is due in two months. First off, I couldn’t believe the waitress asked that, but then I was floored at the girl’s response. Unbelievable. Being the gentleman that I am, I picked up the check because hey, it wasn’t going to pay itself. I kindly said it was “nice to meet you,” got in my car, and went to the bar. Well, she followed me.
She followed me to the bar, and when I got out of my car, she proceeded to berate me over why I was going out instead of going home. Now she’s calling me a liar in the parking lot of the bar I frequent, and my work buddies are starting to roll in. I never heard the end of it. I said to heck with this, got in my car, and drove home.