Does anyone truly enjoy dating? Unless someone catches a break and meets their soulmate right off the bat, most people are going to experience more bad dates than good ones. And if they’re super unlucky, they may have multiple dates that are so bad they’ll want to retire from dating altogether. Unfortunately, that seems to be the case for these people on Reddit, as they shared dating experiences that were so strange they will cause secondhand trauma to anyone reading them, so beware!
1. Couple Seeking a Sugar Daddy
I showed up to an Internet-based date and she showed up with a dude. She expected me to pay for both of them to eat and drink for the evening.
2. Happily Ever After
I went out with a girl to a nice Japanese restaurant. I got there first and waited at the bar. She walked in, saw me, and walked out immediately without a word—but somehow, the date continued. I went outside and asked her if she was okay and she told me, “I can’t really be in there right now.” We went to an Irish pub instead and had some very awkward small talk filled with long silences.
After about 45 minutes I told her I thought it was pretty clear that this wasn’t working and we didn’t have to stay, we could just go. I took her back to her car parked at my house and we said goodnight. Right before I opened my front door she asked if I wanted to get a drink at the bar across the street. I said sure, we had a great time, got hammered, went back to my place and had a brain-melting hookup.
We’ve been married for 10 years now. She has some pretty serious anxiety issues that come and go, and for whatever reason, the crowd and atmosphere at the Japanese place really set it off and it took her some time to recover.
3. It’s Not Technically Cheating
Probably one from about five years back or so. I had just moved to London and met this guy on a dating website. He was generally not my type, but still, I was fresh out of a long-term damaging relationship and trying to meet new people, yadda, yadda. Fast forward to the date. He takes a call from a girl and he says to her, “Oh, I’m just in the pub with—male roommates name.”
I can hear her on the other end getting worked up about something and him telling her to calm down. Alarm bells are already ringing. He hangs up the phone and says, “That was my fiancé, but not a real one, just one I’m with for her visa.” At this point, I’m already thinking “bloody hell.”
He continued on with his excuse, “She also lives with me,” in his two-bedroom apartment with this other roommate—cozy. “Oh yeah, I should probably tell you I’m getting married in three weeks.” At this exact point, I just said, “Well, I’m going home,” and start pulling on my coat. His reply was even more classic: “Do you want to help me buy groceries first?”
4. Worthy of a Twitter Thread
I met a girl on Match. She showed up 20 minutes late. I had to “excuse myself” so I could hide out in the bathroom and write down as much of the crazy things this woman was saying before I forgot. Topics included, but were not limited to—Daddy issues, her mother loves her brother more, miscarriage, being married before, when “we” start dating—but it didn’t stop there.
She continued and talked about what would happen when “we” are married, setting me up with her assistant, how she’ll “screw me with blood on my face,” things she does when she’s high, Brazilian trance music, adopting children, what’s my dog’s name is again, how she doesn’t trust animated movies, why she was 20 minutes late, owning a business, when it’s acceptable to use the c-word, being a vegetarian, her blind cat, her dying uncle, abusive relationships, the city of Tampa, free-range urination, and can we order tater tots.
We didn’t go out again.
5. Fool Me Once
We had been talking on the phone for about a month already. He tells me his car is booted outside of his house. He had a long drawn out story about how he could not get the boot removed. His dad was staying with him and he thought he would be able to use his dad’s car but now he can’t. So, I go get him to go somewhere to eat. He starts panicking, saying, “Oh great, now I’m in the car with you and I’m going to get accused of rape or something.”
I asked him what the hell he was talking about. He just kept rocking in his seat anxiously and worried that he would be accused of rape. I drove to the nearest area with food and asked him where he wanted to go. He said he had no money and wanted to go home, so I took him home. Then he asked me if he could borrow $20. I don’t know why, but I gave it to him.
After this, he called me repeatedly and I ignored his calls. He texted me asking why he was “not good enough for me to date.” I kept ignoring him. Fast forward three years. He is on a dating site I am on. He messages me but does not remember who I am. He tells me that a year ago his long-time girlfriend passed away—the one he had lived with for 10 years.
So, he was not staying with his dad, and he was freaking out because he lived with his girlfriend when he met me, right outside of his house. I called him out on it and he tried to pretend I had the wrong guy, but he had the same name and worked at the same place, and looked like the same guy. Very bizarre.
6. Is This a Date?
I went on a date with a guy in my apartment block, only to see his disappointed face when my girlfriend called me on the way home. I realized he’d assumed I was gay and that I’d assumed he was just a friendly guy who wanted to hang out.
7. Call It in
I’ve posted this before because it’s so weird. I went for a meal with this girl I met through a dating app and it was going really well. We started talking about movies and then we decided to go to the cinema to go watch Inception. She said there was a cinema nearby but I didn’t know the area at all, so I used the GPS on my phone and she held it and directed me.
Once we got there we started walking inside and I realized I didn’t have my phone in my pocket. I said I must have left it in the car and started to walk back to get it. She was trying to get me to leave it and saying we would miss the film but the phone was only about a week old, so I was really paranoid about it. We checked the car for about 10 minutes but we couldn’t find it.
I asked her to check her jacket and her bag but she said it wasn’t there. A couple parked next to us so I asked them to ring my number because I couldn’t find it. It started to ring and it was obviously coming from my date’s handbag. She took it out and said she must have missed it. I thanked the couple and locked my car and as I turned back around she was walking the other way. I ran to catch up and asked what was going on but she was very dismissive and was barely talking.
That’s when I realized it wasn’t an accident and just left her to walk home alone.
8. Just Go With It
During my freshman year in college, I had a crush on a girl from my high school. When I asked her out, she informed me that she only dated women—I am male. She insisted that we were still friends but she just didn’t roll that way. She offered to be my wingman and I gladly took her up on the offer.
A few weeks later she had set me up on a semi-blind date with one of her friends—we’ll call her Monica. The three of us met at Arby’s—because we were fancy—and my friend tried playing matchmaker. “He loves theatre and so do you, Monica!” “Monica loves music and so do you!” The date was going fine, so my friend decided to leave Monica and I alone.
We talked a bit more and decided to go see a movie. I didn’t have a car at the time so I hopped in Monica’s passenger seat and we went on our way. That’s when things got weird. About two minutes after leaving Arby’s, Monica receives a phone call. She says it’s her roommate and she needs to answer it. She picks up the phone and I hear a man’s voice.
I was a bit surprised, but it’s not too unusual for a girl to have a guy for a roommate. Monica and her “roommate” get into some kind of argument, and she pulls over to a gas station. Another car pulls in right beside us. Again, I didn’t think anything of it at the time. Monica turns to me and says, “I need to go talk to my roommate. Just wait here for a minute.”
I assume she just wants to be on the phone in private, but what happens next will shock you! Monica gets out of the car and goes to talk to the driver of the car that pulled in next to us. This is where I start to freak out. What are the odds that her roommate happened to pull up right beside us?! I hear a bit of yelling and then I start thinking about an escape plan.
At this point, Monica opens my car door and says “Hey, I’m really sorry to do this but my roommate is going to have to take you home.” Now, this is the part of the movie where someone in the audience screams, “Don’t you go with him, now! That’s how you get killed! White people always going with the strange man thinking everything will just be a-okay!”
I wish I could say I got smart, said, “No thank you, I’ll just walk” and went home. But I didn’t. With some combination of confusion and curiosity, I get out of Monica’s car and head into the passenger seat of this stranger. We’re in my hometown, so I know if he goes any direction he’s not supposed to I can just bail out of the car and run to freedom.
The guy was pretty big. I was 6’2″ tall at the time and he was significantly bigger than me, if that tells you anything. I don’t remember his name, but we’ll just call him Ross. Anyway, Ross starts driving back to my dorm and we’re sitting in awkward silence for most of the trip. Eventually, he says, “So, how do you know Monica?” I knew something fishy was happening, so I wasn’t about to say we were on a date.
I just said, “Oh, we have a mutual friend!” and hoped Ross didn’t get suspicious. He just nodded his head and kept driving. Apparently, Ross was resolving some anger in his head, because out of nowhere he starts talking as if we were in the middle of a much more personal conversation. “Yeah…A lot of people at our church are upset that Monica and I live together. I think they’re just assuming we’re having sex all the time or something. It shouldn’t even matter since we’re engaged, but it’s still annoying to hear stuff like that, you know?”
I just nod my head as I realize what just happened. Apparently, my lesbian friend set me up on a blind date with an engaged girl, and her fiancé came and picked me up to take me home. I was silent for the rest of the night. I told Ross the wrong dorm so he wouldn’t know where I lived, and I got out of the car and just walked around campus for a bit.
It was definitely the strangest date I’ve ever been on.
9. Great Minds Think Alike
So I met this guy when I was in college in DC and he invited me to go to on his motorcycle to his family’s farm in rural Virginia. I told my best friend and she was appalled. “He could be an ax murderer! You could come home in a dozen pickle jars!” I pooh-poohed her and went on the two hour ride out to the farm. We get there and take a walk up the mountain behind the farm.
He’s picking me wildflowers along the way and we’re having a grand time watching the wild turkeys. As we’re walking down, there’s a fence with a tree growing next to it and I decide to swing myself over the fence like Tarzan. Unfortunately, there was a huge rock at my landing spot and I took a nasty tumble, spraining my ankle pretty badly.
We limped back to the farmhouse—really a two-room cottage—and got my boot off. It was immediately obvious I wouldn’t be getting it back on. So much for riding home that afternoon. He said, “We’ll have to spend the night here and wait for the swelling to go down.” I’m thinking, “Pickle jars…” He rides to the local IGA to pick up some food—nothing in the house—and comes back with groceries and asks, “Guess what’s for dinner?”
“Chicken Kiev,” I answered. It was the most unlikely thing I could think of at the time. His face fell. He had picked up the ingredients to make Chicken Kiev, thinking it would impress me. We should have known right then and there. We’ve now been married 31 years and have two kids.
10. Pawn in the Game
I got asked out by a girl I knew and was sort of interested in but didn’t really know all that well. We went to an open-air jazz concert, not really my thing but sure. Once we got there, she immediately was all over me—hugging, sitting on my lap, etc. Things were going great, or so I thought.
It was at that point when things started getting weird. Several band members were giving us strange looks from stage, while playing their jazz music. One piano player was mouthing things in our direction, but I couldn’t make out what he wanted. People were rude to me for no reason whatsoever while getting drinks.
Long story short—my date knew just about everyone there and wanted to get back publicly at her—very large—boyfriend for cheating on her. Don’t hate on me jazzheads, I’m just an innocent sucker! Awkward ending—I met them both later that evening at the train station and she pretended not to see me.
11. Three Stages of Hell
Okay. I have never shared this story online before, but here goes. I was going to have a second date with this girl. She knew of three parties happening on the same night, so she suggested that we hit all three. Sounded good to me, so off we go. At party one, her best friend from college is there that she hasn’t seen in four years. They immediately run off together, and I’m left with the friend’s boyfriend having a drink.
I think to myself, this is no big deal. She hasn’t seen her friend in a long time, and the night has a lot more to go. She comes back after a while and suggests we head on to the other party. Great! We arrive at the second party. My date immediately runs off with some other friends. Like, “Tim, oh my god, how are you doing,” and dashes across the party to find him.
I slowly follow behind, but then they keep scurrying on to talk to other people without the girl making it clear that she wanted me to come. I feel really awkward because she doesn’t introduce me or say anything about me. I’m just an awkward guy there that no one knows. I get tired of that and go to the bathroom, where I find that the door has been ripped off its hinges.
I find a screwdriver and fix the door before using the bathroom. Fast forward 30 minutes, my date finds me and suggests we go to the final party. But this time, her friend Tim is going to join us. Okay. We arrive at the third party. As soon as we walk in the door, Tim says he needs cigarettes, and the girl and Tim run out for cigarettes and leave me at this new party with all these other people I don’t know.
They are gone for 45 minutes, by which time I decide that this date isn’t working out and I should just go home. When my date comes back with cigarettes, I tell her I’m leaving and she FLIPS OUT. She starts screaming at me in front of everyone about how she was going to have sex with me later and how I ruined everything. Then she proceeds to scream, “you’re not leaving me, I’m leaving you,” after which she bolts out and slams the door.
Then everyone at this other party, whom I don’t know, is staring at me while my date, who brought me there, has abandoned me. Someone eventually comes over and offers me a drink. I stay for another hour and laugh it off with the people at the party. I am still friends with some of those fine people today.
12. From Man to Child
I met a guy from OkCupid. The first time, we met up in a public place and just had a casual chat. It wasn’t a horrible date, but it wasn’t very memorable either. I decided to give him another try because it could have just been nerves. The second date, he invited me over to his place. I knew he lived with his parents, but I kind of assumed they’d be away.
They weren’t away. They kept coming into the lounge room and giving us iced tea and chips whilst he played Xbox in his track pants—no shirt—and I sat there awkwardly watching. He didn’t really speak much to me. It was 11 PM, and he was in his 30s.
13. Friendly Date
A friend set up a double date with a girl he was dating sophomore year of college, and she said she’d bring her friend, who she explicitly said was a female friend. My buddy and I met her and her friend at a bowling alley for rock and bowl. She had brought her cousin—her male cousin. Who was 15 years old. Then she basically just spent the whole time talking to her cousin and ignoring my friend.
So, my friend and I just had a heck of a fun time bowling and chatting it up with the other people at the alley. Then we all went to get late-night appetizers from Applebee’s and she ignored my friend the whole time as well, so we made it our goal to make the waitress/waiters around us laugh as much as possible. My friend and I headed back to his mom’s so I could get my car and we told his mom what happened.
She was like, “So, you two basically went on a date with each other.”
14. Sometimes Judge a Book by Its Cover
I met a guy online—of course—and after talking for a couple of weeks we decide to go out. I meet him at his house because—supposedly—his car broke down that morning. This guy is dressed like an extra greasy version of the Fonz. I try to look past this but secretly I’m devising ways I can destroy his leather jacket and dispose of his pomade.
His house was also filthy. If you know someone is coming to your house for the first time maybe consider wiping down the counters and chucking the old pizza boxes. While eating dinner he never once asks me anything about myself. He rambled on for at least an hour about his job as a customer service representative, repeatedly comparing it to my job as a 9-1-1 dispatcher.
Apparently they are pretty much the same job. He also kept telling me how much smarter and more attractive I was than his ex-girlfriend, who he repeatedly referred to as “the b-word ex.” He wants to go to a movie afterward but I honestly could not imagine sitting through an entire movie right next to this guy, and not just because he would not put down his stinky vaporizer.
I don’t want to hurt his feelings so I tell him that I think I may have some mild food poisoning and I needed to get him home so I could make a mad dash home. I realized that if I’d rather claim to have diarrhea then go to a movie with this guy it’s probably not going to lead to a second date. Within a minute of leaving his house, he starts texting me about how great our date was and grilling me to get a time for our next date.
I finally tell him that I think he is an awesome guy but our personalities don’t really mesh. He loses it and starts telling me that he’d never screw a fat, ugly girl like me and I should be grateful that he lowered himself enough to go out with me in the first place. Oh, and he hopes I die. I no longer felt bad about not wanting to go on a second date.
I haven’t been on a date since then. I’ve decided spinsterhood is more my jam.
15. Babe—Pig on a Date
I met a girl online, talked it up, and while she seemed a bit immature, thought heck, why not? She casually mentioned she really liked pigs. What she meant to say was she was obsessed with pigs. OBSESSED. We go to one of the best restaurants in the area for a first date—bad idea. Sometimes pictures are from someone 10 years prior, or the person hides things, etc. But that wasn’t the problem.
She looked just like her pictures. But I didn’t even have to have seen her first, because everything else gave it away. She came in a giant t-shirt that had a sparkly pink pig on it. Earrings? Pig earrings. Bracelets? Yep, pig bracelets. I swear her dad might have been Homer Simpson. She had this headband on with a little pig on it. Her shoes? Yep, pigs on the front of the toes!
But best of all, she had a GIANT—or at least it seemed giant—pink purse with the face of a pig on it. You could not stop seeing it once you did. And I’m sure everyone else in this nicer/classier restaurant saw it too. I felt overdressed with her but under-dressed with every other couple there. It was beyond embarrassing. For some reason, which I have to convince myself was politeness not stupidity, we still had dinner.
But it was the fastest damn dinner I’ve ever had at a sit-down place. I practically blurted out something about how “oh, you really do like pigs,” to which she started giggling—oinking?—and going on about how everything she has is pig-themed. Then she wouldn’t stop, and it became the dominant part of the conversation. There were a dozen other things that made it a trainwreck, but these were the clinchers to a solid zero out of five date.
I remember afterward commiserating with a friend of a friend, because I had to tell someone, and then I promptly buried this as my worst date.
16. What Could Have Been
He took me to the opera, except we never actually got there because, not knowing the area, we didn’t know exactly where it was or how to find it. Later I realized we actually were very close but the opera hall was surrounded by scaffolding, so we didn’t recognize it from the photos. Instead, we went to Pizza Hut. He spent the entire night talking about website design and computers.
It was sort of fine as I’m somewhat interested in those things, but he didn’t talk about anything else and, at points, seemed more like he was interrogating me. Afterward, he said we couldn’t go out together because I knew too much about computers. It wasn’t an unpleasant evening. It was just a bit strange.
17. What Are the Odds
Once I talked to a girl on Tinder and I hit it off with her pretty well, so we made plans to meet up later in the weekend. We’ll call her Sarah. The next day though, another girl that I talked to, that we’ll call Sophie, told me she’d be out at a bar close to me. She told me to come join her, and bring a friend. So I brought my roomie and went to meet Sophie.
As we got to the bar, I spotted Sophie sitting there with another girl, whose back was turned to me. I went up, gave Sophie a quick hug as I sat down next to her, and motioned for my buddy to sit on the other side with the other girl. It was only then that I actually looked at Sophie’s friend. After first noticing the intense stare I received from over the table, I made a disturbing realization.
Sophie’s friend was Sarah, the girl I had made plans to meet up with the following day. I could see she was equally taken aback as me, and for what felt like an eternity we sat there with the biggest deer-in-the-headlights-look before the silence was broken by Sophie saying, “Hey, this is my bestie, her name’s Sarah!” Which led to us nervously shaking hands and exchanging names, not knowing what else to do.
Already having shaken hands as strangers, neither of us really knew how to proceed, not wanting to mention the elephant in the room, since Sophie and my buddy had no clue what was going on. It actually did go all right in the end. My roomie and Sarah ended up talking and hitting it off. It seemed we’d reached a silent, yet mutual agreement not to mention the glowing mammoth in the room.
In the end, the girls actually ended up going back to our flat with us and spending the night. I told my roomie the reason I had looked so confused after they had left the following day. But yeah, that was such a strange date, which somehow worked out.
18. Fake It Till You Make It
I went on a date with a boy when I was about 16. Anyway, he was older. I lied about my age and even though I literally looked 11, he still believed me—super dumb of me, right? He was in his 20s. “Let’s get a drink, yeah?” Me being too nervous to tell the truth, I agreed. Flash forward and we’re outside of the bar. It’s our time to go inside and the bouncer checking ID asks me about mine.
“Uh, sorry, I must have left it at home”, I defensively exclaimed. He knew I was lying and I did too. My date looks at me weird and he starts interrogating me. I literally cracked with embarrassment. I started sobbing and at that point, I tried to run inside the bar like I actually had a chance. I even threw a tantrum causing a HUGE scene. Way to show my true age.
After, he looks at me with a blank expression and I honestly was crushed. We’re in the car leaving and at this point, it was nothing but silence until he was like, “Let’s go somewhere age-appropriate then.” “Age-appropriate?” I was shocked, as he wasn’t even mad at me. I didn’t know what to do with myself. I just sat in the back of the car, mentally beaten.
We drive for a while and I honestly thought I was going to get kidnapped. Then eventually, we pull up to a Chuck E. Cheese, and he leaves me there.
19. Home Cooked Meal
Well, this one time I took my date to dinner at—what seemed to be—a front for some type of illicit activity. We had just moved to a new area, and we wanted to check out the local shops and restaurants. While we were wandering, we stumbled into a tiny Italian place. Back home, the small hole-in-the-wall restaurants always have the best food, so we were excited to give it a shot.
Big curtains were covering the entry windows, so we had no idea what was inside until we trudged through the door. Inside, we were met with emptiness and silence. We both immediately thought the store was closed, and I spun around and searched for the store hours posted somewhere on the door. While I was looking, we heard a heavy THUD as a young woman barked, “I’ll be right with you!”
She appeared, greeted us confusingly, and asked us what she could do for us. Which, looking back is probably a red flag. But we were naive and hungry, so we said we were there for dinner. She looked puzzled but motioned us to follow her to a booth right by the entrance. She then disappeared into the back, and we heard a muffled conversation between our hostess and a man.
The consensus was basically they were not prepared for us or didn’t know how to proceed. I asked my date if she wanted to split, but she insisted we stay for the story. The square-shaped balding man burst through the kitchen door with two glasses of water for us, and in a very loud and deep voice, he explained that it was his birthday, and we would eat what he felt like making us. We whole-heartedly agreed.
We waited around 30 minutes, and he again returned with three large bowls of spaghetti and meat sauce. He placed two bowls in front of us, and one next to me for himself. He sat with us and ate. We had a light and awkward conversation with him during, and he kept asking us jokingly if we were cops or with the health board. He was incredibly nervous about us, so my date kept cracking corny puns or awful jokes because he would forcibly laugh at anything designed with humor.
We talked about our lives, the cities we’ve lived in, our pets—he had a teacup Chihuahua named Princess—and his wife. He decided we were good people and didn’t charge us for the meal. We wished him a happy birthday, he hugged us, and we went on our way. Easily the best spaghetti I’ve ever had in my life. The restaurant, unfortunately, no longer exists.
20. Babysitter for a Date
About eight months ago, I go on a Tinder date. She suggests brunch at Max’s Wine Dive on McKinney—we’re in Dallas. I pick her up at the Arpeggio apartments in Victory Park. She’s not ready, so she buzzes me in. Her apartment is beautiful—lots of high-dollar stuff, no roommate. We go to Max’s at 1 PM. She drinks an entire bottle of champagne by herself.
We leave, and in the car, she says she wants to stop by a shop in the West Village. I park in the parking garage and get out. I look for her and don’t see her. I hear a noise, so I look around my car and she’s squatting next to the wall peeing on the ground. We go into the shop. She takes a few dresses into the changing room and tells me to come over.
I stand outside the changing room and she pulls me inside. She completely undresses, gets in the clothes, asks me what I think, undresses, gets in more clothes, etc. She takes about $1,500 worth of clothes to the counter and tells the cashier she really has to pee. Cashier says sorry. My date begs, so cashier relents and takes her into the back, but it’s too late. The damage is done.
She also buys a new pair of pants. On the way back to her apartment, she answers a call and starts talking in a foreign language that I can’t place. Couldn’t even guess the continent. She’s very nervous and upset. She hangs up and tells me she has to go to her other apartment at the Cirque, also in Victory Park. She asks me to go in with her.
We go into her apartment, which is also completely beautiful and belongs only to her. She has a badass telescope that I start playing with. In the mirror, I see her open a safe and put something in her purse. She tells me we need to leave and asks me to take her to my house. We go to my house and she instantly passes out. She stays passed out for about six hours.
She wakes up and wants Dairy Queen. It’s closed and she starts crying. I take her to Sonic. She gets a cheeseburger, a chili dog, cheese fries, and a sundae. We go home, she eats it and throws up. She passes out on my couch. I read and go to sleep. The next morning, she asks if she can stay and watch football. I tell her I have plans and need to take her home.
She says she can’t go to either of her apartments. I tell her too bad, I have plans, and drop her off at Cirque. She texts asking when we could see each other again but I never respond.
21. Not the Best Start to Dating
This story isn’t as strange as some, but it’s my strangest. A guy I’d met a few times contacted me and asked me on a date. I had never been asked on a date before and accepted despite thinking he was a little strange and having heard some odd things about his family. He picked me up and everything seemed good. We decided to grab a pizza and eat it in a park.
When we went to purchase the pizza, it turned out he worked there, and he had all his co-workers come out to gawk at me. This guy wasn’t very popular with the ladies so he seemed to be proving he had a date. I’m bad in social situations and got super uncomfortable, but didn’t know how to bail and we went to the park. It was very awkward and I wanted to go home by the end of it.
We mostly just sat in awkward silence and tried not to hear each other chewing. I thought I was going home, but he decided he wanted to stop at his house. I agreed because I honestly did not know how to disagree—first dating experience. His home turned out to be his parent—we were both 18 to 20. This wouldn’t have been so bad if not all ten of his siblings—I don’t remember exactly how many siblings he had—and his parents were home and wanted to meet me.
They weren’t just a big, nice family, they were very religious and looked like they belonged to a cult. They all had long hair, homemade clothing, and they were all home-schooled. The mom said hello, then the dad came in and nobody was allowed to say a word while he questioned me on what me and his son had done on our date and when the family would be seeing me again.
It was terrifying. My date showed me his pet turtles, which were really cute, and finally drove me home. He tried to kiss me after making it clear he thought we were in a relationship after one date. At this point, I almost ran from the car. I messaged him later on explaining that I was only looking for friends at this point in time.
22. On the Lam
I got set up on a date with this pretty awkward guy. He picked me up in his car, which was sort of cool but oh my God he was a nervous driver. So nervous, in fact, that he accidentally ran a red light, lost his mind and ducked into a residential area to sit at the end of a cul-de-sac while freaking out thinking the cops were coming.
I tried to explain that if a cop had seen him we’d have already been pulled over but dude was too freaked out. I don’t even remember anything else about the date, just that. It was uneventful and I never really talked to him again because we had nothing in common.
23. The Other One
I had a good friend in university who disappeared overseas for a year after we graduated. I stayed there to study and teach, and one day I got a text from a number I didn’t recognize saying, “Hey, it’s Joe from business school, want to catch up for a coffee?” I hadn’t seen him in ages so I said yes very enthusiastically. I walked into the coffee shop at the right time, look around for Joe, and there’s Joe from business school—a different Joe from business school.
I couldn’t walk out because he’d already seen me, so we chatted politely for an hour and we haven’t talked since.
24. Not in on the Joke
I met this guy originally at a cocktail bar. We went to dinner on the first date, and then for the second date, we went to a comedy club. The first problem was he kept nudging me when I laughed, like I was embarrassing him. Of course, I was irritated by this but tried to tone it down since I still had two more hours to sit through.
Halfway through, he’s just acting really nervous and then the MC gets up on stage and says, “Welcome Brad to the stage.” The guy I am on a date with is not named Brad. It turns out that Brad is his stage name. He goes up on stage and proceeds to make two incredibly racist jokes. Tables turned. I was embarrassed and nervous for the rest of the show.
The joke was on me. We didn’t go out again.
25. Life Coach
I went on an OKC date once. The girl and I drove past a mattress and box spring hand wrapped in plastic. I drive a truck. She asked and then insisted that I stop and get the box spring. She wanted me to put it in my truck and then help her put it in her second-story walk-up apartment. I politely said no, I do not think that is a good idea.
I told her that there was a pretty solid chance of bed bugs, because sealing an item is what you try first when you have those nasty little things. She was having none of it. I refused. She started crying, telling me that I don’t know how it is to not have things and that it is easy for someone born with a “silver spoon in their mouth” to write off a free box spring.
She didn’t know me at all and made these assumptions based on who knows what. It was hard to hear since I came from absolutely nothing and worked my butt off to get to where I am. We pulled into the restaurant and she settled down a bit. We ordered our food. She answered a phone call at the table. It was a friend that had an extra ticket to a festival.
She really wanted to go but had just started a job serving food at a restaurant. I suggested that she not call her boss and ask for the days off. I worked in the restaurant industry when I was younger and I knew that her supervisor would not let her call off from her first weekend. She called her work anyway. She started crying when her boss said “no.”
I felt bad for her boss, not her. Her boss fired her on the spot. I paid the check with both of our meals still steaming and untouched. On the way back to her house we reached a stop sign. She jumped out of my truck and ran towards a trash pile. She came back with a hand-dyed glow painted end table and threw it in the back of my truck.
When I got to her house I said nothing. I just put it in park and hit the unlock button. She then took both of our to-go bags and ran off with her “new” end table.
26. Unknowingly a Criminal
Years ago, I met a girl online and after we’d approved of each other’s photos and list of interests, we talked on the phone and hit it off right away. She lived about an hour away, and she said she wanted to go to a local national park and go hiking and have a picnic. I get to her house to pick her up and see that she has packed a tent, sleeping bags, a cooler, and basically a full weekend worth of camping equipment.
I told her I thought we were just going hiking and she said, “I figured we could just camp out overnight. Just get me back home in time for church in the morning.” So we head out, we set up the tent, go for a hike, swim in the lake, have dinner in the lodge, head back to the campsite, make a fire, and settle in for the night. Later, in the tent, stuff starts happening.
After a while she says, “can we wait a bit on that, and just go to sleep.” I oblige and we sleep. In the early morning hours, she wakes me up by making it very clear the wait is over. After we finish, she starts crying. She apologizes and says she’s not ready to be in a relationship. I tell her I understand but I’m pretty confused by this point.
We pack up everything and I drive her home and drop her off at her house. About 15 minutes later, I get a call on my cell phone. It’s my dad. He asks, “what the hell are you doing?” I tell him I have no idea what he’s talking about. He says, “the Sheriff’s department just came by here looking for you and asking if I knew your whereabouts. You’re wanted in the disappearance of some girl. Her family said she never came home last night. They went to your place first but nobody was there.”
Apparently, she wasn’t home for church and her family freaked out. I called her and told her to please contact the Sheriff and let them know she was not, in fact, kidnapped. She laughed and then called them. We never had a second date.
27. Should’ve Seen That Coming
In 2001, internet dating hadn’t really taken off yet, so this happened as a result of a personal ad. I was newly single and feeling pretty frisky, so I took a chance on a “Mr. Wrong, 24, seeks Miss Right” ad. We corresponded and spoke on the phone before meeting, and everything sounded okay. I was misled quite badly. Paul was more like 48 than 24—a paunchy, pasty, bargain-basement Freddie Mercury lookalike.
Being of Italian heritage, he was staunchly anti-racist but thought homophobia was fine. He got drunk and wanted to take me to the circus. It was a really uncomfortable experience but I managed to escape with just one cheek having been slobbered on after he slurred, “You’re really cute.”
28. Off to a Bad Start
I met a girl online and decided that we should meet for a date. I’m female by the way, so this sort of matters. I arrived in a strange town that I didn’t know so I relied on her to show me around. She took me to a youth LGBT group. I thought we were staying but didn’t mind. It’s a bit odd but I was newly “out”. Turns out, it was just a chance for this girl to show off that she did, in fact, have a date—they didn’t believe her apparently—and I existed.
It was really awkward. When the youth group leader came in, she stood up, grabbed my hand and said “later jerks” and we walked out. We went to a bar for a drink, and then on for some food. It wasn’t going well, she was very odd, but I was new to all this, and in a town I didn’t know. Once we’d eaten she said, “Oh I just need to see a mate who’s staying at XYZ hotel”.
Fine. We went to see this friend. Oh no. She’d booked a hotel room for us for the night! Yeah, I left pretty quickly after that. I may have been inexperienced, but I wasn’t about to be tricked into a night in a rough hotel with an odd little lesbian. No thank you.
29. In It for the Food
I meet a guy online. He asks me to dinner at a tapas place. I agree because I’m bored and he seems nice enough. We’d been texting for a couple of weeks and it seemed chill. I get there and he’s late to meet me. He looks nothing like his profile—about 100 lbs. heavier, bad skin, and is just dressed really sloppily—but I told myself not to be shallow.
We are looking over the menu—which was fantastic by the way—and I suggest a few things I’d like to eat and he begins saying he doesn’t eat sweet potatoes, aioli, capers, salmon, radish, arugula, kale, balsamic vinegar, etc., basically all ingredients except for bread, meat, and cheese, and that he won’t eat any food if that’s what I order.
I tell him to get what he wants then and I’ll get something for myself. We get our food and he is the messiest eater I’ve seen in my life, getting crumbs and food bits all over his shirt and the whole table and it was just painful to watch. He also kept insisting I try his food, but I’m pescatarian and lactose-intolerant so I declined, at which point he began berating me and my food choices and being for a “picky eater.”
They clear our table for dessert and he then gets down on one knee and tries to give me a promise ring because he “felt a special bond with me and wanted to pledge his life to me” after having met online a few weeks before. Yeah, no thanks. Politely as I could, I declined, to which he started calling me expletives in the middle of the restaurant and then ugly crying and storming out.
So I had to pay for the terrible date HE asked ME on because I didn’t want to accept a pre-engagement ring.
30. Let It Go
It’s 2001, so it’s VHS & chill at this girl’s dorm room. It’s my first time over there, and there is this giant bear on the bed. Like, got the softball in the milk jug at the carnival first try tier bear. It occupies 50% of the surface area. I say, “Whoa, how’d you score that bear?” She says that she doesn’t know. I reply, “really?” She still says that she doesn’t know.
A few minutes go by. I just can’t let it go. So I ask “you really don’t know?” She insists that she doesn’t. I say, “Okay, look. It’s okay if it’s from an ex. I don’t care if you stole it. I’ll believe almost anything you tell me at this point. But there is no way in hell you’re going to tell me you don’t know where that giant bear is from. I had a stuffed dinosaur a quarter that size that I got when I was six and I could tell you every detail about how I got it.”
She replies: “Well good for you. But I don’t know how I got it. Are you going to be able to let this go?” I look at the bear and the bear stares back with eyes full of secrets. I said, “I don’t think I can,” and I walked out.
31. Like a Race Horse
I started talking to a girl I came across on a dating site. We made plans to meet about one week after we began talking. I ended up canceling the plan’s a few hours before we were supposed to meet, as I had something come up. I told her I was available the following day, as we do not live in the same city. A few hours later she responded and asked me if I wanted to take a road trip to another city a few hours west from where I’m located.
She just wanted a co-pilot to keep her company. I agreed, although partially because I felt bad for changing plans at the last minute the previous day. I was skeptical, as I’ve never just taken a random road trip with some girl that I haven’t met before. She picks me up in the morning. It’s not too awkward at first, easy conversation for the most part.
Within 10 minutes of being on the road, she needs to pee but can’t wait for the next gas station. She abruptly pulls over on the side of the highway and does her business. OK, I’m thinking whatever, you gotta go, you gotta go, right? The place we were traveling to was about 200 km from where I lived. Let’s just say we had to make another five stops, two more on the highway and three at gas stations before we arrived at our destination.
Yes, I started to count after the third stop. Anyways, I’m definitely thinking this girl has some kind of STD or issues. That’s a lot of pee breaks in such a short amount of time. Okay, so I was told she needed to pick a few things up in the city. However, it wasn’t just things—it was her 74-year-old grandmother! Whom I would shortly be meeting for lunch, along with a few other members of her family.
I said to her, “What the heck? You’re kidding, right?” Well, she wasn’t. For heaven’s sake, at this point I did not have much of a choice, considering she was my ride back home. Long story short, it was awkward as heck. It was her aunt, a cousin and some family friends with her grandma.
It was like a family reunion. I felt like I was in some kind of dark comedy show, and I had to improvise nonsense. Anyways, we made it back home after four more pee breaks, and having to pretend and lie to her grandmother about actually knowing anything about this girl. Yeah, I didn’t talk to her again. How is that for awkward?
32. That’s a Bold Move
I went out with a customer from my work. I was a bartender, so I got hit on quite a bit, but this was the first time I’d actually gone out with someone. He took me to a bar near his apartment. The place was a real dive and a little too hipster for my taste, but whatever. We were having a great time talking and enjoying some drinks, when I suddenly notice the TVs behind the bar.
Instead of playing sports or the news or something, they’re playing old dirty movies. I brought it to his attention, and he kind of just shrugged it off and said it was normal for this place. I actually thought it was pretty cool and this joint became one of my favorite bars—more for the cheap alcohol than the “entertainment”—but it was still a really strange place to bring someone on a first date.
33. Three up, Three Down
I have had three separate dates with three separate women that all turned out to either be Christian revival meetings or Young Life. C’mon.
34. In the Line of Fire
Michael Che—comedian and anchor for Saturday Night Live Weekend Update—ruined one of my first dates! I go to a lot of standup around NYC and I happened to see him trying out material at two different free shows in the same week. He was doing this crowd material bit about dirty videos where he would pick a guy in the front row and corner them and ask them what they searched for when they looked for them.
The first time I saw him doing it he just would not let up on this poor guy. The guy didn’t want to answer and kept saying, “I don’t know” or “I’m not sure” but Che kept asking, “come on, man, I KNOW you know. What do you mean you don’t know?” The guy never relented and said anything out loud but Che kept pressing him for seriously the entire show, like he kept going back to this one poor guy.
Cut to later in the week, and I’m taking an OkCupid date to a standup show. I sit in the front and Michael Che turns out to be the surprise headliner. The second I see him on stage I just know it’s gonna be me. I know he’s gonna do the bit again and I’m sitting front and center. My brain is racing trying to think of a good way to get out of this awkward situation.
This was a very casual date and I had not been speaking to this poor girl for very long plus I’m already a weirdo. Within like 30 seconds he turns to me and asks, “what about you, sir, what do you type in the search bar when you look for you-know-what?” And I think, “okay self, just say the most innocuous harmless kink possible.”
I stall for a second with a “who me?” and he repeats the question, so I blurt out without thinking, “Redheads!” Whew, fine, I’m in the clear. Awkward situation handled. I forgot that my date was a redhead. Of course, he immediately picks up on that, saying “You know the girl sitting next to you is a redhead right?” and I reply, “yes, we are…actually…here on a date.”
He goes on to say, “Wow, this has actually never happened to me during this bit before.” Then he cut me some slack and moved on. In the larger scheme of things, this probably wasn’t that bad, and the date wasn’t going spectacularly anyway so it wasn’t like a huge loss, but it definitely made things very awkward for the rest of the evening.
It was kind of a relief when she said no to a second date because then I immediately texted her back and was like, “That’s fine OH MY GOD CAN WE TALK ABOUT HOW CRAZY AWKWARD THAT WAS?” and she was like, “I KNOW!!”
35. Learn Something New Every Date
This was a second date with someone I met on Tinder. The first date had been the typical meet up for drinks at the local bar. We stayed a couple of hours and had chemistry, made out a little on the walk afterward but we both had 6 AM alarms the next day and went to our separate apartments. For the second date, she invited me to the taxidermy museum in Gowanus.
I’ve just discovered now that this place closed recently, but its motto was “exploring the intersections of death, beauty, and that which falls between the cracks.” This is, for lack of a better word, a hipster-capitalist museum that is really just a gift shop. There are lots of dead things for sale, stuffed, bones, jarred, etc.
Lots of things outside my price range, but there’s also a basement which, I suspect, retains the climate control system original to the building, which is to say that when filled with 30 to 40 warm bodies on this cold, winter evening, the temperature was actually pleasant but the humidity was about 250%, making it feel like the image of a dank dungeon.
The occasion was a lecture being given in the basement by a traveling professor, on the subject of sex work in France in the interwar period. It mainly consisted of a slideshow with compromising pictures of some particular French sex workers. It was very informative and memorable.
36. Can’t Top That
On a first date with a girl from the Internet. We had never met her before, so we got coffee in what was usually a busy-ish cafe. The coffee shop was empty except for us and one guy sitting alone at the table right next to us, looking like he was both incredibly nervous and about to cry. We get our coffees and start in on the getting-to-know-you conversation.
That’s when another guy shows up with a bag and sits down with the first guy. The second guy looks equally nervous and equally close to tears. We try to continue conversing, but their conversation is so compelling that we kind of give up and start eavesdropping. The first guy says, “Thanks for coming. You didn’t have to meet me, I wouldn’t have blamed you.”
The second guy replies “It was the right thing to do.” He hands the bag to the other guy. “Pretty sure that’s all of it.” The first guy says, “I don’t need or want any of this back. I’m never going to look at it again.” The second guy asks, “You think I want it around?” The first guy replies, “No, it’s just…I know it’s not fair of me to say this, but it hurts. I miss you.”
Quietly, the second guy says, “I miss you too.” Now louder and more confidently, “But I can’t do this anymore.” He takes the first guy’s hands on the table and looks deep into his eyes, “I’m so sorry. I’ll never stop being sorry.” The first guy looks back with eyes full of longing, continuing “I want to believe you. We had a really great thing going.”
The second guy places his hand gently on the first guy’s cheek, saying “It can be great again. I’ll do anything for another chance. Anything.” These two guys went from a breakup to the most epic, tearful, emotional reunion either of us had ever seen, right next to us. By the end, they were making out and cuddling and crying, while us and the barista just kind of stared at them in silence.
To say that it sort of overshadowed our date would be an understatement.
37. So Much for the Double Entendre
Oh, I have one for this! I met this girl at a social thing on campus one time. She was cute and weird and seemed cool and she was talking about her art and stuff, and I was all like, “I like art,” because I actually like boobs and she had two of them, which I find is the optimal number. So, she invited me back to her place to check out her art and do some “finger painting.”
So, I drive her back to her apartment and she tells me to park anywhere because there are no assigned spots. Cool. So we go inside and she’s showing me her stuff and she pulls out the paint. It turns out finger painting was literal and not a euphemism, but I am not deterred. So, we’re painting and flirting in her bedroom.
I playfully put paint on her nose, and she returns the favor. Everything is going great. The phone rings, and she has paint on her hands, so I pick it up and say hello. On the other end of the line, a guy says, “Who the hell is this?” “Uh, this is [my name]. Who is this?” “This is her boyfriend. Put her on the phone.” So, I hand her the phone and she doesn’t even blink.
She’s all smiles and I hear her say, “Yeah we’re over here painting. You should come hang out!” She hangs up the phone and my jaw is on the floor. She’s all like, “Oh, that was my friend Mike. He’s going to come hang out with us!” I look my phone, “Oh wow, it’s already 1 AM. I didn’t realize the time.” So, I make my excuses and nope out of there. I walk out to my car, and it isn’t there.
I walk back to her apartment and knock on the door. It turns out that they tow cars without passes starting at midnight, and we were having so much fun she lost track of time and didn’t realize it was that late. She also didn’t have a car, so she couldn’t take me to the tow place. So, I get to wait for her boyfriend to show up.
She introduces us, explains the situation, and then he drives me to the tow place—just the two of us. We drive in the most complete awkward silence I’ve ever experienced. I swear he didn’t even put on the radio. When we get to the tow place, the only guy working is out on a tow, so I have to wait again. He turns to look at me for the first time and says, “Do I need to wait?”
The tow place looked like the kind of spot people get murdered at, but I decided that was preferable to another awkward minute alone with this guy, so I bid him adieu. The tow guy showed up 20 minutes later. I paid $60 to get my car out of impound and learned a valuable lesson.
38. They Must Be up to Something
When I was in high school, a college guy asked me out. We both didn’t know what to do after dinner, so we drove around the neighborhood in his uncle’s sports car just talking. Then, the cops pulled us over because there were three calls of a car just driving around and around.
39. One-Sided Dine and Dash
Unfortunately, I have a kryptonite-level weakness for redheads. This is back in the prehistoric era known as the mid-1990s when I was 19. I met a cute redhead at a party and instantly asked her out. So, we go out to dinner, her pick, and she chooses this cheap casual restaurant. I’m like what the heck? But hey, super cheap date.
The entire time we are there it is nothing but silence, although she orders a huge meal and I’m thinking she has the metabolism of a racehorse in order to be that skinny and eat so much food. Our meal shows up and she goes down on the pot roast like a savage and in between bites she regales me with how she lost her job and is living in a rundown house that has a leaky roof, the powers been turned off, and she and her LESBIAN girlfriend have been starving—her emphasis not mine.
With that revelation, I’m struck speechless and don’t really know what to do. She has her leftovers boxed up—plenty for her girlfriend—and dashes before the bill is even presented to me. At least we were too young to drink. Some friends confirmed her story and I was the butt of some jokes for a while. Even at the time, I found the whole thing surreal and hilarious.
40. Can’t Catch a Break
I had three doozies in a row. The first seemed pretty decent and if he had just stuck with beer he probably would have been fine. But, I’m a whiskey drinker and he opted to join me. He got wasted and confessed he was looking for an older woman to take care of him financially, shouted and slurred in my ear that he was a very sensual lover—much to the amusement of the people next to us—and desperate to have children very soon. Weird.
The second guy took me to this party and he sort of ditched me with a group of his friends. Luckily, they were all very nice and all polyamorous. I learned quite a bit about their lifestyles, which was interesting. However, every time I glanced up, he was watching me intently, but like hiding behind posts and creeping around corners.
When I finally approached him to say goodnight after having had zero interaction with him, he launched into this thing about needing to be sure I would be down with his lifestyle. He was just odd, that one. The last one, unfortunately, got fired that day and really should have canceled. When he found out my job was sucking the corporate American teat all the way to the bank, he just lost his mind.
I mean, I would have been insulted, but it was also amazing to see someone completely break with all social norms and just spew every insecurity for the whole pub to witness. I paid his tab and scooted out of there. I felt really bad for that guy.
41. The Great Shoe Heist
We had a great date that ended with a walk on the beach. I took my shoes off and he offered to hold them while I grabbed a couple of seashells. We walked back and while I’m washing my feet off he walked over to his car. I thought he was going to grab a towel but instead, he took off with my shoes!
42. Groundhog Date
It was my second date with this guy and he said the exact same things that he said on the first date—word for word. The same stories, the same “random thoughts,” the same questions. It freaked me out so much that at first I played along and answered in the exact same way, as though we were both following some weird script.
Eventually, I tried to break the mold and ask him new things, but he would just bring it back around to the same topics as last time. It was like I was in a computer program and there was a glitch. It still freaks me out to think about it.
43. Dark Date
I met a guy at the skate park when I was 14. He asked if I’d go out with him the next day. I thought he was gorgeous, and when he said I should dress up I expected something special. The next day I showed up, and I couldn’t believe my eyes. He took me to his little sister’s funeral.
44. 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.