Dating can be a terrible way to spend your free time when you really think about it. Fireworks, romance, and great first kisses are the payoff for putting in the difficult work of finding that person, but until then, it can be a total waste.
Date Night Robbery
“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 had 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 I just left her to walk home alone.”
Date Night Crime Scene
“Met this girl online, and the way the conversations went it was always friendly, getting-to-know-you type banter. After a few online conversations, we meet up at a bar by her. The plans for the evening were to go out and then return to play Donkey Kong Country at her place. Being the oblivious male I am, I genuinely was excited to play some DKC on Super Nintendo.
We meet up at the bar and things go fine. I wasn’t really attracted to her at all, but she was nice and we had an alright time at the bar. So we get back to her place and start watching TV. I look around and don’t see a Super Nintendo. Thought maybe it was in her bedroom. I don’t mention it because I don’t want to be rude. We’re watching more television when all of a sudden she looks at me with murder in her eyes. ‘Are we going to stop playing games?!’ she asks.
I look at her, smiling, trying to play it off. ‘Do you mean Donkey Kong Country?’ She really didn’t appreciate that. She scoffs and then proceeds to chide me about how guys are always wanting to play games and only want action. I told her the only game I was wanting to play was DKC. This is when it got weird. She gets up off the couch, calmly, walks to the kitchen and pulls a butcher knife out of somewhere. She just stands in the kitchen, still with the look of murder in her eyes, and stares me down. She doesn’t move at all, just staring with the butcher knife at her side. I look back for what feels like a few minutes, and then I jump up and dash for the front door.
I didn’t even bother closing the door, behind me I hear the door slam hard, and she’s shouting and swearing at me at the top of her lungs as I escape. A night of what I was hoping to be relaxing friendly conversation and Donkey Kong Country turned into my ‘maybe I could have been murdered’ dating story.”
Take A Seat, Seriously
“I met him on OKCupid. He was hot, funny, and seemed to be the holy grail of internet dates – kind of a bad boy, but had his stuff together. He rode a motorcycle but owned a business. So yeah, I was pretty excited about him.
Since I had actually started to like him, I decided to hold off on kissing him or getting physical for a bit. We had two great dates, one of them a scenic ride through the forest on his motorcycle after a meal filled with jokes, banter and flirting – things were looking pretty good. The only slightly weird thing about him is that he wouldn’t tell me his last name. No biggie, I thought, maybe he’s had bad luck with internet dates?
Third date, a warehouse party with board games. Started to tease him about his mystery last name, making up reasons that explained why he wouldn’t tell me, you know, former stalkers, he was heir to a fortune he didn’t want me to know about, etc. He cuts off my jokes by saying, ‘We have to talk.’ Uh-oh!
We move over to a beanbag for two in the warehouse away from the games. He started the conversation by saying, ‘You know that show Dateline?’ to which I replied, ‘Yeah, I guess?’ I hadn’t owned a television in years back then. ‘Well, I was kinda on that show.’ Ohhhkaaay, still not getting it.
‘Yeah, I met Chris Hanson.’
I’m still clueless, so he has to spell it out. Basically, it’s a show called ‘To Catch a Predator,’ and it’s a sting operation to catch pedophiles. Turns out he’d been chatting online with a girl who was supposedly 13 but was really an 18-year-old actress who looked super young. He chats with the young’un a few times and decides to drive his motorcycle a half hour away to visit her. Only the visit didn’t go as he planned, as while she was getting him a glass of lemonade, Chris Hanson popped out, revealing the camera crew and informing him he was busted.
The guy was arrested, had to register as an offender, and a few years later began trying to go on internet dates without revealing his last name. It’s a distinctive last name, so when you search his full name, the show comes up. It was quite a shock to Google him after the date and watch the segment.
I respected him for telling me and owning up to it, but yeah, we never spoke again – holy grail not found.”
Catfish, Catfish, Catfish
“So, a few years back I lost a bet with a friend. The loser had to go on ten Craigslist dates. The rules were as follows: I had to post a personal ad in the women seeking men section. The ad had to be simple. I had to correspond with the people who responded and if they asked me out on a date, I could not refuse. Repeat until reaching ten people. Once the ten was met, I was off the hook.
I don’t remember the exact wording of the personal ad, but it said something along the lines of ‘young, professional woman seeking young professional man for light conversation and friendship.’
Enter the crazy.
My first date was with a man who responded within two minutes of the ad being posted – yikes. He responded saying he had just moved to the area, was 29, and worked as a lawyer. He too was looking for friendship and to meet people in the area. We exchanged emails back and forth, and in the third or fourth email, he asked if I would like to meet for coffee. According to the rules, I had to accept. So I set the meet up with him at my local coffee bar. I asked to exchange pics so we knew what we looked like, but he evaded and instead described his clothing. Red flag.
I went to the meet up accompanied by a close guy friend who works as a bouncer. He sat a few tables away for support and in case things got crazy. I drank my coffee and waited. I told him I would be wearing a red cardigan and he said he would be wearing a blue button down. Before I knew it, an older gentleman—late fifties, early sixties—sat down at my table asking me if I was the girl from the Craigslist ad. I confirmed I was and he introduced himself as the man I was supposed to meet.
I immediately called him out on lying about his age, to which he replied, ‘Well in my head and in my heart, I’m 29, so what’s the difference?’ Yeah, no. He then continued on to admit he was not a lawyer and that he was a retired sanitation worker. I asked him why so many lies? His response: ‘I always wanted to be a lawyer and you said you wanted a professional, so I figured it was a good match.’ He started getting upset that I was asking him so many questions and that I was implying that he was a liar.
At that point, I asked him straight up about his expectations. What did he think would happen when I met him and realized he lied about everything he’d told me? He responded, ‘We had so much in common, I just thought you were already in love with me and you wouldn’t care.’ I was speechless. I didn’t even want to know how he had the idea I was in love with him. I was starting to get super uncomfortable.
I looked over to my friend and implored him to save me, but he didn’t notice my distress at first. The gentlemen saw my distress and smiled while he asked me ‘Are you uncomfortable?’ He started leaning over the table as if to grab my hand, but instead grabbed my coffee and started chugging it while making direct eye contact with me. I sat there stunned and unsure of how to react. I looked over at my friend again, and thank god he saw my look that time. He immediately came over and pretended to be a friend who happened to be at the cafe.
I stood up to greet him, and after a moment of chatting, made an excuse to use the bathroom. My friend caught the drift, and as I went to the bathroom, I booked it out first and he quickly followed.
Thus ended my first Craigslist date in all its weird and uncomfortable glory.”
Not The Best Of Both Worlds
“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, and I’m a guy. She insisted that we were still friends, 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, 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!’ or ‘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 everything 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, 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’s car. 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″ 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 say ‘Oh, we have a mutual friend!’ and hope Ross doesn’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. 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 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.”
Parking Boot Beginnings
“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 would be able to use his dad’s car, but now he can’t.
So I go to 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 assaulting you or something.’ I asked him what in the world he was talking about. He just kept rocking in his seat anxiously, worried that he would be accused of taking advantage of me.
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.”
He Thought He Had Game, But No
“Met a guy online, of course, and after talking for a couple 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, no?
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 911 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 plenty of vulgar words.
He wanted to go to a movie afterward, but I honestly could not imagine sitting through an entire movie right next to this guy. 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 back to my place. 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, grilling me to get a time figured out 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 date a fat, ugly woman 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.”
Italian With A Side Of Detective Work
“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 wholeheartedly agreed. We waited around thirty 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 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.”
Babysitting Your Date
“About eight months ago, I set up a Tinder date. She suggests brunch, so I pick her up from her apartment. She’s not ready, so she buzzes me in. Her apartment is beautiful, lots of high-dollar stuff, no roommate.
We go to the restaurant at 1 pm. Eventually, we leave, and in the car, she says she wants to stop by a shop in 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. Eventually, she takes about $1,500 worth of clothes to the counter and tells the cashier she really has to pee. The cashier says sorry, no. 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. She asks me to go in with her. We go into her other apartment, which is also completely beautiful and belongs only to her. She has an incredibly awesome 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. Stays passed out for about six hours. Wakes up, 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 come home, she eats it and throws up, passes out on my couch. I read and go to sleep.
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. She texted asking when we could see each other again, but I never responded.”
Cadavers And Butterflies
“I briefly dated my anatomy lab partner in college. Our first date was definitely strange. He was Australian.
We’d been talking in class and totally hitting it off, and he asked if he could take me out to dinner after working in the lab together the next day. So the next day, we meet at the cadaver lab and study the small and large intestines of dead bodies for a couple hours, taking notes and doing sketches while chatting – ya know, how most dates start.
Then we washed up and walked out to the parking lot together, where he opens the door of a shiny new Jeep for me. He’s from a very well-off family, so I assume they just bought him the car for school while he’s in the States. But as he’s pulling out of the parking lot, he tells me that the Jeep belongs to his roommate, who let him borrow it for this date. He confesses to me that this is actually the first time he has driven in the States. We both laugh a little. I’m just stoked to be there with this fascinating, hot, foreign guy who loves anatomy as much as I do.
Then he blows through a stop sign and almost gets us T-boned. Then he accidentally drives a couple blocks on the left side of the road. Then he tries to make a left turn from the far right lane at an intersection, almost getting us hit again. He keeps nervously laughing off all these close calls. I offer to drive, but we’re almost to the restaurant at this point and he says he’s got it.
We somehow get to the restaurant in one piece. It’s a steak place. It’s pretty good. He asks me all about my life. I try to ask him about his, and about his home country, but he doesn’t have much to say about it. Seems like he just wants to hear me talk instead, but was very sweet regardless.
Then came the drive back home. He just needed to get me back to the school where my car was but was very concerned about the gas light being on in his friend’s car. He pulled into a gas station, where he then struggled with the gas pump for about 15 minutes. Trying to figure out how it worked, what to select, whatever – too embarrassed to ask for help. Finally, he disappeared inside the store and had the cashier come out and help him put gas in.
He got back in the car and looked sad all of the sudden. I asked what was wrong and he said, ‘Well, I know it’s late, but I don’t want to take you home yet. Can we go one more place first?’ I said sure, as long as it was close by, as I didn’t want to die a fiery death tonight. He pulled into a park a couple blocks away. I thought ‘Oh, classic, we’re gonna make out at a park at 9:30 pm like eighth graders.’
Nope. He goes, ‘One sec!’ and gets out of the car, runs back to the trunk, and pulls out a set of golf clubs. I get out of the car and he explains, ‘We went golfing yesterday and my clubs are still in here! Do you golf?’
‘Nope, not once in my life, actually,’ I reply. ‘Well then, it’s your lucky night,’ he said.
He then proceeded to teach me how to swing a golf club. In the dark. Standing behind me with his arms around me, holding my hands on the club while helping me swing, all of that good stuff. I hit a couple and quite enjoyed it. Then he looked around like he was looking for something and pointed and said, ‘Make me a deal. If I can hit that tree with a golf ball from here in one try, you have to kiss me.’
I agreed, the tree was about a football field away. He swung. I realized you can’t see a golf ball 100 yards away in the dark. He says, ‘Did I hit it?’
‘I don’t know,’ I begin. ‘I can’t te—‘
And then he kissed me. Like, perfectly. Like, not-too-much, not-too-little, just totally nailed it. Cue butterflies. Then he said, ‘Okay, I guess I have to get you back now, huh?’ We got back in the car and started heading back. We pulled into the parking lot by the lab. My car was the only one left in the lot. He hit it with the Jeep trying to pull up next to it. I wasn’t even mad.
But I drove for every subsequent date.”
Party Hopping Isn’t Much Of A Party
“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. 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!
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.
Arrive at the third party. As soon as we walk in the door, Tim says he needs smokes, and the girl and Tim run out 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, 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 go to bed 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 approaches me, so I stay for another hour and laugh it off with the people at the party. I’m still friends with some of those fine people today.”
Perfectly Strange First Date
“I met this guy when I was in college in D.C. and he invited me for a trip on his motorcycle to visit 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 ignored 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, 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, which was really a two-room cottage, got my boot off, and 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.’
Suddenly, I’m thinking, ‘Pickle jars.’
He rides to the local grocery store to pick up some food because there’s nothing in the house. He comes back with groceries. ‘Guess what’s for dinner?’ he asked. ‘Chicken Kiev,’ I answered. It was the most unlikely thing I could think of at the time, but 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.”
Interview With The Parents
“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 him 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 had all his co-workers come out to gawk at me. This guy wasn’t very popular with the ladies and seemed to be proving that he actually had landed 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 agree because I honestly did not know how to disagree – first dating experience. His home turned out to be with his parents. His parents were home and wanted to meet me.
They weren’t just a big, nice family, either, they were very religious and looked like they belonged to a cult. They all had long hair, homemade clothing, they were homeschooled. 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.”