In the era of online dating, we have become accustomed to horror stories of catfishes and frauds. It’s all too common for folks to use an outdated picture, or edited photos, or worse yet—someone else’s picture as their profile picture for their online dating profiles. These hurdles aside, there is something even more unnerving when a person seems to be attractive, hygienic, and charming—but is hiding something underneath the surface. A date can be going splendidly until the fateful moment in which they reveal something about themselves that is a huge red flag. Get ready to abandon ship, as we plunge into these stories from people who discovered the dark doings of their seemingly docile dates.
1. Close Calls
I had a great date with a girl I met on a dating site and I was walking her home at the end of the night. All of a sudden, she started to run. I started to chase after her and when I caught up, I asked her what happened. She just said, “Police! I have a warrant out for me.” I said forget this and left, but went in a different direction than she went—but the story didn’t there.
While I was walking home, the cops pulled up and started asking questions because they’d seen me with her. I had to spend a good 20 minutes explaining the situation to them and how I was in no way involved in her criminal activity.
2. The Witch
I was sitting at a bar on a date, when out of nowhere my date informs me that she is a witch and that she had made her last boyfriend love her by casting a spell on him. She was even nice enough to tell me how the spell “worked.” She took a vial of her period blood and poured it into his wine, and tricked him into drinking it. As she said, “Now he’s mine forever.”
She went on to say that it turned out she didn’t really love him, but because of her spell, he would love her forever. She claimed he was still desperately in love with her even though she had dumped him. Yikes.
3. The Second Date
I got invited to a party as a second date. The girl met me at the door and walked me to where the band was playing, she then walked away with some guy. I didn’t see her for a good hour before I decided to leave. Turns out he had some “party favors” and she slept with him to score some. I guess he ended up being the one to do me a favor.
4. A Commonality
My friend in college set me up with this nice young woman because he thought we had something in common and would hit it off. Our entire conversation that night at dinner went something like this. I ask, “So, how did you meet John?” She replied with one word: “School.” I go on to ask, “Did you have a class together or did you live in the same building or something else?”
She says: “Same apartment.” Me: “I see. So, what do you do when you’re not in class or studying?” She replies: “Television. Music.” Me: “Did you want to do something tonight besides eat and talk?” She said no. After the date, I asked John what made him think that she would be a good match for me. He said, “Well, you’re Japanese(-American) and she’s Japanese (exchange student), so I naturally thought you two would get along.” Sigh.
5. The Sister
I went on a date with my buddy’s sister. I hadn’t seen her since we were kids, but by the time this happened, we were both in our 20s. She randomly started chatting with me online one day out of the blue. We talked a lot pretty much every day for a couple of weeks and really hit it off. So, we decided to get together to go to a movie.
Only, when I got there, I couldn’t pry more than two words out of her at a time. She only said “yes/no” and other one to two-word answers for very open-ended questions. I’m decent at keeping a conversation going, but I can’t do it all myself. I took her home, dropped her off, gave her a hug, said hi to her mom, then never really spoke to her again. Later, I found out the truth.
She was really into me and was just nervous. What a shame. Last I heard, she lives alone with her dog and is dating some dude out of state that is 25+ years her senior.
6. The Historian
I went out with a guy who, while we were walking downtown, would stop at every building and give me the historical background of each building. This isn’t a bad thing—the weird part was that he did each one in a different accent. Oh, but it gets worse. When it came time to cross the street, he did some ballet leaps all the way across.
He also asked me about all of my classes and knew details about them, when I had never told him which classes I was taking.
7. Islam, the Country
My worst date was with a girl who thought that Islam was a country that she could visit. Her head was so full of air that when we left the restaurant and she invited me back to her place, I started to make excuses why I couldn’t stay. She was so persistent that in the end that I lied and said that I was a very strict Christian and that I thought that it’d be inappropriate to go back to her place.
8. The Garbage Bag
My dad had been set up on a blind date by his friend. As he picked up his date, he noticed she was carrying a strange bag, not a purse or anything normally brought on a date, but a garbage bag with stuff in it. He kind of shrugged it off, and they got in the car and started driving. During the car ride though, he noticed what was contained within those bags and his blood ran cold.
It was two baby dolls with blood smeared on them. He asked her why she had brought two dolls, and she just nonchalantly responded, “They’re my children.” My dad instantly felt that this girl had some problems, so he stopped at a gas station and asked her to go inside to get him cigarettes. He immediately drove off, abandoning her at the station with her two bloodied dolls.
When he talked again with his friend who had set up the date, his friend said, “Oh yeah, I forgot to mention. She had two abortions in the past two years, so now she carries around those dolls and claims they’re her children. I thought it was no big deal.”
9. A German Girl
A number of years ago, I met this German girl at the bar I bounced at. She was kind of cute, really smart, and knew more about music than almost anyone I’ve ever met. She says that we should hang out sometime, so I mention this jazz bar that has an amazing open mic night on my night off. She says yes, and we make plans.
We meet at the appropriate time at an open mic night at another place, but she barely talks to me the entire time. Neither of us drives a vehicle, so we jump a bus to a nearby restaurant to eat. Then she mentions a piano bar so we jump a cab over there. All this time, she is talking about her roommate and how she is worried that he doesn’t have health insurance.
That’s just a little strange until she talks about how she was discussing that situation with his mother. Warning bell kicks on hardcore. Turns out that her roommate is actually her fiancée and she believes that she is pregnant. She hadn’t been to the doctor, but “a woman knows these things.” So, we get to the jazz bar and I get drunk off my butt because I know this isn’t going anywhere.
The music, as always, is great, but since we’re both taking public transit, we have a different problem: the buses have stopped running. So, she ends up calling her fiancée to pick us up. As fate would have it, I have a good friend who lives pretty close to them, so I was able to go over there and get away from them. Yikes.
10. Boring Guy, Fast Car
I was on a second date with a guy I met on the internet. Boring guy, fast car. He decides to evade the police while driving 120mph on the highway and takes an exit too fast. That’s how I ended up in an upside-down 350Z—which had rolled over at 90mph into a stone wall and into a telephone pole. Over a year of physical therapy. Minor nerve damage. I’ll never internet date again.
11. The McDate
A couple of years ago, I met a guy in my senior class boat cruise—it’s like a semi-formal prom on a boat. He was from another school, as our senior class was sharing the boat with a few other local schools. He was nice, smart, tall, and generally attractive. We talked for a while and then exchanged numbers. After a couple of weeks had passed, we agreed to meet up.
I had to drive 45 minutes to his house because his parents “wouldn’t let him drive a car.” When I arrived, he had shaved his head and was MUCH thinner than I remembered. I’m not fat, but I prefer my men bigger than me, and this kid was really scrawny. After several awkward hours watching movies, I asked if he wanted to get something to eat. The only place he wanted to go was McDonald’s.
When we got there, he had forgotten his wallet and I had to pay. We ate in awkward silence and then I drove us back to his house. I figured he could redeem himself by being talented in bed. I made the first move and leaned in to kiss him, and within less than a minute of making out he had managed to take off every item of clothing he had on, even his socks.
Meanwhile, I am still fully dressed and really creeped out. I grabbed my phone and pretended to read a text from a friend who needed my help, and I immediately left. He never paid me back for the McDonald’s.
12. Proper Hygiene
We met online. On our first date, she invited me to her house. The house was pretty disgusting; dirty and plenty of trash around. She was remodeling her kitchen so I gave her a pass on it. The next get together was at my house. I think it was our third date, but maybe second. Anyway, we get intimate and I quickly became aware she had not bathed. She was funky, like B.O. funky.
The next day I get a frantic phone call. “I have bugs,” she said. “Bugs?” I replied, “What kind of bugs?” “Lice,” she replied. “Lice! Like upstairs or downstairs,” I asked? “Up,” she said. “I’m outside your house right now and I brought supplies.” So, she comes in with RID, trash bags, cleaning supplies, and four new pillows. She proceeded to bag everything she thought she came in contact with, throws out my pillows, and leaves me with a bottle of RID.
Fortunately, I never got lice. I still keep the RID under my sink as a reminder to be more careful in the future. I never saw or heard from her again and that was fine by me.
Homecoming formal my junior year. My first dance ever, my date picks me up 30 minutes late, and realizes he isn’t wearing a tie or appropriate shoes. We stop at the store, and he steals a tie and some shoes—because apparently he really felt like he was “sticking it to the man.” He then forgets that he never made dinner reservations, so we end up eating a $50 meal. He got steak, I got a salad.
Next, he forgets his credit card and I end up having to pay for both our meals. Oh, but it gets worse. He tells me he just took a pill, ends up freaking out at the dance, leaves me by myself, and I end up having to call a cab home. Did I mention he sat in front of me in two classes so I had to look at the back of this loser’s head for the rest of the year?
14. The Land of the Dragons
After dating a girl for about a month, she let me know that she had spent time in a mental institute two different times for trying to harm herself. She did not do it because she was depressed or anything like that. She did it so she could enter “the land of the dragons.” As if that was not bad enough, she said that she still wanted to get there some day…
15. Hot Death Metal
First, his dog peed on me. He then sat across the room when watching TV even though I was on a huge couch all by my lonely self. He took me into his room and just when I thought it was going to get hot, he showed me HOURS of all the death metal he’d composed. And then he showed me the organ he had made, and played like 25+ minutes of ORGAN for me on his HOMEMADE ORGAN.
Right before I left, he told me he wasn’t physically attracted to me—and then his dog humped me. At least someone was.
16. The Pig Roast
I went out with this one guy and it seemed to be going alright. Nothing really screamed crazy. We went bowling first then went out for dinner. During dinner, he starts talking about his sister’s stag and doe that had been the weekend before. It was a pig roast. Long story short, the guy who was supposed to cook the pig couldn’t, so this guy stepped in to help his sister out.
After the pig roast, him and some friends went back to clean up, which meant getting rid of the pig. What happened next was utterly horrifying. He then began describing to me in vivid detail how they had ripped the pig’s carcass apart, pulled its spine out, ripped its face off and wore it like a mask. I’m sitting there absolutely disgusted—I’m a huge animal lover.
I repeatedly told him to stop, but he was laughing and thought I was joking. He then pulled out his phone and wanted to show me pictures. I actually had to raise my voice for him to realize I seriously didn’t want to see pictures of him and his friends wearing a dead pigs face like a mask over dinner. We did not go out a second time.
17. An Explosive Ending
In college, at the beginning of freshman year, a friend and I took a couple of girls out to some parties. These girls seemed to be really into us, and we were getting hammered so things looked great. At one point, we’re passing around a bottle of vodka, taking swigs. After I don’t know, the sixth or seventh swig in about five minutes, it happens.
I projectile vomit on both the women. Before anyone really knows what happened, I turn around, beeline it for the door, and walk back to the other side of campus without my shirt on. I had to take it off because it was covered in puke; a lot of people taunted me on the way about it. When I got back, my roommate and I played Guitar Hero for a bit, and then I passed out. Good times.
18. Well Prepared
I’d met a girl at a bar at university and we’d exchanged numbers and arranged a meet-up. It was pretty obvious why, too. It turned out that she lived a train ride away from me, so I strolled down to the train station, needing both condoms and a pee. Walking past the university Health Services office, I decided to kill two birds with one stone and take a pee as well as grab some free condoms. Everyone wins.
So, I walk into the toilets and hey, presto, a big sign saying “FREE CONDOMS AVAILABLE HERE,” with a bowl full of silver bags below the sign. I pick one up, take a pee and get out of there. Skip forward to the meeting—the girl and I go back to her halls so I can drop my bags off. She’s the playful sort, and as I’m lying on her bed she starts going through my stuff, being all “I wonder what you’ve brought me” etc.
I don’t mind, until I realize that she might find the bag of condoms. Even though it’s pretty obvious I’m there to hook up with her, we hadn’t actually explicitly talked about it, just heavily implied it. So, I’m lying there frantically trying to come up with a smooth way to pass off the bag full of condoms without sounding like an idiot.
She finds the bag, and pulls it out with a confused look on her face and says, “What’s this?” “Uh… I thought I might need it?” is what I came up with. I guess I hadn’t looked closely at what I was grabbing. She looks confused, opens the bag, and her confusion turns into a mix of outrage, offence, and revulsion…as she pulls out a chlamydia testing kit.
19. A Really Cool Van
I got a message on a dating site from a guy about 1.5 hours away from me, saying he wished he were closer, because he felt a real connection. I was flattered; we emailed for a while, and a few weeks later, I happened to be in his area. Now, I let him know that afternoon that I could meet up at his house around 9-10 at night if he was interested.
We were too far away to have it be anything but a one-time thing. He, of course, was quite happy with this plan. I get there and I text him that I’m at the gate to his apartment complex. Now, he’d been responding immediately up to that point, suddenly he goes silent for about five minutes. Just as I’m about to leave, he comes through the gate.
He starts walking. I’m a little puzzled, because I thought I had made my intentions clear by asking if I could come over to his place, but whatever, maybe he wants to talk first—make sure I’m not crazy before he lets me in the house. And frankly, my nerve for the random hook-up was fading fast anyway. We chat as we walk, and he asks me where I’ve parked.
I point out that we walked by it a while ago, under the streetlight, so he shrugs and keeps walking. He says he needs to show me his van, because he painted it himself and it is awesome. We walk all the way around his large, scary apartment complex to the alley behind it. It’s not the exterior of the van he painted. It’s the ceiling of the back compartment, and he explains that I need to get all the way inside this van, in this alley late at night, so that I can really appreciate his artistry. It has glow in the dark paint, you see, so he has to close all of the doors so that I can see the effect.
Strangely enough, I got really tired all of a sudden—plus I had a long drive home ahead of me. Got to go, bye!
20. The Two Friends
So, I met two attractive girls at a gas station I frequent for snacks. It’s obvious they’ve just been on some sort of bender—I live less than two hours away from Las Vegas—and were very hungover. I found this funny and when they started talking to me, I humored them and chatted a bit. I gave my number to both of them and went on my way.
That night I set up a date with the one I thought was the prettiest one, and off I went to pick her up. Turns out it was the OTHER one…well, whatever. We went to get wings at this cool wing bar, and immediately, a red flag comes up. I was telling her how I enjoy playing volleyball at our local park, and she announced, “Oh yeah. Me and my AA friends do that.” Uh oh.
Instantly, I knew this was going to be a bad date. So, we eat some wings and drink some beer. She asks me if I can stop to buy her some cigarettes. She just spent her last $20 on paying some guy she knows to watch her daughter. Red flag #2. So, I buy her cigarettes, a bottle of tequila, and we proceed to the bar/dance club. While there, she proceeds to take my keys and go out to my car with friends to down the tequila.
She starts dancing with random people in the club and even at one point, proceeds to lick the faces of a table of complete strangers. This date has just hit a brick wall, so I politely tell her I’m leaving. She starts to cry and demands I go pick up her friend—the other one at the gas station. Oh boy. So, I drive around for over an hour while her drunk self tries to tell me how to pick up her friend.
After an eternity I find her and pick her up. Oh, she also has a snowboard and days’ worth of camping gear to fit in my tiny sports car. But she’s attractive, so I oblige. I drop girl #1 off, and her friend gives me her number; we hit it off. I dated her for about eight months until I (slowly) realized that she was freaking insane.
21. The Man in the White Suit
I went on a blind date with a girl who claimed she had lost 100lbs. I found it; it was in her butt. I decided not to judge and just have a good time. I am a large person myself. After about 30 minutes of dancing and drinks at her favorite club, I was getting lots of dirty looks from a club rat in a white suit. Her friends kept saying things on the order of, “I’m glad you two are together,” “you two deserve a good relationship,” and “you are so much nicer than her last boyfriend.”
I asked the last friend to point him out. Of course, it’s white suit loser over there. I realized I was being used to make this guy jealous. I looked my date straight in the eye and said, “I’ll see you sometime, I have to take a poop.” I then walked out the door and never saw her again.
22. A Complete Tool
My worst date would have to be the guy that spent the entire night listing off horrible things he’d done/said in an attempt to impress me and following up every awful story with, “I know I’m a jerk, but at least I’m honest about it”. No, that does not make you cool. It makes you a disgusting person because you’re aware of the fact that you’re a complete tool, and actually like it.
23. The Conversationalist
I had known this girl for about a year now, and she was introduced to me by my best friend. One day I just straight up asked her out. I invited her to a musical production of Charlie and the Chocolate Factory at a local theater. Everything was done by volunteers and through donations; very classy stuff. She was very excited because she had never seen a play, and loved the original. I was excited because hey, it was a date.
I show up at her place looking really nice and smelling great. She’s gorgeous as well. She hops in the car and we say the usual greetings and make small talk. Some time passes by during the car ride, and all throughout the evening, every question I asked was met with a short, closed response. I never got more than a few words out of her at any given point.
I knew in the back of my head that this was going to be a VERY long night. I’m pretty sure the only question she asked me was when she asked if I wanted anything to drink from the concession stand. The night continues to drag on and we make it through the production. As we’re walking back to the car, she literally has nothing to contribute to the conversation.
A half-hour car ride back to her place was the most quiet and awkward stretch of time I’ve ever experienced. We’re still friends, but I definitely know that it will never exceed beyond that. I honestly think that I could have had more fun going alone.
24. Old Habits
I was set up on a blind date with this guy. Handsome, polite, a gentleman with great manners and a slight Southern accent. Held the door for me and got me flowers, which I didn’t expect, but considered a very nice gesture. We’re seated at a lovely restaurant, and we order. We’re talking about school and our future careers when a very cute gay couple is seated beside us. Ugh, I can’t believe what happened next.
My date sneers and tells me he’ll get us reseated, adding vile slurs not-so-quietly under his breath. I stood up, said, “Don’t call me.”, and left the restaurant. I only wish I had dumped a drink on him or something, and have done so in my head many times since. Luckily, I knew there was a subway to get me home. The friend that had set us up had no idea he was such a jerk and nobody I know talks to him anymore.
25. A Textsunami
I was recently out of a long-term relationship that ended only because of distance, and I had started dating someone local very, very casually but I was pretty sure I wanted to keep seeing her, but I was keeping my options open. So, I sell new cars for a living, and the girl I went on the date with was a customer of mine.
Anyway, through multiple appointments and conversations she obviously had my cell phone number and the day I sold her a new car, she texted me to say what a great job I’d done and could she repay the favor by taking me out to dinner? I initially rebuked the offer, saying I didn’t think it’d be professional, and she called me out asking if I was in the business of not satisfying my customers.
My manager got wind of this conversation and started giving me nonstop chirps for not trying to seal the deal for the second time. So, I relented and agreed that she could take me out. The next day, the textsunami hit me. “Where are we going?” “Where are you taking me?” “I can’t believe you agreed to come out with me.” “What do you see in a tatted-up, foul-mouthed girl like me?” “I’m so not your type.”
All un-responded to, all within minutes of each other for HOURS on end. The only thing I eventually said via text was, “I think I made a mistake in agreeing to cross the professional-client relationship.” She still comes in, and stares daggers at me when she’s in for service.
26. The One
I was playing catch up with a woman I had dated years prior, and it seems to go well. Over the course of the next couple of days, the texts go from catching up to, “I always felt like you were the ONE.” and I start getting a strange vibe. We had only gone on a few dates and never slept together or anything—so it wasn’t like there was a huge foundation from our past.
At this point, I decide getting together is a bad idea and start making excuses why I can’t go out. Finally, after putting her off for a few weeks, she invites me over to a BBQ at her house with a bunch of friends/coworkers. I figure its casual enough not to be construed as a date and I can get a visit out of the way and be done with it. I get there and she is already smashed…ugh.
Then she introduces me to 20 strangers as, “The one I should have always been with.” Everyone just kind of stares as I’m trying to scoop my jaw off the floor. At this point, I’m making small talk with everyone else, but am randomly getting pulled aside so she can tell people I’ve never met, about how in love with she is with someone THEY have never met.
After some time, everyone starts leaving en masse and she corners me trying to slur out a few seductive lines. I’m awkwardly trying to make a break for the door. She leans in to kiss me, I do the cheek turn and say something about having to go, and then the worst happens. She grabs my hand and shoves it down the front of her jeans. Directly into a maxi pad.
She lowers her eyes and whispers, “Oops… forgot that was in there…” and walks into the bathroom. I left. No, bye. The next morning, I get a text: “Sorry about last night… was that weird?” I reply: “Yes… that was extremely weird.” She says: “Screw you.” And I haven’t heard from her since.
27. The Baptist Boy
This happened when I was first dating my wife. I’m Asian, so her very prejudiced aunt set her up on a date with a “good Southern Baptist boy” who was apparently a lot better than me. She goes, because she didn’t realize it was supposed to be a date. They went to a Halloween event at a theme park. When my wife arrived, she was shocked to find out that she was actually on a date, but couldn’t leave because he was her ride.
Turns out the good ole boy was more of a man, and by a man, I mean 15 years her senior—she was around 19 at the time. He was also an ex-con and a dealer/user. All this was better than me, of course. My wife spent the entire night not just being terrified of the haunted houses and actors in costume and makeup, but being even more afraid of the dude who wouldn’t let go of her hand, even though she kept insisting she had a boyfriend.
The night ends with the dude’s parents picking them up—he wasn’t allowed a driver’s license because of something having to do with his probation—and him trying to make out with her in the car. My wife moved out of her aunt’s house within days, moved to my city instead, and we’ve lived happily ever after.
28. Chew on This
Online dating has given me some horrors, but there’s one that really sticks out. One guy failed to mention that he didn’t have teeth. After he revealed this in person, he asked if I wanted to go get food. What?
29. The Metal Girl
Many years ago, during the dawn of online dating, I had been chatting for months with this girl I liked a lot. We decided to meet when she was house sitting. I had to take the train for eight hours and would be staying in the house with her. She had recently broken up with her boyfriend, an older metal dude—she was the metal type girl herself.
We got along very well, no problems at all. She was quite forward; we were both 18 years old. She told me she what she liked in bed—I didn’t really mind; I was young and eager. Anyway, making out started to happen, we got into bed, then she was going to go down on me. Now keep in mind this girl had been with a guy for a couple of years a little while before this.
It was the worst thing I’ve ever seen or felt. It was too hard, there was no feel, it hurt, it was horrible. Anyway, I told her to slow down, but she kind of got why I wanted her to stop, so it was a bit awkward. Intercourse didn’t happen, just finger stuff. The whole weekend went by without it; guess I was shocked by the horrible experience.
Anyway, I come home, and after a while, she tells me she never really broke up with her boyfriend.
30. Homecoming Pt. 2
I got set up on a blind date to a homecoming event/dance in college. She was pretty cute, and I was looking forward to a fun night. I went to a religious college that is owned by a church, so all school-sponsored events are kept pretty clean, including music played at events. Not five minutes after we had gotten there, she starts complaining about how inappropriate the music they were playing was, even though it was just some pop song that was popular at the time.
From there, it just went downhill. From the music they were playing at the event, to how all media today is filth, how her roommates were horrible people, etc. All within about the first hour of the date. Thankfully (sadly?) I had experience in handling crazy—and skillfully cut down the length of the date drastically. Kind of easy when she thinks everything is evil!
Next semester, I meet a new friend and find out she was one of the girl’s roommates who had moved out. The crazy girl would yell at them constantly for watching TV, because everything on it was evil and made her feel bad. On several occasions, she had turned it off while they were watching it because she didn’t approve of what was on.
She went on to meet a guy online, fly out to visit him after a week, get engaged, and marry him a month later.
31. The Partier
I’ve had an ex-girlfriend who was a certain way at parties; we would get to a party and start drinking, smoking, chatting up everyone, but then she would get really crazy and start pounding shots, beers, blunts, anything she could get her hands on—she would abuse it. We wouldn’t even be at a party more than an hour before she would get messed up and start puking.
Then she would pass out in someone’s bed, and I would be forced to sit with her all night until five hours later she just wakes up and is ready to leave.
32. Physical Love
I met a girl online and we went out. In the course of the conversation, something about a recent bust by the police comes up because the bar had a TV in it tuned to the news, and she starts to get weird. She asks if I ever use illegal substances and I said I don’t. I casually throw out, “How about you?” That’s when she told me she uses hard stuff whenever she starts to gain weight because it helps her stay skinny.
I should have just ended it there, but I didn’t because I wasn’t thinking. We go back to my place and she’s ready to go. As we’re going at it, she tells me to hit her. I ask if she means she wants to be spanked and she doesn’t. She wants to be hit. I ask if she means slapped and she says, “I guess that will do.” I try a gentle slap and she’s having none of that. She wants me to haul off and hit her, and I can’t do it.
After we’re done, she says I need to learn how to really hit her, and she’d prefer it if I’d use a fist next time. There wasn’t a next time.
33. Peaked in High School
I went on a date with a girl I was friends with in high school about two years after graduation. Now, in high school this girl was a petite, cute, very sweet girl, and I wasn’t very self-confident until after high school. So, we start texting and decide to “hang out.” We meet at a school near our homes and I see this very large woman looking under the hood of her beat up old Buick.
At this point, I’m parked wondering where she is, and I call her. I hear the woman’s phone ring. I literally shout, “What the heck!” She hears me, and then she says, “Hey, I’m right here silly!” My immediate reaction is to drive away. I’m generally a nice guy, so I’m just like hey what’s up! She gets in the car and I see her in the light and holy moly.
She looked completely different than she did in high school. I hate to say it, but I just wasn’t attracted to her. So, we go to the movies, and I end up chatting with the girl next to us. I got her number without my date knowing, and proceeded to drop my crazy date off at her house and then went out with the girl I met at the movies.
Strangely enough, I’m still in a relationship with the girl I met at the movies!
34. The Spoon Game
I went on a date one time with a guy I thought was pretty cool. I knew him from my community college. We usually just sat and talked in the honors lounge. He was awkward but in the fun kind of way. While on this date, he told me of a game he liked to play with his friends: spoons. When he explained the “rules,” my blood ran cold.
Basically, you throw spoons at black people while in a moving vehicle. If you don’t hit the person, you have to pull over and retrieve the spoon. I couldn’t believe my ears. I definitely didn’t see that one coming. I was so appalled and embarrassed. I didn’t say much the rest of the date, and I ignored his texts afterward asking me to come over for pancakes.
I ended up dropping out of school because he was one of my only friends there and I felt sick even thinking about seeing him. Ugh.
35. Orbit Theory
I went on a date with this gorgeous girl I’ve had a crush on for a while. She is thoroughly convinced that the sun revolves around the earth in a perfect circle. I paid the bill and left.
36. A Weird Feeling
It was the summer after I graduated from high school, and I agreed to go on a date with a recent college grad in his mid-20s. He picked me up, and drove me from the suburbs to a nearby train station, and we took the train to Philly. We wandered around Center City a bit, but I immediately caught on that maybe someone that was 24/25 was a bit out of my realm of maturity, especially since I think my longest relationship at that point had lasted two weeks.
He tried to lose me in a book store. But this was before smartphones, and I had no way of getting home. I couldn’t be stranded in Philadelphia, I didn’t know how to get back home, and it was night. Even though I knew what was going through his head, I followed him so he couldn’t shake me. The least he could do was be a gentleman and drive me home.
He relented, and we walked back to the subway, and he started rattling off great gems such as, “Photography is a lie…and I…am the liar.” Along with, “I always like to sit on the front of the train so I can see the tracks. One time a little kid was in the seat and I shoved him aside and told him to screw off.”
37. The Many Faces
When I was in undergrad, I had recently come out and started the whole online dating thing. So, I had talked to this nice, level-headed guy from the next college town over. He had friends that were going to be in my college town, and so he could bum a ride and we could hang out and go on a date. Oh, and conveniently, this would be Valentine’s Day.
He shows up with his friends, and I’m being polite and pleasant as I wait for them to depart and for my date and I to get to talk to one another. “What are you in town for?” I ask. They start discussing that they are going to do a Faces of Death marathon to celebrate Valentine’s Day. Because they’re edgy or something, and I’m supposed to be impressed. They discuss how they are hoping to make or be in a movie of the same style at some point.
That’s nice. I very quickly bailed on the whole situation. We’d met in a public place—near the library—and I said, “Sorry, gut says go, I’m out.” Walked to where I was out of sight and made sure they’d driven away before I called a friend to get a ride home. The guy could’ve been nice enough, I’ll never know.
38. Finding Jesus
I went on a date with a cute girl, she was also really smart. We would Skype often, and it all went fine. But once I met her, she told me I had to meet her mom and say I was gay. She was supposed to be helping me find Jesus—since her parents won’t let her date. I met her parents with them thinking I’m gay—not that I have a problem with that, by the way.
Eventually, she decided she can’t kiss or even hug until she’s engaged. There wasn’t a second date.
39. Noodle Date
My worst date was a guy I met online—I’m a gay guy. I mentioned I had never had Vietnamese noodles before, so he said I should try it out, and we went to a pho place. We sit down, make some small talk, and he walks me through the menu. The first question out of his mouth was asking if I was Jewish. Understandable, because I mentioned that I can’t eat shellfish or pork, but I didn’t mention it was due to allergies and preference, so he assumed I was keeping kosher.
The next thing he decides to bring up is that he is not gay, but he wanted to see what a date with another guy would be like. Finally, he goes for the hat trick, and says that he doesn’t think gay people should want to be able to get married because it is just the government interfering with our lives. Needless to say, at the end of the date I told him he was self-absorbed and walked back to the bus stop.
40. The Hesitator
I went to dinner recently, and my date came back to smoke at mine afterward. I had full intention of kissing her, but when we got into my room, I didn’t close the door behind us and felt weird about getting up once we were sitting because I didn’t want it to come off as “LET’S HOOK UP NOW.” Also, my roommate was in the living room and could her us joking around and would let out the odd chuckle making me super self-conscious.
At one point I decided to make the jump but was so in my head that I only half jumped. What I mean is, when we hit a lull, I put my arm around her and instead of kissing her, just leaned us both back so we were laying down—THAT’S IT. I just laid there awkwardly for a few minutes until she said she had to go. Never saw her again.
41. Footing the Bill
I’ve mentioned this one other time. I once went on a date with a guy, and while we were driving to dinner, we got a speeding ticket. He asked me to pay for the ticket, because I was distracting him, and then took me to dinner where he made me foot the bill. After that, he took me to a night club, where he told me about other girls he brought there.
I then made him take me home and told him to forget my number.
42. Some People Have a Type: Insane
I once had a girl throw up in her purse because she was allergic to something in my dish—that she had insisted on nibbling. I then saw an ex of mine in the same restaurant, who was, at the time, the reigning queen of crazy exes. She comes over and tries to kiss me out of the blue. Somehow, it gets even crazier. My date then throws purse full of puke at ex.
I narrowly dodge it all. My ex throws breadsticks and salad at the date. They begin to physically fight. I ran to the kitchen, found my server, gave her a $50, told her to keep the change, and got out of there. And that is the story of the Puke Purse and the Olive Garden. Also known as: Why I won’t go to any Olive Garden in Indiana ever again.
43. The Cheap Hotel
I met this guy online. His wife had supposedly died of cancer and he had two kids. He lived several states away. He seemed pretty perfect. After a few months, he drives out so we can meet in person. We meet up in the parking lot of a cheap hotel—kind of late at night because I had to work, and he had to get his kids settled after arriving in town.
I follow him to his room and right before we get there, I realize that I really know nothing about this guy and he could have lied to me about having his kids in the room. I say as much, and he laughs kind of creepy. Then he opened the door and there were two small children in there. Three months later we got married. Four years later, we have two more kids and he continues to seem pretty perfect.
44. The Secret Admirer
I just finished dating the craziest of the crazy. We’d had quite a few incidents together and it ended with me calling her dad; who then called her and threatened to report her car stolen if she didn’t come home and quit stalking me around town…and that’s not even the half of it. So, a month or so later I get a flower and a note on my car from a “secret admirer” saying she’s been watching me for some time but is too shy to meet me.
I know it’s my ex, it has to be, so I pass it off. She leaves another note with an email address and I send her an email telling her I know who she is and to leave me alone. She insists she isn’t my ex and we go back and forth a few times about it. I caught her defending my ex a few times, which was the clearest giveaway.
A few weeks go by, with me continuing to try and ignore this situation and finally she says she wants to call me to prove she isn’t my ex—even though she’s already claimed to know her at this point. I say what the heck, and give her my cell number, since my ex already had it. Sure enough, later that night I get a call from a number I don’t recognize. I answer, even though I’m pretty sick of dealing with her crap at this point.
Lo and behold there’s a girl with a voice I don’t recognize claiming to be this admirer on the other end. At first, I had a hard time believing it, but I know my ex’s voice and this definitely wasn’t her. The girl took ownership for all the things that happened and even answered a few suspicious questions about her alleged events. She finally says she has to go because she’s at work and hangs up.
I’m shocked. I’d never had anyone do anything like that for me before and I’m a romantic deep down so at this point, I’m pretty entangled. Finally, she says she wants to meet and I—eagerly, with my heart on my sleeve, agree. We go to a bar I usually frequent and I grab a stool at the bar and order a drink. Finally, the bartender walks over and sets down a beer in front of me saying a young lady bought it for me.
I ask him to point her out and follow his index finger across the bar to a table. I should’ve known. Sure enough, there at the table sat my ex. I told him to dump the drink down the sink and stormed over to her, as angry with her as I was at myself for being so stupid. The only thing that didn’t make sense was the phone call, so I demanded she explain.
She finally gave in and told me she put her roommate up to it, which was pretty crushing. I couldn’t believe another human being would let her brief her on everything that’d been going on and pretend to be this girl just to screw with me. After that, I left and told her if she ever talked to me again, I’d get a restraining order.
45. The Spicy Date
My first date ever. I went for a blind date downtown. At the time I lived in the suburbs, so it was an hour by public transit. We met up at a Thai restaurant and ended up ordering the same dish. The food was spicy and all the heat came from one pepper per dish. We dared each other to eat our pepper. He spat it out. I didn’t.
I took three trips to the washroom within the next hour and drank a lot of milk, provided by the restaurant as a courtesy. The conversation was terse. I felt awkward. Is this how a date is supposed to go? We left and, since neither of us were familiar with the area, we went to some nearby department store to window shop.
We ended up in separate parts of the store, mostly because we didn’t have very much in common. I’m thinking about how much longer this date is going to last when I feel it. A rumbling in my bowels. I knew at that point that I had to go to the bathroom immediately. It wasn’t something that was going to be negotiated.
I make a mad dash to the nearest store employee, who informs me there isn’t a washroom in the store. The guy is nowhere in sight so I run off to a place next door where they reluctantly let me use their basement toilet. Too late. I poop my pants on the way down. I spend the next hour cleaning up in the washroom with an ungodly amount of toilet paper.
There’s no cell service, so I can’t call the guy with some quick excuse. By the time I get out, he’s long gone, not that I really wanted to see him at that point. I was supposed to see a friend around that time but he assumed I ditched. That’s not too bad. The worst part was that I had to take the subway back, an hour commute, with a mess hidden in my pants and, oh god, I’m sure people knew.
46. Alarm Bells
I met a guy online and suggested that we go for a drink. He said he doesn’t drink, which I didn’t think anything of at the time, so we met for dinner. Super attractive guy, got along well, but throughout the conversation it came up that he didn’t have a car. I asked why, and he told me, there had been an accident but it’s hard to talk about.
Silly me, thinks he was probably injured in the accident and so I just let it go. Then he drops on me that he has to be home by 10, because he lives with his mom and has a curfew. Ok, now I’m weirded out but I assume this curfew is his mother’s doing. So, I ask if she’s just really strict or if he did something to deserve a curfew. He said he deserves it.
Now the alarm bells are going but I still stupidly offer him a ride home so he doesn’t have to take the bus. Keep in mind, my last boyfriend lived with his parents so it wasn’t a totally weird situation to me…though it was getting there. We get back to his place and sit in his driveway talking for a bit and it finally comes out that this “accident” was him getting drunk and driving the wrong way down a one-way street. But it doesn’t end there.
He had also run over a pedestrian, killing her. He was brought up on charges of manslaughter and was currently out on bail while awaiting trial. Now, this is bad enough, but what really sealed the deal, and this is 100% true, at this very moment a woman walks up to the car, bends over to look in my window, and screams, “I KNEW IT!”
She then starts shrieking at my date in French. My French isn’t great so I didn’t catch most of it. She then turns around, gets in her car, and peels off. My date apologized and said, I swear, she’s not like my girlfriend or anything! I just quietly said, “I think I should go.” It honestly didn’t even feel real. And there you have it.
47. Buffalo Wild Wings
I was out to lunch with a co-worker and his girlfriend, and she needed to know why I was single. She likes to play match-maker a lot and she just HAD to set me up. Oh, how ominous. So, I got this girl’s number and on day 1 we have a pleasant exchange of information via cell phone (text only). Day 2, she started texting me a lot more.
This girl decides that we need to take turns asking each other anything-goes questions, responding honestly, and then returning a different question. Ok, this is bearable and not that weird. So, this goes on literally like all day. From like 3 pm until midnight or 1 am. Anytime I start taking too long in between text messages, she texts me random song lyrics from wildly different genres.
Day 3, I am busy with work most of the day and I don’t text her until like 9 pm at night and she’s being a little “moody” expressing her concern about why we weren’t texting 200 times again today. Day 4 is date night. I agree to meet her at Buffalo Wild Wings. She chooses the time, I agree, we state that we will meet and whoever gets there first will get a table. 7:45 pm is our rendezvous time.
I’m early for everything, but I held myself off and waited until about 7:50 to walk in, hopeful she had got us a spot. Nope, not there yet. No big deal. I get a table, have a nice chat with the cute waitress. 10, 15 minutes goes by and I get a text that she is running late. Yeah, no kidding. I tell her where I am sitting. I order a beer to pass the time. 25 minutes have gone. Still nothing.
I order some potato wedges and another beer and text her again. She’s “on the way.” I decide internally that when my beer is done, I pay and leave. Unfortunately, the potato wedges and the football on TV slow me down and 45 minutes have gone by and I am just about to find the waitress and pay up…I turn my head and there is my date.
We greet and say hey and she tells me a little bit more about herself and over the next 10-20 minutes she takes me on a magical voyage of vapid, unrestrained blathering. She is one of those people who constantly makes comments about how she is “just so quirky” and how witty and clever she is. And she does these weird, side-ways smiles and strange looks after every sentence because hey, she’s just so quirky right?
Eventually, dinner happens, and she takes like 35 minutes to eat like six freaking boneless wings. After she finishes, I make every effort possible to alert our waitress I am ready. This girl was great, she keyed in on me right away and knew I was patiently waiting (and looked like I was being stood up) and was very diligent about coming by and exchanging a quick chat with me while I nursed my beers.
I grabbed her, got the bill, tipped well, and left. I just got it all on one bill and paid for this blind date. I told her, “You can pay when you take me out next week!” With the fakest smile anyone has ever mustered. After my blind date finally left and went back to her car, I handed the ticket to my waitress. She took out the customer-copy receipt and wrote her number on the back and handed it to me.
I gave an admittedly confused look. “I was with you for the whole thing, and that was brutal. You’re a saint. Let me take you out and redeem woman-kind. Any man who would wait for someone like that for 45 minutes is at least worth that.” Been with her 1.5 years strong!
48. Enter the Matrix
So, I was talking to this girl online and she was the one that initiated the first contact by commenting on my pictures and saying that she thinks I look good. We started chatting after that, talking on the phone and everything seemed to be just fine, and then she invited me to come and visit her, so I accepted the invitation. This was the start of one of the most awkward experiences of my life.
I had to take the bus an hour outside of my town, and I had to ask the bus driver to stop at a location where the bus ordinarily doesn’t stop because this girl lived somewhere remote. I got out of the bus and I met her, and she was dressed like Trinity from The Matrix. We started walking into the nearby forest, and right away I start to feel uneasy about this.
The road wasn’t lit and there were no houses; nothing, just trees and darkness. We walked in silence since she wasn’t able to hold up her part of the conversation—she replied with one word or just remained silent. I should have turned around at this point, but I was trying to be open-minded when it came to dating.
After a while, a little boy appears on a bike and he rides it in circles around us; falling over every now and then, biking off the road, occasionally hits a tree. The girl doesn’t mind this at all. At some point, I have to ask: “Who is this? Do you know him?”—“Don’t mind him, he is mentally challenged.”—“What?”—“It’s my brother, there’s something wrong with him.”
The situation starts to become surreal. I’m walking through a moonlit road in the forest with Trinity and her mentally challenged brother. Until I finally see it…the house. This scene is taken straight out of a horror movie. It’s just one lonely house in the middle of the forest. When I see the house, my initial thought is: “This is where I’m going to die.”
But I get into the house, and I meet her father at the door, he doesn’t understand what I’m doing when I try to shake his hand. I don’t think Trinity has told him that she was going to have company over, and I guess they never have guests here. We walked over to her bedroom, and this is where it gets really weird because her walls are black.
On the wall, she has painted this Satanist symbol. The room is lit by candles and her bed has skulls on the bedpost. There is nothing else in this room, and then she proceeds to sit on the floor and starts to ask me repeatedly: “What should we do?” I’m paralyzed by fear at this point, but I have to ask: “So you are a Satanist?”—“Yes, I worship the Devil.”—“Do you melt in sunlight?” I actually asked this, and she laughed.
I then asked: “Is that why you live like this? Because the villagers have driven your family away?” She laughs again. I the other hand, am completely serious. Then her mother storms in and yells: “Stop screwing around, it’s time for dinner.” Then she asks me, “Do you eat goat?” I’m stunned. After what seems like an eternity, I replied that I’m fine.
But I’m here, with a Satanist in the middle of the forest and the family eats goat. That goat had to have been sacrificed in some sort of ritual to please the Devil. I thought: “Oh, alright, I have to survive this, I have to be polite, these people have to lead me back to the bus stop.” So, I put on my brave face, suffer through the evening, I even make out with Trinity just to ensure that I was going to be able to leave.
I get a ride to the bus and on the way, she forces me to hold her hand in the car. And the moment I leave the car the texts start piling up, with her telling me that “It feels like you love me.” When I was secured on the bus I replied: “You will never see me again.” I had to cut a lot of things out, for example, that she spent the entire evening talking about her ex-boyfriend; an alcoholic that never got dressed unless somebody told him to get dressed, and that got her number by stalking her for a month and so forth. It’s just the most bizarre thing I have ever been through.
49. The First Cut Is The Deepest
It was the first date I’d ever been on. I wasn’t the most talkative guy in school, but I rather fancied her so I worked up the courage to ask one day—and to my surprise, she said yes. We were both 15/16 years old at the time. I get a ride to her place from my mom, we pick her up and head over to this restaurant in one of the classier parts of town.
We get dropped off, head in, make light conversation and I find out she’s never been there before. I’d only been there once myself for my birthday, a year or two ago. She asks me to order for her and I do so; two steaks with the trimmings. Anyway, things continue rather pleasantly and our food arrives. We dig in and continue to talk but I notice about 15 minutes in that she’s gone a little cold on me and she hasn’t yet touched her steak. She’s picking off the veg and potatoes around the side, but the steak is untouched.
My natural reaction is that I didn’t ask if she had any dietary restrictions; so, I apologize immediately and ask if she doesn’t eat meat. Her response is so disturbing it’s unforgettable. She says she does eat meat, but: “I’m waiting for you to cut up my food for me!” Apparently, at the age of 15 years old, she’d never once had to eat a slab of meat that wasn’t first cut up for her by either her parents or whomever else she was with at the time.
I was surprised, but I taught her how to cut up her own food—seriously, girl didn’t seem like she’d ever held a knife before—and afterward, we dropped her off at her place in silence. So…thus ended my first date, and last date with her.
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?