Sure, dating can lead to everlasting love, but it can also lead to drama, stress, and craziness…and by that, we mean real craziness. Take it from these people: They rolled the dice and suffered through some stinkers. Their stories are part hilarious, part horror, and all cautionary tale. From awkward moments to disturbing dates, these people prove that modern love is a wild ride.
1. Mary’s Not Here, Man
I was supposed to meet this woman, Mary. I got to the designated spot 20 minutes early. No one for a while. About 15 minutes after I was supposed to meet her, a woman walks by. “Are you Mary?” I asked her. “Are you [arichi]?” she asked me. “Yes, I am.” She replied, “I’m not Mary.”
2. The Last Dance
The guy played Dance Dance Revolution for a good 45 minutes while I just stood there. I left and played a couple arcade games by myself, then came back and he was still playing. Then it somehow got worse. On the car ride home, he asked how many children I wanted and started suggesting names for “our kids.” Then he tried to make out with me. Nope nope nope.
3. Paging Dr. Freud
I went out with a guy who talked about his mother literally the entire time. I knew her favorite foods, movies, where she went to college, how she makes her spaghetti sauce…you name it, I heard it. At one point I suggested he date his mom since no other person could compare to her. He looks at me almost like he’s contemplating it.
I look at him like he’s psychotic, and he yells at me and says that anyone who is half the woman his mother is should get down on their knees and thank God for their blessing. Fast forward two years and he married his dad’s high school sweetheart. True story.
4. Shaken, or Crushed?
Drove a total of six hours to meet a guy I was talking to online who seemed nice. We saw a movie together which was largely uneventful, and we got back to his car and he starts telling me to crush his junk.
5. Worst First Kiss
I went on a date with a handsome, smart, funny guy who was getting his PhD in mechanical engineering. We had a fantastic time though he did get a little awkward with his humor at times. Normally I don’t kiss on the first date, but I had such a nice time, so when he walked me back to my car and went in for the kiss, I reciprocated. Holy. Ouch. Terrible.
I couldn’t get away. I made up some lame excuse, “I gotta go let the dog out,” and left. The next morning, I woke up with a bruised lip. Five days later, I went to the ER, sicker than I’d ever been. It Turned out I had mono AND strep throat. I wrote him a text apologizing saying that he might want to go to the doctor…his response? “LOL. I had that.” He gave it to me.
6. Really Nosy
I went on a date after talking to this guy for a few weeks and I told him I was thinking of getting my nose pierced but was afraid it would hurt. We are walking through a park in broad daylight and this dude takes a safety pin out of his pocket and jams it through his nostril. Blood pours down his face. He laughs and says, “See? No big deal.”
7. The Cherry On Top
I was set up by a friend when I was 16. He took me to the movies (at the mall) and awkwardly tried to make out. Then we sat in the food court and he asked my honest opinion of him. I mumbled something typical like, “You seem nice.” Without invitation, he then delved into what he thought of me, which was attractive but could be really hot if I lost 5-10lbs. Then he left me for a bit, which was weird, and returned with a lovely gift…a creepy puppet.
8. Chance McMeeting
This girl I matched with just messaged to mess with me. I was like, “Hey what’s up” and she was like “Don’t talk to me unless you plan on doing me.” I forgot what my reply was but she obviously never messaged back. Then a week later I’m getting McDonald’s and this girl was the one who handed me my food. She recognizes me instantly and just had this total look of fear in her eyes. I walked out of there so quick. That poor girl thought I purposely sought her out to confront her or something.
9. Foot Problems
I went to his place and we hooked up, but after he goes “So you wanna know what I’m really into?” And I was like sure and then he grabs my foot. I have a really irrational fear of people touching my feet so I ran the heck out of there. Anyway I get to the living room on the way out and it turns out to be his parent’s house and I look at his mother and see she was my old therapist.
10. Up In Smoke
Picked up my blind date from a sober living house. Went to the park and ate some sandwiches she made. She was so nervous she smoked an entire pack of cigs (or what was left anyway). Before taking her back home because she couldn’t relax, she had me stop at the store. She came out with an entire carton. Then I took her home.
11. Punning Photos
My dad had been on Match.com for about three months with some success as he’s a tall Australian man who’s decent looking so he had some interest. One weekend he got sent his first “sexy pic” which he thought had strange, but brushed it off. Later that week he got six more pictures from the same woman. Before he blocked her, he decided that he would open them just for kicks.
Five of the pictures are just straight up coochie shots, which he said were incredibly unappealing and had terrible lighting. The sixth picture however was something different. The woman was standing in her bra in front of a mirror, no bottoms, winking, with a bunch of herbs shoved in her bra. Basil, parsley, thyme, all that good stuff. The caption on the picture was “spice rack.” She was swiftly blocked after my dad stopped laughing long enough to find the block button.
12. Blame It on the Mai Tai
I went on a Tinder date a couple months ago on a Sunday afternoon. I met up with the guy around 3, he had a really good energy and was funny and complimentary. The place we wanted to go had a long line, so we went to another restaurant on the water for a drink and appetizers. He started slamming down Mai Tais. I had one, he had three, and they were STRONG.
He got drunker and drunker and started telling me he loved me, joking at first but getting increasingly serious. As we left, he asked me to marry him, I kind of laughed it off, and was like “maybe we take it slow, we just met each other.” He got so mad he stormed off and left me on a street corner. Then as soon as he got home around 5 PM, he started texting me “come over.” And “I miss you.” He was 43.
13. Please Do Not Touch
I met a guy, chatted, and he seemed relatively normal. We go for our first date in a pub, a well-lit pub. We’re having a couple drinks, talking and whatnot, I see his hands under the table, moving around. It cannot be. OH. BUT IT IS. He was touching himself. Apparently, I was turning him on too much and he couldn’t help himself. The date ended pretty quickly after that.
The follow-up is when I got home, he’d sent me an epically long email about how I was fat and ugly and a tease and even worse things. Oh, and ended it with the phrase, “Don’t bother responding, because I will not read it.” Done and done!
14. Following up in Person
We were supposed to meet at 9 PM. He fell asleep and called me at 9:30 when I was already at the carnival. I told him not to bother coming as I didn’t want to see him. He asked for another chance and I agreed. Unfortunately, my dad got really ill and had to spend the next six weeks in the hospital with me visiting him daily. I had no time for dates and he got extremely mad.
He made a fake Instagram account which he used to follow me and everybody that I followed. He then saw me in a friend’s Instagram story and showed up to the restaurant we were at. He called me a liar and we had to threaten to call the authorities because he would not leave.
15. Fossil-Like Opinions
I once went on a date with a girl and this is how the conversation went: Her: “So, what’s your favorite book?” Me: “Tough, but when I was little I LOVED Jurassic Park.” Her: “Yuck, Jurassic Park.” Me: “The book or the movie? EVERYBODY loves Jurassic PARK!” Her: “I don’t believe in dinosaurs.” Me: “Fossils?!??!??!” I was already at the end of my rope, but her next response just blew my mind.
Her: “I don’t want to get into it, but I think fossils are BS.” I ended the conversation there and held onto the night. Until later on when she told me, “I don’t believe in outer space,” and my head freaking exploded.
16. Mission Failed
I wasn’t feeling great, but decided to meet anyway. We met at a Belgian beer bar. She was gorgeous, fun, and totally into me. I felt a gas pain, so I leaned forward slightly to quietly relieve the pressure. I completely and explosively pooped myself. The odor was immediate. I excused myself to the bathroom, but the damage was too great.
I walked out of the bathroom, muddy-panted, out of the bar, and boarded the train for home. The date was nothing compared to the horror of the following three weeks, recovering from E-coli.
17. Wetting the Bed
I met this girl on Tinder and went for a lunch date. We had a pretty good connection so we decided to have dinner as well. After having a few drinks, one thing led to another and we ended up back at my place. We hooked up and went to sleep. Middle the night I wake up. She’s intensely staring at me while she’s crouched behind the bed. I asked her if everything is alright, she said yes and got back into bed…I thought “little creepy, but probably nothing to worry about.” I was so wrong.
She lays down to cuddle with me and she’s wet. At the time, I was like “dang I must just be a stallion.” Fast forward to the morning, she’s gone and there’s a wet puddle beside the bed. She peed on my floor. I still don’t understand it. I had a bathroom, but maybe she just got lost and couldn’t hold it? I did not hear from her again.
18. Just Like Mom
I talked to this guy for two weeks before we went out and no red flags so we ended up going out to dinner. I said I hadn’t been out in a while because I was trying to save money for a washer and dryer. He told me instead of saving for that I should save for a boob job. I didn’t even know how to reply so he followed up with, “No it’s not a bad thing, my sister and Mom both small chested and got boob jobs and they look amazing.”
This is all before the waitress even brought our drinks. I just got up and left.
I was set up on a blind date with my roommate’s girlfriend’s roommate. It was actually a double-date, and we walked from their place to a Mexican restaurant nearby. On the way there, we saw my date’s ex drive by (they’d broken up fairly recently after a long relationship). She, apparently, was assured that we were all just going to dinner as friends and that this most definitely was not a date, so she vented about her ex several times over the course of the meal.
It wasn’t until I paid for her meal that she realized that it was, in fact, a date. I, of course, thought that she was a crazy girl, and I had just been burned by another crazy girl, so I was wasn’t going to make that mistake again. That was eight-and-a-half years ago. Right now, our three-year-old daughter is playing with her toy trains in our living room.
20. All She Does is Wine, Wine, Wine
I met a girl online and we talked maybe three times over the course of a couple of weeks. Then one night out of the blue she texts and asks if she should come over with a bottle of wine…I say sure, since she seemed pretty cool. She turns up half an hour later with an open bottle of wine she has half emptied already. She finishes that off within 10 minutes and I open another bottle, which is gone in another half an hour.
She passes out in my bed, waking up occasionally, trying to kiss me. She then pees in my bed and doesn’t wake up for three hours. I played PlayStation.
21. No Biting
I met a guy, decent conversation, smart, funny, mutual nerdy hobbies. We decide to meet up at the local gamer bar and play some games while having our first date. Get in, sit down, dude has no teeth. He says a hack dentist told him they all had to be removed, couldn’t get dentures due to budget, needed to wait for bone shards go fall out of his gums, etc.
He proceeded to spit all over our food while talking, which granted, I knew he couldn’t help, but if he can hide something this big from someone, what else could he be hiding? Plus, I couldn’t stomach the thought of making out with someone with no teeth.
22. All Mucked Up
Well I’ve only gone on one Tinder date, we talked for a bit and I agreed to pick her up at Starbucks. She looked nothing like her pictures, but I thought I should be nice and at least hang out with her for a bit. We went to her place and the entire house reeked like cat pee. Like saturated. Then as she proceeded to show me her massive collection of insane adult toys, she screamed at her chihuahua and smacked it right on the nose and without missing a beat just asks if I want to make out on the couch. I awkwardly sat down and pretended to look at my phone and made up that my grandma was dying so I could leave.
23. Stealing Waves
I matched with this cute girl a few years back and we went out for drinks. It was going well and we decided to head out to the beach with a six pack to star gaze and make out. Somehow, we ended up on a stolen sailboat at 2 AM with her ex, an old drunken boat repairman who made copies of the keys to get into the boat, and her dog.
After arguing with her ex for thirty minutes she blacks out and falls asleep. Her dog is scared out of its mind and is pooping everywhere. Her ex starts tripping on acid and yells at me that I have to take care of her and never hurt her, then runs to the bow of the boat to finish his trip. The old drunken boat thief is just chilling and chugging vodka like it was water. I said screw this, cleaned up after the dog, and brought the poor pup inside the cabin with me, then passed out.
The next morning, I woke up to the girl and her ex screaming at each other about some car crash and whose fault it was. The old boat thief was gone and I had no clue where I parked. I left without them noticing, got some coffee and breakfast, and wandered around the harbor until I found my car. Never talked with her again, but I didn’t delete Tinder.
24. No Match
When I was very young, probably around 12 or 13, an older friend of mine asked me if I wanted to go to a shop with him. I said I didn’t have any problems with it and happily went along. On the way there he said he was meeting up with a girl and asked if I’d mind talking to her sister. Her sister was severely handicapped and in a wheelchair.
Of course, I didn’t find this out until I met her. The girl then decided she didn’t like me and proceeded to insult me.
Not my story, but a friend of mine used to have a weekly get-together at his apartment on Fridays. One Friday there was this round/plump goth girl who my friend had met online. He had apparently been exchanging messages with her and had invited her to the party to get to know her better. However, whenever my friend turned his back, this girl would rub up against whatever guy was closest to her (most of the guys didn’t enjoy this, nor were they sure what to do).
Later in the night (after I had left) she ended up making out with two of the party-goers. However, my friend would later say that they’d hooked up before the party began, so the joke was on them.
26. Doggone Reality
I matched with a cute girl who seemed to have all the same nerdy hobbies as I did. We set up a date at a bar close to my place. We had GREAT conversation over text, so I assumed it would go the same in person. Boy was I wrong. She barely said a single word even with my prompting her with conversation starting questions and finally she goes, “you’re a dog person, aren’t you?” I blinked a little confused and just said, “yeah?” And she goes, “yeah I could tell, you’re way too excitable and I’m a cat person.” I mean, fine? We can like different animals, right?
But THEN she goes on and on about how she’s just like a cat and how me being a dog just wouldn’t work. From then on out anything we talked about would lead back to her being a cat and me being a dog. It got WEIRD. I finished my beer and told her I had to be up early and left. I still don’t know how the great text conversations led to THAT but hey, what do I know? I’m just a dumb dog.
27. Kissing in 3D
This super smooth guy said to me, within the first hour, “I’m sorry, I just really want to make out with you right now.” Later, after I obviously was all, “Um, I’d like to get to know you better first,” he took me to a 3D Imax movie about bugs. (Back when 3D was reserved for science!) The movie was cool, but then he leaned over to me with those glasses on…he was trying to kiss me with those glasses on…
28. Just a Couple Drinks
Met a girl from the internet. Went to a local bar where she was having happy hour with her coworkers. When I showed up, I realized that she must have started competition eating between the time the pictures were taken and the time I met her. A little awkward, but I didn’t really care too much, and her one coworker was hot (think Uma Thurman from Pulp Fiction) so I was down to chill.
We sit down and my “date” starts slamming drinks. Within 45 minutes she has become the loudest and most belligerently drunk person in the bar. Everyone is looking at us. After a bit, I politely excuse myself and say that I’m going to head home. She starts yelling at me, calling me a wimp, etc…I’m like, “what is happening,” and just walk out the front door.
She follows me, yelling…it was quite awesome. Then she sends me texts later telling me she went home with one of the guys at the bar and that I don’t know what I’m missing. It was awesome! I laid off the OkCupid for a while after that.
29. Gone with the Wind
My buddy hooked up with this girl he’d been talking to for a while. They met early in the afternoon on a Sunday for a walk in the park. Sunny spring day, things are going well. He’d been out drinking the day before and his stomach starts acting up and he realizes he needs to pass gas. This one will not only smell but will probably be loud as well. He spots a tin can a few yards down the pathway, and gets this brilliant idea that he’s going to kick it simultaneously with his gas to cover up the sound.
So, he runs up to the can, to get a few yards between them, takes aim and kicks, and misses the can. The effort only increases the volume. On top of it all he realized he probably pooped his pants a little bit as well. Without hesitation he just keeps on running and doesn’t look back. From her perspective, she’s having a nice walk with this guy who suddenly starts running, kicks in the air, rips a huge one, and keeps running Forrest Gump style.
30. First Date in a Dream State
This happened before Tinder during the transition between Myspace and Facebook eras. I meet a girl on Myspace and agree to meet at a local bar where I’m friends with the bartender and lots of people. She is from the other side of town. At the time the “Sparks” drink is all the rage and is a combo of a super strong energy drink and malt liquor similar to fourloko.
We really hit it off and are crushing tons of these drinks which are packed with caffeine. The bar closes and we go back to my place, sleep together, and pass out somehow. Eventually I wake up to her naked walking out of the bedroom and naturally assume she went to the bathroom, but she never comes back. Finally, 20 minutes or so later, I get up and search the house. I get to my garage and my car is missing.
Then I get a call from her mom. She had driven my car, which was a manual, half way home and got it stuck on a tall sidewalk and smoked the clutch. The authorities came and she was naked and not coherent. They booked her for reckless driving but all agreed that she was sleep-walking probably due to the mass amounts of caffeine. She was super apologetic and her grandfather paid for the damage to the car. I gave her another shot and we’ve been married for 10 years, have three sons, and a hilarious first date story.
31. Short Getaway
My friend matched with a guy and turned up to their date. He told her he was 6 ft. and was WAY shorter than that. Then he kept telling her how he would murder someone and get away with it during the entire date. There was no second one.
32. Nuts About You(SSR)
This girl I went out with would not shut up about her love of communism and her hatred of peanuts. For three hours every single subject I brought up somehow turned into either how we need a new Soviet Union or how peanuts are the worst thing ever. She wasn’t allergic or anything. She just for some reason really, really hated peanuts.
She ordered a very expensive non-alcoholic cocktail and then didn’t split the bill, all I had was a single Heineken. She was also a bit of a catfish as she was hardly as attractive as the pictures, but I’d roll with it, except for the peanut thing. Why peanuts? Sometimes I remember and wonder. Peanuts?
33. Videogames Are Expensive, Babe
Once went on a date with a guy from work (bad idea) who took me to Dave and Buster’s. During the meal, he said all of the following:
- I have a short attention span and can’t date a single girl for over three months.
- I want to become a professional video game player.
- I want to train to be a professional eater.
- I don’t want to work a day in my life. I just want to play paintball.
He was 23 years old, and I was 20. Even I knew this was childish nonsense. Later on, at the movie, he asked if I would pay for our tickets because he ran out of money on our $25 dinner at the arcade.
34. Hollywood Escape
On OkCupid, summer 2006, I met a girl in West Hollywood and we went to dinner. She turned out to be way bigger than her pictures, insanely rich, was Ozzie Osborn’s cardiologist’s daughter or something like that, and had a bad substance habit. The whole date she was doing stuff in the bathroom and barely ate her food. Then afterward, we went back to her place where she visibly spiked my drink with a mickey.
Then she asked me to tie her up, and then refused to allow me to drive my car out of her garage, leaving me to wait in my car all night until the morning when I followed someone out. She called three days later to say that I caused her miscarriage. I did not know she was pregnant.
35. Petty Theft
When I worked as a bartender for a while, this one girl who was a regular came in and told me about an awful Tinder date she had. Not sure of the specifics, but it wasn’t bad enough for her to not bring him home afterward. He leaves the next morning, she brushes it off as a one-night stand, and a few days later, her debit card gets declined.
Odd, since she is a bartender herself at a fairly busy place in our city and is good about saving and usually flush with cash. She goes to check her debit card and it turns out there were a bunch of charges at Best Buy, Grubhub, a bunch of other stuff. Curious, she checks her credit card too. There she found a bunch of charges for streaming services—Netflix, Hulu, everything.
She goes to confront the guy and finds out he deleted his profile. But she remembers a friend they had in common on Facebook. She reaches out to the mutual friend to try and track him down and it turns out he did the exact same thing to that mutual friend. I’m not sure of the outcome, but she was out for blood after a mediocre hookup turned into a serious case of identity theft.
36. Laying My Eyes on You
I messaged a girl who wanted to meet up, so I go out to the coffee shop and she’s not there. I ask her what’s up and she totally admits to being a dude catfishing me just so he could check me out in public, and goes on a rant about what a shame it is that I’m a lesbian because he’d totally sleep with me. I feel like the creepiest part for me was that he never once tried to get naked pics or anything, which I’d at least understand the effort for, he just wanted to stare at me in public.
37. Up in Palms
I made the mistake of taking this girl out around my friends. She started reading palms and telling everyone they were going to have miscarriages and abortions. Everyone.
38. Hands to Yourself
This woman seemed really cool. We were both 25, she’d just finished her masters, and was job hunting. She was fit, witty, and had piercings. I was a fan. We meet. Well, fit was apparently five years prior, but there was a 70-85 lb. difference from photo to reality and she was “trying to get back to her normal weight” and so thought it appropriate to use the older photos.
I’m a pretty fit guy and have always been fairly health conscious so this doesn’t appeal to me, but we can be friends. She’s witty though, so we talk. Where’s the wit? I toss her a couple of verbal jousts. Nothing. It turns out her roommate had been helping her reply to messages. That’s cool, I can be friends with nice people who aren’t witty.
Okay, well her nose ring is actually a weirdly shiny wart that she tries to pass off as a nose ring because she’s embarrassed by it. All of this isn’t the worst part though. We were out for dinner and went to a decent gourmet pizza joint with low lights, thin crusts, and wine. Without asking, she reaches over and starts picking toppings of my pizza. Pardon me, but keep your hands off my prosciutto! It was unforgivable.
39. Got a Spare
I met a woman for a date and there wasn’t lot of chemistry, but she worked two interesting jobs, and there were no real warning signs. For a second date she invites me to this picnic campout thing where she didn’t know the people very well. We talk about how most of her friends are guys and most of mine are girls. She says she is bringing her “crew” along. The crew turns out to be another guy and 2 dogs.
I engage the guy, he is super friendly and nice, spends his time fetching things for her, playing with children. We know some of the same people. After about 5 hours that I’m sitting alone with her, and ask, “How long have you known Tim?” She says, “Oh, I meet him through OkCupid 3 months ago. He’s going through a divorce and he’s not sure if he is going to have his kids or not, and I don’t want to date anyone with children.”
40. Aborting This Date
I went on a blind date two years ago with a guy one of my good friends set me up with. He just started university at USC and was majoring in political science. I thought he sounded pretty smart from what my friend told me and agreed. We met at Laguna Beach and had dinner at The Greeter’s Restaurant, which is this cute little place that doesn’t have the best decor, but has good food with large portions.
It was fine at first because he was cute and we had some things in common like music and traveling. It wasn’t until he started mentioning that he did not support gay marriage and abortions and IVF babies. I’m an IVF baby, and it’s a sore subject because my mom tried so hard to have a baby with my dad and it wasn’t until she tried IVF that she had me.
Stupidly, I asked him what he had against IVF babies. He immediately spews on and on that IVF babies are nothing more than objects of status to their parents, that it violates the rights of the child, depriving them of their true relationship with their parents, and can hinder the maturing of personality, etc.
By this point, I was done with the date and just nodded along to whatever he said. After he paid the check, he drove me home and walked me to the front door. I unlocked it and then turned around to say good night when he leaned in with his tongue already out. I didn’t know what to do so I tilted my head so he would hit my cheek.
Worst feeling ever of a tongue licking your face. When I went inside, he looked at me, shocked, and asked if I was going to invite him in. When I told him no, he got ticked and said that, “I paid for your freaking dinner!” By then, I just wanted to drink a bottle of wine by myself, so I took $10 out of my wallet, threw it in his face, and closed the door.
41. Well, That Stinks
I was chatting with this girl online and she was fairly good-looking. She was a cute, petite blonde. She was maybe 23, and I was probably 24 or so. She had a thin body with small breasts. She even sent me some sensual pics, alluded to light bondage, and seemed like she was up for whatever.
When we met, she looked just like her pic. I was happy to meet her, but there were some red flags: She started saying girlfriend-y stuff right away. She mentioned Valentine’s day, as if we were absolutely necessarily going to spend it together. BTW, she was a Ph.D. candidate in biology at a prestigious U.S. university.
Anyway, she seemed to be a little bit promiscuous, mentioning that she did it with a lot of her lab partners. That was all fine with me. What wasn’t fine was her breath. She had acute halitosis. We went back to her place where she started playing with handcuffs and such. However, I couldn’t get over her breath.
She was in just her panties, and I was probably half-naked myself, and I started to realize that my member wasn’t going to get hard. I had to make a choice about telling her that I had a bad case of nerves, or that her breath was unbearable. I gave her a line about not being over my ex, and that it just didn’t feel right yet. She was offended, started to cry, and kicked me out.
42. Getting Unlucky
Well, it wasn’t really a “blind” date, as I had seen photos, but on my first date with someone I met online, I reached into my pocket to pay for dinner and a strip of condoms fell out of my pocket. It landed right there on the floor between us. And it wasn’t like it fell out of my wallet…it was obvious that I had hastily shoved the brand new condoms in my pocket right before the date.
It was very clearly as if I was expecting to get it on that date. I was pretty embarrassed, and for the rest of the night felt like a jerk. I figured the cause was lost. We ended up going out for like a year, though, and it was funny in retrospect. Not at the time, though.
43. Dealings with the Devil
I met a seemingly nice girl on Tinder. We dated for 2 months. It was 2 months of pure torment. After the 3rd date, she started telling me things about myself that no one could ever know. The kind of secrets that one would bring to the grave. I pressured her and asked her how she knew. She finally admitted that she practiced black magic.
In the following weeks, she threatened to blackmail me, cursed my entire family even though they did nothing, got paranoid and accused me of cheating when I spent most of my time driving for work, and demanded relations whenever she wanted—even when she was angry. Once time, her voice changed to something screechy and raspy and I think I might been sleeping with a demon.
I had enough and forced myself to break up with her after 2 months. Deactivated all my social media accounts and went off the radar for a while after that, until I found out that she had a new guy to mess around with.
44. Do You Like-Like Me?
I met a woman who I really hit it off with. There was no physical affection for maybe six months of just hanging out several times a week as friends. One night we got hammered and I spent the night. After that, we still hung out just as frequently, spent the night every time, and we pretty much acted as a couple—going out with friends, wedding dates, etc, etc. I had things that lived at her place.
After maybe 6 months of this, I found out on the other 2-3 nights each week we weren’t together, she was hooking up with randoms on Tinder. Apparently, even in your 40s, it’s necessary to have that “so, like, are you officially my girlfriend?” conversation that you had to have in 6th grade.
45. No Signs of a Threat
A cute girl from OkCupid offered to pick me up for our first date and we hung out with some of her friends at the mall. Then we went driving around town having a ton of fun, getting fast food, talking, stargazing, the works. She goes to drop me off and I wanted to kiss her. Things started getting a little heavy and she stops me just as we’re thinking of fooling around in her car. We cooled off, said our goodnights, and she left.
The next day I texted her and she didn’t respond. Later on in the night, she finally called me. It was the most terrifying phone call of my life. She sounded a little awkward, and blurted out, “Hey, I just wanted to tell you I had a great time last night. But I’m going to kill myself now so I wanted to say goodbye before I do it.” WHAT?! I frantically tried to call her back.
She didn’t answer. Eventually, after a few more tries, she picked up again. I’m yelling at her and she’s just responding to me like this is normal for her. “I’m sitting on top of a bridge right now. As soon as the train comes, I’m throwing myself in front of it.” She hangs up again. I’m freaked out.
The only thing I could think to do was call the authorities, so I did. The chief and I spent the whole night calling this girl, trying to figure out her whereabouts, and dispatching officers to find her. Luckily, we learned that no trains were running through the town that night, and an officer eventually picked her up walking on the street next to one of the train tracks. She was committed that night.
The last phone call I got from her was in the hospital. Her parents were furious at me because apparently, she “did this kind of thing all the time.” They were mad that I’d called the authorities and they wanted me to pay the medical bills. I obviously refused, they threatened to sue me, and I hung up. Never heard from any of them again. I was so traumatized from that incident that I didn’t do online dating for a couple years.
46. In the Pocket
Ever played billiards on a first date? Imagine everything going great with the date…until she decides to flirt by sneaking up on you from behind while you’re taking a shot. Before her flirt, you take the shot and as you lean back your head connects directly with her nose, breaking it. Yeah, good times.
47. Dinner & a Show
Drove 40 minutes for a date with a woman who didn’t have a car, but she seemed really nice. Everything was going well for the first 10 minutes, then her ex showed up at the bar and joined us. They fought in front of me for 40 minutes, and I was just really hungry and enjoying the show with my dinner. Turns out she cheated on him, and I spent the rest of the date talking to him. Super nice dude.
48. A Strong Push Out of the Closet
I went on a date with a woman who I met at a karaoke bar. We met for tea, which was really uncomfortable because I didn’t know what kind of tea to order on a date, so I got chamomile to soothe my nerves. She talked a lot—I mean a lot. About her cats, the mean person at work, and her favorite brand of toothpaste. I could deal with all that—but what she said next just blew my mind.
Eventually, she told me that she had a tattoo above her posterior of an arrow pointing downwards and the words “EXIT ONLY.” I blinked, asked her why she would get a tattoo of that, and then moved a small step towards the journey of accepting my own gender preferences. I came out as gay two years later.
49. Sacrifice of the Night
I met this girl who was an aspiring model. I was really excited about meeting her. On our first date, she invited me over for dinner and a movie. When we sat down to watch the movie she stopped and told me she could see the colors of my aura. Now, I have known her for all of 45 minutes and she says that her aura matches with my aura and we will be getting married.
I’m 24 years old and freaking out. But being 24 and she being really hot I stayed. Later, she invites me to see her room and I notice this table with all these candles and strange things on it. I ask her about it, and she tells me she is a witch who can cast spells. Then she started talking really strangely about how she is a virgin and she wants to make sacrifices.
When she left the room, I went out the back door and jumped her fence and got to my car and drove as fast as I could. Thank God the date wasn’t at my house.
50. Footing the Bill
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.
51. Two’s a Crowd
Met up with a guy from OkCupid. I had mentioned I was into hockey while we were messaging, so he asked me out to watch a game at a bar and then grab dinner. He was cute, I liked the banter we had going, so I said sure. He picks a super crowded sports bar (not ideal for a date but we were supposed to watch a game so that makes sense) except it’s so crowded it’s insane. You could barely get in the door.
He arrived 10 minutes late, and then sat at the one empty seat at the bar while I awkwardly stood at his shoulder, trying to flag down the bartender. He got himself a beer, didn’t think to get me one. After about 15 minutes of this, I suggest we just go ahead and get dinner somewhere where I know they have TVs and it will be less crowded.
He offers to drive us over to the place I suggested, so I get in his car (NEVER DO THIS! THIS WAS DUMB!!) and it’s absolutely disgusting. There were at least a dozen empty energy drink cans all over the floor where I was trying to put my feet. The drink holder thing was filled with smoke butts…why would he offer to drive me when his car was this gross?! We could have driven separately!!
We get to the restaurant and he insists on a two-top table right next to the big window at the front of the place. Over the course of the 42 minutes we were in this restaurant, he went outside to smoke SEVEN TIMES. Each time he would stand on the other side of the big window and just look down at me. Just staring at me intensely while puffing away out there. It was awful.
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 sneakily takes 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?
53. Dodged a Brainwash
On my first date with a guy I met on an Internet dating site, he took me to the Scientology museum in London. I thought it was a unique date, and that it would make it easy to find things to talk about or laugh about. Nope. He proceeded to read every single piece of writing on every single exhibit. He also asked the attendant very probing questions about how one goes about joining Scientology, visibly sweating throughout the conversation.
Once we were done there, we went for a glass of wine and he told me he used to do a lot of hard substances. I was out of there like a shot.
54. To Catch My Heart
I went out to the movies with a girl on Valentine’s day, and it was going well. Afterward, as we were getting ready to call it a night, she wanted to go for a quick visit to a gift shop. We went to a nice one nearby, and I bought a few greeting cards while she just browsed. When it came time to pay, I paid for my cards and was getting ready to leave.
The cashier asked me if I wanted to buy anything else, and I said no. Then he asked my date, “Is there something you want to buy, Miss?” I looked back and forth between them, confused. She said no, but he asked again, “Are you sure?” She said she was sure. The cashier got this really intent look on his face—and suddenly, everything unraveled.
The cashier shouted “NOW!” and five of the staff surrounded us like a scene from a movie. The girl apparently was a kleptomaniac and had stuffed lots of gifts in her pants and bra. They had electronic surveillance and had caught it all on tape. The cashier threatened to call the authorities on the girl, but told me I could leave, as he could see I had no idea what was going on.
I decided to help the girl out and ended up buying all the stuff she had stolen to get her out of getting busted and her parents finding out.
55. Cruel Intentions
So I went on a couple of dates with this girl, and she was giving me some signs that she was ready to get a little physical. So I leaned in close and tried to kiss her, only to have her turn her face away from me. Stunned, I ended up going home and thinking it was over between us, but later on, she contacted me and wanted to go out again. I decided to go for it.
Again, after getting some heavy hints from her, I leaned in to kiss her—and she pushed me away again. So then I just flat-out asked what was going on. She straight-up tells me “I’m dating you so I can feel desirable, but I’m not attracted to you.” She called me the next day wanting to go out, and I told her I wasn’t dating people who made me feel undesirable, then hung up.
56. Let Down
I met this guy online and he kept bugging me to take me out to dinner. I finally agreed and he said he wanted to take me “somewhere nice.” We agreed to meet in a well-lit grocery store parking lot and then ride to the restaurant in his car. It was cool out, so I had put on a dress and tights and high-heeled boots. He pulled up in a Mercedes, and I suddenly wondered if I was dressed well enough for wherever we were going.
Now, I don’t know about any of you, but when I hear “somewhere nice,” it means a place that involves wait staff and tablecloths. We did the greetings and I got in his car and he drove us across the parking lot – to the Taco Bell drive-thru. I am not joking. I texted my teenage daughter from his car and she told me that things like that only happen in the movies. Needless to say, there was no second date.
57. Keep Your Pants on
My freshman year of college, I met this amazing, cute guy on the bus. We talked until I had to get off. A few weeks later, he came up as a suggested friend on Facebook. I added him, and we decided to meet up for tea. He showed up dressed in a full suit, and then proceeded to take me to a computer lab on campus…where he made us tea in a microwave.
He talked the entire time about how he was a nude model, and therefore was really good at sitting still?? He then demonstrated this by sitting still without moving for about 30 minutes, not looking at me, as I struggled to talk to him. Two weeks later, I cut through a building on campus and saw some, um, suggestive paintings of his entire body. We never went out again.
In University, I was interested in a gorgeous woman in one of my classes. Every time I saw her, I’d flirt shamelessly, so I was elated when she asked me out. She said we were going to see some live music. I went. I was in for a nasty surprise. She had taken me to a born again Christian conversion ambush group. They were singing songs though, so I stayed until the end.
59. Better Than a Toothache! Or…Not
A guy I had met three days previously offered to pick me up so we could hang out. I was cool with that, until he ended up dragging me around on errands. We even went to his dentist appointment. When I said I wanted to go home, he said he’d give me a ride, but only in exchange for oral favors. I got out right there and walked to a bus stop.
60. On a Break
I had been single for around nine months and resorted to chatrooms to see if I could meet a girl in my city. I started chatting with this girl who sounded great: same age, friendly, brown hair, green eyes, curves in the right places, does some modeling. Sweet! She doesn’t want to send me a pic for privacy reasons or whatever (should’ve heard alarm bells).
So, we decide to meet downtown for dinner. Hmm, she sure is a bit short and chubby for a model! Never mind, she seems nice in person so we go to dinner. The small talk was pretty average and the whole time she is looking around nervously. I finally ask her what’s wrong. She says, “Oh nothing, I’m just worried that my boyfriend might walk past and see us.” WTF?!!
Sensing my shock, she tries to appease me by saying, “We’ve been together for a couple years, but really it’s been over for a few months now. I just haven’t worked up the courage to dump him yet.” Right there I was so tempted to go to the bathroom and never come back. I decided to be a gentleman instead. We finished our dinner and I walked her to the train station. She called and emailed me a few times afterward, but I just ignored her. Surely, she knew the reason why.
61. 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…
62. Hot 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 metal music 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.
63. Mystery Date
Well, I’ve never personally gone on a blind date, but my friend accidentally set himself up with one. So, I’m going to call my friend Steve. Steve and I worked together at this retail store probably four years back, and we happened to work with this one girl roughly our age. She was cute, kind of tall, and fairly shy.
Anyway, fast forward four years. Steve had moved away for a year, then moved back home. He had been home for roughly 1.5 years, had no job or anything of the sort. He was in the store we used to work at one day and saw that this cute girl was still working there. Now he couldn’t remember her name. He sent me a pic of her and I recognized her, but again didn’t know her name.
Our original plan was myself, my gf, one of her friends, and my friend Steve were going to go see Toy Story 3. So, he decides he’s going to call up this girl who’s working and invite her out. He calls her up, talks to a manager, and finds out the girl working is called Tara (not her real name). So, he invites her out, and shockingly enough she agrees!
So, my friend Steve is all pumped, as it’s been literally years since he’s had a gf, and he calls me up and tells me about it. On my way into town I decide to stop in the store with my gf to walk by and see who’s working. Well…we either thought he asked out the wrong girl, or she was on break. We wandered around and couldn’t find her. So, we left, broke the news to Steve that his date might not be “as advertised.”
Regardless, 9:30 rolls around and we’re at the theatre. I’m buying tickets, and Steve wanders over and asks me what he’s supposed to do. Buy her a ticket and wait or what. I was so confused—but then I turned around and suddenly realized the hilarious truth. I see the girl who was working at the store…the WRONG girl. She’s quite a bit uglier than the girl he was aiming for, but ya…So, my gf and I just kind of quietly say, “Oh dang!” We break the news to him, and as we’re breaking the news she’s talking to the ticket guy, who’s only about 5 feet away.
She has no idea what he looks like, and they actually walked past each other without even noticing. So here they are, five feet apart, talking to their respective friends. She’s explaining to her friend that some random guy called her up on a date, and she didn’t know what to do, and my friend’s trying to figure out if he should introduce himself or not.
Amway’s, he ends up introducing himself, buys her the ticket…and shockingly enough they are around one month into their relationship now.
64. 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. Then everything went wrong. After one too many drinks, I projectile vomit on both the women. I immediately turn around, beeline it for the door, and walk back to the other side of campus where I played Guitar Hero for a bit, and then I passed out. Good times.
65. 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.
66. 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.
67. 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.
68. Do the Louis
I met a couple through a mutual friend and we hung out for a bit one night, had a decent time. I spent a couple days afterward texting back and forth with the wife of the couple, thinking hey, new friend. She eventually starts talking up this friend of hers, Gary, and it is clear she wants to set us up on a date. Okay, I think, I’m newly single again after five years of a bad relationship, we’ll see how this goes.
She describes him as “football player build”—not being a sports person, does not occur to me I should have asked her to clarify (would he be a quarterback or lineman, for instance). Anyhow, I meet Gary for coffee downtown. Suffice it to say, he is a substantial man. But I think hey, I’m not perfect either, I’ll give him a shot. We have an okay time over coffee, talking about regular random small talk topics.
He walks me back to my place, but the night is still young and he suggests hanging out and watching some Futurama. So, I invite him up. As soon as we are sitting down, he starts talking about his ex and all the drama she brought into his life, and it slowly comes to light that they may not be actually broken up, he is just “seeing what else is out there.”
Hm. At this point I’m more than over the date and am ready for him to get out of my apartment—so I go to the restroom and plan on feigning illness upon my return. Little did I realize, this night was about to take a horrifying turn: I return from the bathroom only to find him on my couch, touching himself furiously.
I freak out, ask him what he is doing, and he says, “What does it look like?” and makes a motion for me to come join him. I was kind of at a loss at this point, and I think all I did was say something about how he needs to leave. He removes his hand from inside his pants (did I mention he was wearing sweat pants? ick), shrugs, and exits. I never heard from him OR the woman who introduced me to him again.
69. Car Pharmacy
I agreed to a date with a guy I met online. He came to get me and seemed a bit weird, but I try not to judge people by their appearance. I had planned an evening of tea and movies, but he said he’d rather go to this party that his friend was having. I am very polite and I was trying to be open-minded, so I said yes. I regretted this almost immediately.
As soon as I got into his car, I noticed a funky smell. Then as he was driving, he pulled out bag of pills while explaining to me that he made his own version of a popular street substance. I politely declined, but he told me that if I didn’t want to try that, he had other things. I then saw the collection of substances in his car. But it didn’t end there.
Because I felt too awkward not to, I went to the party then an after-party, feeling trapped and extremely anxious the entire time. He dropped me off home later—and asked if he could have any of my medication. I awkwardly said no, and then gave up on love.
70. Maybe They Were Moving?
There was a guy who had been asking me to hang out for a while, but I had always said no because I got a weird vibe from him. He didn’t give up though, so I finally said yes, more to shut him up than anything else. He wanted me to go hang out at his house with his roommates, so I went. He then took me into the basement…where there was a dirty mattress on the floor, and nothing else.
I ran. To this day I have no idea what it was about, but I ran and never told anyone about it.
71. Stars In Mom’s Eyes
In the ninth grade, I agreed to a date with a guy from school. His mom drove us to the movies, and we had a pretty good time. When we got back though, everything changed for the worse. His mom started crying and saying he was going to be a big football star and that I was a gold digger just trying to capitalize on his success.
He was only on the school’s ninth grade team, but she clearly thought the NFL was a guarantee. They had a family meeting. When my sister arrived to pick me up, they wouldn’t let me leave the room until my status as a non-gold digger was verified.
72. A Family Affair
I had been friends with this guy for a couple months, and one weekend at a party we kissed. He was a nice guy, but a terrible kisser. He asked me on a date to go to an art gallery, and I thought that sounded really cool, so I said yes. What he failed to mention was that his entire family would be there—parents, siblings, grandparents, etc.
It was painfully awkward, to say the least. He invited me to have dinner with them, but I made my excuses and left, and said I had plans that night as well. Later, he showed up, uninvited and alone, to the party I was at that night. Creeped me out.
73. The Ol’ Switcheroo
I had just come back home from college and was having a night drinking at the local watering hole when I noticed the place had a new bartender. New attractive bartender. Short hair, nice tattoos that were clearly leading to interesting places and an Electric Six shirt. Oh. Yes. So, I start making a bit of conversation, and much to my surprise, we seem to really hit it off.
This wasn’t just a bartender-is-everyone’s-best-friend-until-they-leave hitting it off, but a really cool conversation. She starts hinting at if I’m seeing anyone, and I say no, and she immediately reaches into her pocket and starts writing something down. “On top is the number at the apartment, and these are directions. We’re having a party on Wednesday night, and you should come.”
True enough, a phone number and directions. What would you think? Wednesday comes and I’m dressed up and ready to impress. I head over to her place, knock on the door, and there she is, looking amazing. She smiles and hugs me, grabs me by the hand, and drags me through the party until she gets to this big dude. “Jonas, this is my roommate Jeff. Jeff, this is Jonas.”
I do the whole pleasantry thing, but when I turn around, she’s gone. Like Batman, she got outta there. Not knowing anyone else, I just keep on talking to Jeff. Seems like a good guy. Then it finally hit me. Suddenly he stops me mid-sentence and says, “You’re not gay, are you?” “No?” “You should really tell Liz that.” She had apparently set up the entire party as an excuse to hook me up with her roommate.
I had been on a blind date with a dude and didn’t even know.
74. 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.
75. 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.
76. 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.
77. 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.
78. The Cheap Hotel
I met this guy online. His wife had supposedly passed 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.
79. Chivalry? Nah
Sister’s husband wants me to go out with his best friend. Not so much blind, because we both had kinda known each other through him, but hadn’t ever talked exclusively among ourselves. First, he insists on opening doors for me. Not, like, the car door or a building door, that would have been okay. But everything.
When we pulled up to the movie theater, I tried to exit the car. Instead, he yelled, “NO, NO,” and ran out of the car and to the passenger side, pushed the door closed, and then opened it again. He took me to see Exit Wounds. Again, he made a scene at the box office when I said I’d pay for my own ticket. I had told him before that I thought first dates should be Dutch so that no one feels any undue pressure.
But he actually pushed me out of the way so he could pay for our tickets. I was steamed. After the movie, he asked if I wanted to go to Dunkin’ Donuts for coffee and dessert. I told him I had to get home. On the way home, he told me that he’d be really happy if I came to church with him on Sunday so I could meet his family. Ick.
80. Eating Buddies
A coworker introduced me to a friend of hers after going on about how much we had in common. I finally agreed one day to go on a date with her and off we went. We went out to eat at what was apparently her favorite restaurant. She was attractive, very smart, pretty funny, and seemed to be interested in me. It was a solid date.
We start texting one night to plan the second date, and she wants to go out to the same restaurant again. I ask if she’d like to do something else, like maybe ice skating or the science center, and she said, “As long as we can go out to eat first.” Thought this was weird, but okay. I asked if she’d like me to pick her up this time, as we had simply met there previously.
She responds with, “I don’t think my boyfriend would like that.” Wait…what? This led to a very awkward conversation over the phone. Apparently, she saw nothing wrong with going on dates with me, but didn’t want to do anything “romantic.” I asked her why she didn’t tell me this information from the beginning and she said she didn’t think it was a big deal.
Eventually, she admitted that she wanted someone to take her out because her “boyfriend never feeds her.” I told her it wasn’t going to work out and she actually asked, “Are we still going out to eat?” About a month after that, after neither of us had spoken to other, she randomly texted me again asking if I wanted to go out to eat again.
81. Right Sentiment, Wrong Time
The first words out of her mouth were, “I just want you to know, I really hate patriarchy.” Not even a hello.
Waited for her at the theater for two hours. She shows up drunk. Watched a terrible movie, just whatever was about to start. She took me to a bar afterward. Ended up being a gay bar and she tried to get me to admit I was gay. I flirted with the gay bartender to make the night less awful.
83. Every Man’s Dream
My SO said he had a Match date where the woman got incredibly drunk, and as they were walking back to his car so he could drive her home, she asked him to “wait right here.” He thought maybe she was making a phone call or had to throw up, because she walked into an alley. Then she spread her legs and began peeing from under her skirt, spraying all over her legs and the wall of the alley, after which she called to him in a drunken slur, “Is this turning you on?”
There was no second date, and he scrubbed out his car seat with Mr. Clean.
84. All Over It
I met a girl from Tinder and we saw each other a few times. She had an ex that she still talked to, but hadn’t had any feelings for in a few years. So, I go to her apartment and this place is like a shrine to him with pictures of him on every wall. And it wasn’t just from when they were together and she never took them down.
She just moved to this place a month prior so she recently decorated her apartment with his face. It really creeped me out and felt like I was going to be some sort of sacrifice to get him back.
85. 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 authorities 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, um, activities.
86. 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.
87. 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.
88. 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.
89. 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.
90. 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.
91. 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.
92. Ok, Happy Gilmore
My wife told me about a date she went on once with a guy who turned up in shorts and flip flops on a rainy day in November. When she asked him if he was cold, he said “Nope, I have no feeling in my feet. Look!” He proceeded to stab himself in the foot with his umbrella while repeatedly asking her if she “wanted a go.”
93. Three’s a Crowd
Went to pick a girl up at her house after meeting her on a dating website. She seemed significantly larger than her photo, but only in the lower abdominal region. This is when I realized that she had failed to mention that she was pregnant.
94. Argh, Matey
I was 16 years old when I scored a date with an 18-year-old girl. I really, really liked this girl, so of course I was extremely nervous. It was also my first date ever. I took her out to eat, and then we went to see the second Mummy movie. Everything was going great, I even had my arm around her and all that jazz.
Then, during the pigmy chase scene, one of those dudes popped up and made me jump. My arm was still around her—and somehow, my finger went straight into her eye. In fact, I had not only poked, but had actually scratched this poor girl’s eye. Our date ended because she had to go to the ER. But that wasn’t even the worst part.
To make matters even more humiliating for me, she then had to wear an eye patch for weeks. So, during the first date I ever went on, I turned the girl into a pirate.
95. Method Actor?
I went out with a guy for a pizza date. Or so I thought. As we were sitting eating our pizza, he suddenly put on a clown nose out of nowhere, and then just kept eating. I asked him if there was an explanation to that, and he said he was “just trying out his new nose.” Then he started jazz scatting like he was Ella Fitzgerald. For two hours, he was just jammin’ to himself in a pizza place with a clown nose.
I didn’t want to leave because I was his ride back to the train station, and because he had traveled pretty far to see me. Eventually, I drove him back to the train station. He didn’t get out of my car. I asked him why, and he said, “I’m thinking.” Then he leaned in like he was going to kiss me—but instead rubbed his face on mine like a cat, licked my cheek, and left. Of all of my bad dates, none have ever left me more confused than that one.
A guy I worked with kept asking me out, but I continuously said no. After about a year, I started to feel bad for the guy and finally said yes to a date. He asked me to lunch, so I figured it could be a quick, easy “date.” He picked me up. Then he took me to Wendy’s. Then he made me order off the dollar menu. I also had a limit of two items.
After a very quiet lunch, during which he hunkered over his chicken nuggets like he was afraid I’d take one, he said he needed to stop at Walmart. We went in and he headed to the lotion section. He then grabbed two scented lotions and asked which one I liked better. Trying to be nice, I picked one. He responded with one of the most horrifying sentences I’ve ever heard.
“Great! I’ll use this for your massage!” Luckily, I had to work in two hours, so I had an excuse to tell him the massage would have to wait. I spent the next three months trying to avoid him until he quit.
97. Wrong Answer
I had a guy take me to a Beer n’ Christ show. He was an extremely strict Catholic and thought I could benefit from letting Christ into my cold, cold, cold, Jewish heart. So I went. I was open-minded; I’m only half-Jewish and have always been interested in other religions. It was going okay…until the priest told us a hypothetical tale of a brother who is paralyzed.
He asked, “How many of you here would purchase stem cells if they could allow your brother to walk again?” My hand shot up. I looked around the room… and realized I’d answered incorrectly. No other hands. Everybody was staring at me, including my date and the priest. I was ‘blessed out’ like nobody’s business and was told I was an embarrassment to my date.
98. 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.”
98. The Oedipal Deal
It ended up being a double date with his mom and her OkCupid date. He told me that he and his mom were a “package deal.” I was mortified. There was no second date.
99. Taking the Term “Blind Date” a Little Too Far
It was a blind date. I got there first and told him where I was sitting. I actually saw him take one look at me and suddenly hang up his phone and walk back to his car. I know I should have understood the situation immediately, but I was in total denial. I tried to call him back, thinking something must have happened, and he didn’t answer. No more answers to calls or texts afterward. That one really hurt.
100. Doo-doo Dude
My sister’s friend met this guy on Tinder and went for dinner. They hit it off really well and he invited her back to his place. She really liked the dude so went with it, and things were getting hot when she started getting this horrible feeling. She went to the bathroom and literally had explosive diarrhea and messed herself, all over her body, the full deal. She was completely mortified and then had to explain to this dude what happened.
The dude seemed really chill and told her to get a shower and go get changed into some of his clothes and not to worry and that he would clean it up and took her dirty clothes away. It seemed like the crisis was averted—but then she stepped out of the bathroom, and was greeting by a truly horrifying sight. He was wearing her poop covered clothes and covering himself in the poop. She ran out the house in just a towel and called the authorities.
It turns out he was into that kind of thing. At one point on the dinner date when she went to the toilet, he had spiked her drink with something to intentionally poop herself.
101. A Tale of Two Roommates
I was having a girl over and it was my first time dating in many years. My female roommate who I am super close with was there as well and knew all about my situation. When I left the room for a brief moment, I accidentally overheard my roommate say “I know he’s shy and a little awkward at first, but give it a shot! He’s super sweet and really funny once he’s comfortable, and he’s definitely worth the effort!” Hearing that gave me a huge and much-needed boost, especially since I struggle with confidence and usually don’t like myself. Thanks, roomie. I owe you one!