Dating Nightmares: People Share Their Horror Stories From The Worst Dates Imaginable
Nobody ever said dating was easy, but nobody ever said it was supposed to be this hard! From crazies to creeps, the people of the internet have been on every kind of bad date imaginable—and we’ve collected their most insane stories here for your enjoyment.
#1 When You Gotta Go, You Gotta Go. Hard.
20-year-old me went out to dinner to meet her family for the first time. Got dressed up in nice khakis and a sweater. In the middle I farted but ended up pooping my pants with liquid death. There was no hiding the smell, as well as the HUGE FREAKING STAIN ON MY PANTS. It was awkward for all those involved.
#2 The Rank Smell of Rejection
A guy got stood up. He then drank a magnum bottle of red wine (8 glasses of wine) and ate three apps out of depression. His date called him, and he started cussing her out. He asked for more wine and then I had to cut him off. So he got up and tried to run out of the restaurant with a bottle he grabbed from a rack. An off-duty cop tackled him in the lobby, and then he pooped his pants in front of everyone waiting for a table. He lied there screaming with the guy holding him down until the cops arrived and arrested him. This is my fondest memory of being a bartender at Olive Garden.
#3 How NOT To Act On A First Date
I met this guy because he was staying with one of my friends. His family had recently kicked him out. He was cute, and I thought that a date would raise his spirits. However, the entire date he talked about his favorite violent criminals, which of them he thought were attractive, the mistakes they did that got them caught, and how he would end someone if he just had enough courage to.
He kept on bragging that he knew the perfect way to end and get away with it. Half way through the date, I got sick. I was glad to call it off at that point. After the date, he told everyone that would listen terrible things about me that were not even true. My friend kicked him out soon after, and I do not know where he is now.
#4 Crappy Time
Took a chance on a questionable fart when she was in the bathroom. Crapped myself.
#5 Who Was This One Bad For, You or Them?
I threw up onto their shoes and then continued to drink more.
#6 I Think This Counts as an Emergency Worth Escaping
I was bartending in NY and watched this couple who had met on Tinder have their first date sitting at my bar. The girl was a complete maniac. Kept bringing up the fact that the dude she was with could be a psychopath and could murder her (he had given no indication of this) and went on Tinder while he was still sitting beside her at the bar.
She kept telling him he was lucky that she agreed to meet him at all, and she didn’t think he’d be this boring. She ordered about 5 or 6 LITs and several shots, he literally just had two beers. She made him pay for everything. My favorite part was that he excused himself to go to the bathroom and left through the fire escape. Absolutely brilliant. To be clear, there was only one official entrance and exit. This dude escaped out the back and she went searching for him. Straight up thought he had disappeared out of the bar.
#7 Getting It All Out On The Table
Met girl on Match. She showed up 20 minutes late. I had to “excuse myself” so I could hide out in the bathroom and write down as much of the crazy things this woman was saying before I forgot.
Topics included, but were not limited to: Daddy issues, her mother loves her brother more, miscarriage, being married before, when “we” start dating, when “we” are married, setting me up with her assistant, how she’ll “screw me with blood on my face,” things she does when she’s high, Brazilian trance music, adopting children, what’s my dog’s name again, how she doesn’t trust animated movies, why she was 20 minutes late, owning a business, when it’s acceptable to use the c-word, being a vegetarian, her blind cat, her dying uncle, abusive relationships, the city of Tampa, free-range urination, and can we order tater tots. We didn’t go out again.
#8 Flirting With Rage
Finally get to share this story! A couple of years ago I dabbled a bit with Tinder. Met one guy who was super cute, traveled a lot, and seemed interesting. I suppose “interesting” was one word I could use to describe him. We start the date by getting lunch and a few beers at my favorite spot in town. We were chatting away and the topic of daydreaming came up. I asked him what he daydreamed about.
His eyes then get a bit dark and his voice gets low as he says, “When I daydream, I imagine the light leaving my enemy’s eyes.” By this point I was a few beers in and didn’t know what to say. I respond with, “Oh…so uh, how do you do it?” He looks away, ponders for a second and says, “Harpoon.” The rest of the date was spent with him talking to me about his extensive anger issues and how he still lives and sleeps with his ex. Heck, he had just slept with her before he came to meet up with me. That was when I decided to stop using Tinder.
#9 Cat Conversation
It was a speed date. He talked about his dead cats, all of them from his past, for the entire five minutes or whatever. I’m not sure he knew my name.
#10 Dud Date
I went on a date one time when I was in elementary school with a girl I met through a girl in my class. We were going to see Grease, (the 20th anniversary release in 1998) and we had a lot of time to end before the movie started. Being the adventurous young chap that I was, I decided to get some Milk Duds from the snack counter, as I had never eaten them before.
I thought, “Milk chocolate? Caramel? I love both of them, so together, they should be amazing!” I had a few of them, and they were pretty good. I waited for them to melt, then chomped down and ate them. After a few, however, I became impatient of waiting for them to soften up and started to just bite through them. It was a little challenging biting through solid caramel, but nothing terrible.
However, one Milk Dud was more difficult to chew than the rest. I popped this particular one to the back of my mouth, and the caramel core decided to latch itself onto one of my molars. I pulled and pulled to try to get it unstuck from my teeth, but the caramel was too much for my young teeth. In trying to open up my mouth, I ended up ripping the stuck molar from my mouth with the hard Milk Dud still attached. The molar wasn’t even loose, it just got pulled out!
It’s strange enough going on dates when you’re that young. It’s a lot stranger when it’s with a girl you met only once prior to the date. It’s by far the strangest when you end up ripping out a not-loose tooth with a Milk Dud still attached, and then have to sit through Grease. I should note: I have not eaten a Milk Dud since.
#11 Glitch In The Dating Matrix
It was my second date with this guy, and he said the exact same things that he said on the first date. Word for word. The same stories, the same “random thoughts,” the same questions…It freaked me out so much that at first I played along and answered in the exact same way, as though we were both following some weird script. Eventually, I tried to break the mold and ask him new things, but he would just bring it back around to the same topics as last time. It was like I was in a computer program and there was a glitch. Still freaks me out to think of it.
#12 Unmasking the Facade
It was less of a date and more of a hookup. Very handsome dude. I made my intentions clear and asked him what he was interested in. “Firefighting, hooking up, and fighting.” Yeah, tough guy, let’s meet for drinks and go back to your place! Have drinks, going well. Go back to his place and have more drinks, still going well. Start getting down to business and, when we’re both nearly completely undressed, he pulls away. Quickly dress and run out the door with a pat on his head while he cries about his ex-girlfriend. He was not ready for a hook up.
#13 Ending the Date
I was driving to the movies on a first date with a smoking hot girl and we saw a feral cat get destroyed in traffic. The poor thing got a paw run over first and it was doing this crazy leaping thing and people WERE NOT STOPPING and then a truck finished it.
Game over, date finished, we went and sat on her couch for an hour and then I went home.
Poor little cat.
#14 Love Slap
I took a girl who I really liked on a first date to the movies. The movies were probably a bad choice because I couldn’t take my eyes off her. During the movie, I noticed she had a piece of hair hanging down in front of her face. Me, being the gentlemen that I am, saw this as an opportunity to be cute and go in for the kiss.
Screw me, was I ever wrong…I thought to myself, “I’ll reach over and move her hair out of her face which will then lead into the kiss and it’ll be cute.” So, I lean in and reach over to move the hair from her face and make my ‘smooth move’….and as my hand got to within 6 inches of the target zone she comes out of absolutely nowhere, reaches up, and moves the freaking hair herself!!
Damn…So at this point, I’m 90% committed, hand located somewhere in front of her face, with no clear objective, and not to mention, obviously blocking her view of the movie. I immediately become nervous and I’m having second thoughts about my decision, but I’m a committed and confident guy who doesn’t back down from a challenge.
But at that moment, all logic froze, and my cute plan dissolved. There was no purpose for my hand anymore, yet it was still on a collision course with her face and for some reason, I couldn’t stop it. I reached over and wiped her forehead, taking whatever makeup that was there with me. Leaving her with an obvious stripe on her forehead that was most noticeable during the brighter scenes, lighting up the movie theatre.
She looked at me horrified. She didn’t even have it in her to ask me what the heck I was thinking because she was so shocked. My entire world turned to flames and the room got considerably hotter. And I didn’t get my cute first kiss. In fact, I got a deleted number…
15. My Fight in Shining Armor
Malicious compliance. First date with a dude. I told him I had a 3-hour window to hang out. He proceeded to suggest a coffee shop, but upon arrival told me he hated coffee and the atmosphere of coffee shops. Cool. So, I suggested an art museum or bowling. He said he brought no money because he doesn’t pay for dates on principle.
I offer to pay but he won’t have that either. So, I suggest a walk around a nearby lake. We have the most one-sided conversation of me asking questions and him giving one-word answers. When we got back to our cars (an hour later) I told him he didn’t really seem like he was into me and suggested we cut the “date” short.
The dude BLEW UP. “You said you had 3 hours and it’s only been an hour, you liar! You have 2 more hours! Our date is supposed to last 2 more hours.” Fine dude. It’s a beautiful day and if you want to do two more laps around the lake then by all means. I talked about any little tidbit that entered my brain, like the chick from HIMYM.
“Do you think when a porcupine walks through the woods his quills act like giant whiskers and he’s just constantly getting poked anytime he bumps into something? I ate a kiwi whole once and my mouth felt really fuzzy after, actually I ate a random leaf one time and my whole tongue swelled up let me tell you about that…”. I never heard from him again.
#16 He Did Say He Can’t Dance
Went dancing with a girl from work; first date with anyone, 25 years old—zero social skills, naturally. Wisely, I let her do all the talking, and we have a decent enough time. She doesn’t even seem to notice my awkwardness, and I start to loosen up and even show a bit of confidence. “Hey, this is sort of fun!” I say to myself.
I explain that I can’t dance, but she goads me into giving it a try—just one slow song. She’ll walk me through it, she says, no big deal. No one’s watching. My blood pressure shoots through the roof, but I’m still on a high, and hardly noticing my hands trembling and my pulse approaching a dangerous rate. We go over to the floor and she puts my hand on her waist and takes my other hand in hers.
Instantly, my breath leaves me and the room fills with pea soup fog. The arteries in my forearms and throat contract painfully and a crushing sensation overtakes me; fade to black. My memory cuts out at that point, but I’m told that I managed to crawl to the corner of the room after hitting the floor.
When I came to, I was completely numb and paralyzed from head to toe, gasping for breath, but getting almost none at all. The crushing feeling intensified and I lost consciousness several more times in the next hour or so as I lay in the corner. Eventually, I regained enough feeling in my legs to pull myself upright, stagger to a stool, and order an orange juice.
My scalp and tongue were still numb, but I managed to drink it down and gather my thoughts enough to remember where I was, what day it was, and how I had gotten there. In another hour I was aware enough to risk driving home, which I did as slowly and deliberately as I could with my still-dull reflexes and persisting numbness. I made it back to my room and slept until past noon the next day, still a bit numb and groggy even then. My date, I found out later, had been profoundly embarrassed by my actions, and left immediately after I fell. She forgave me and never mentioned it to anyone, as far as I know.
#17 Bad Decision
I was out one night, and had beyond enough to drink. I went to a cafe next door to the bar, grabbed some food and hung out for a while. This guy walks in. He’s kind of cute, so we start talking and I invited him to share my sweet potato fries with me. One thing led to another, we went outside, made out for a while and then we took a taxi back to my place.
Everything seemed fine until I tried to drop him off the next morning. I asked him where he lived, and he kind of avoided the question, just giving me directions. To the local homeless shelter. He was homeless. And he admitted he was homeless because he just got out of jail. For assaulting a woman. I had given him my number before any of that came out, and he called constantly. After a day, I had to block all unknown numbers on my phone, because (being homeless and all) he called from a different number every time. It was miserable, and it took nearly a month for the messages to stop (thank god for visual voicemail).
#18 Skull Over Heels in Love
I got way too tipsy, slipped and cracked my head open on his sink. I had no idea how bad I was hurt until I walked back into the party and everyone giggled at me in shock because I was covered in blood from where my eyebrow piercing had been ripped out. THEN he called his dad over to come stitch me up, his dad being a doctor. So that was a nice first meeting of my new boyfriend’s parent. I remember thinking “This guy is never going to ask me out again,” but he did. We dated for 4 years. 20-plus years later, we’re still friends. So, I guess it worked out ok in the end.
#19 Let’s Pay to Play Pretend
One of my first jobs in New York was managing a lounge/cocktail bar in a high-end hotel. At around 3 or 4 o’clock, a guy who looked pretty cheesy (slicked back hair, bad suit, etc.) came up to me and demanded that he get that window table tonight for his date (he had a reservation for 8pm). I explained to him that I can’t guarantee it etc. etc. and he slipped me $400 with the “How about now” look in which I eventually caved in and told him that I’d take care of it.
He then pulled another stack of hundreds and started counting them in front of me while asking if I could go a little extra by coming over to the table when he was there with the date and pretend that I knew him from a movie. At this point, if I’ve gone this far, why not? Sure enough, he rolled around later in the evening with a blonde bimbo, and after they’d had a glass of champagne, I approached the tables around them and checked on how they were doing before going over to him and did the whole “How are you enjoying your evening?”
And before walking off, I did an Oscar-worthy double take with an “Are.. are you… by any chance..? You must be..” at which point he had this douchey smile lapping up the “recognition” he was getting from this young dude he’d just paid off. Most importantly for him though, it worked—she was loving it—and they left shortly after, and he slipped me another $600 on the way out.
#20 Thanks, Che
Michael Che (comedian and anchor for SNL’s Weekend Update) ruined one of my first dates! I go to a lot of standup around NYC and I happened to see him trying out material at two different free shows in the same week. He was doing this crowd material bit about porn where he would pick a guy in the front row and corner them and ask them what they searched for when they looked for porn.
The first time I saw him doing it he just would not let up on this poor guy, the guy didn’t want to answer and kept saying “I don’t know” or “I’m not sure” but Che kept asking “come on, man, I KNOW you know. What do you mean you don’t know?” The guy never relented and said anything out loud but Che kept pressing him for seriously the entire show, like he kept going back to this one poor guy.
Cut to later in the week, I’m taking an OkCupid date to a standup show, I sit in the front and Michael Che turns out to be the surprise headliner. The second I see him on stage I know it’s gonna be me, I know he’s gonna do the bit again and I’m sitting front and center. My brain is racing trying to think of a good way to get out of this awkward situation, “don’t say BDSM don’t say BDSM” (this was a very casual date and I had not been speaking to this poor girl for very long plus I’m already a weirdo).
Within like 30 seconds he turns to me and asks “what about you, sir, what do you type in the search bar when you look for porn?” and I think “Okay self, just say the most innocuous harmless kink possible.” I stall for a second with a “who me?” and he repeats the question, so I blurt out without thinking “Redheads!” Whew, fine, I’m in the clear. Awkward situation handled.
I forgot that my date was a redhead. Of course he immediately picks up on that “you know the girl sitting next to you is a redhead right?” and I reply “yes, we are… actually… here on a date.” He said “wow, this has never happened to me during this bit before” then cut me some slack and moved on.
In the larger scheme of things this probably wasn’t that bad, and the date wasn’t going spectacularly anyway so it wasn’t like a huge loss, but it definitely made things very awkward for the rest of the evening. It was kind of a relief when she said no to a second date because then I immediately texted her back and was like “That’s fine OH MY GOD CAN WE TALK ABOUT HOW CRAZY AWKWARD THAT WAS?” and she was like “I KNOW!!”
#21 This Can’t Go Wrong in Any Way…
“I’m a recovering gambling addict, want to go to Vegas with me?”
#22 Try Google Translate Next Time
It’s not NSFW but it was darn terrible for a teenage boy to experience. Was hitting it off with this smoking hot French-speaking girl (the type they employ in nightclubs to dance in the cage or on the luminescent block), when out of the blue we stumbled into a friend of mine. The dude became somewhat a third wheel but actually managed to completely steal the girl away and they started kissing in front of me after roughly 45 minutes.
Here’s the bad part: dude didn’t speak a word of French, and they needed/requested me to tag along to translate for each other… Needless to say it didn’t take long for me to find a way out and spend the rest of my summer angry, humiliated, and depressed. Never saw or talked to either of them since.
#23 Twilight Times
I met a girl in a club whilst working as a nightlife photographer—you meet a lot of girls that way, it’s a good icebreaker. She was pretty, sweet and funny, and we kept bumping into each other throughout the night as I worked. Ended up finishing work and getting to chat to her a bit, things were great, and we ended up going back to her place for a bit of tipsy rumpy pumpy.
When we got into her room it was like a normal student room, posters on the wall etc, typical girl stuff, y’know? Twilightposter, calendar of a boy band, some frilly stuff… all that. Quite cute. Anyway, we got down to business, and we were nearly naked when she whispers into my ear in the most seductive way possible, “Bite me like Edward.” I had my clothes on and was out of the door faster than you could even imagine.
#24 A Cup of Sugar
During college, I took a girl I really liked to the movies for our first date. We were sitting there chatting during the pre-trailer commercials when the house lights are all still up. During this time, I start to fidget with the cup holder between us. At one point I mindlessly reach in and grab the little cross piece at the bottom and got my hand stuck.
She hadn’t noticed but there was no smooth way to extract my hand. I eventually had to ask her to turn around, which given that this was a first date was a really odd thing to do. I proceeded to use my other hand to yank my hand out of the cup holder, almost hitting her in the process. I was so awkward about it I just told her what happened, and she laughed hysterically at me.
We actually dated for a while. At one point during the relationship we were joking about the first date while waiting for another movie to start. And yes, in the course of pantomiming the story, I got my hand stuck in the cup holder again. I don’t reach in movie theater cupholders anymore.
#25 Dinner With a No Hit Wonder
I work at a dinner theater. We usually do proposals where we set up a “random draw” where the “winner” comes up on the stage to win their prize and are then surprised by their partner, who proposes. It’s usually sweet and makes everybody in the room all fuzzy and warm. This one guy wanted to take it further, and requested to perform a song—he brought his own music and everything. We’re pretty easy-going at this job, so we agree to let him do it.
We do the fake draw, the woman comes up on stage in front of a room of 400 people, and the music starts to play. Apparently, this guy was a little nervous, and he compensated by having a few drinks. So what follows is a slurred performance of a song written by this guy that seemed to focus on how he was sorry for cheating on this woman with her sister, and at the end of it, he gets down on one knee and proposes.
Usually this gets a round of applause, encouraging the person to say yes, but not after that train wreck of a performance. The poor woman was just holding her face the entire time and starts shaking her head and says, “No, what’s wrong with you?” She storms off and leaves him and our stage manager on stage to a bunch of murmuring from the audience. The only thing our stage manager can think of to say on mic is, “Well, that’s that.” The guy ended up staying for the rest of the show and had many more drinks. That was years ago, and it still remains one of the cringiest things I’ve ever seen.
#26 Wrong Side Of 24
In 2001 internet dating hadn’t really taken off here, so this happened as a result of a personals ad. I was newly single and feeling pretty frisky so took a chance on a “Mr. Wrong, 24, seeks Miss Right” ad. We corresponded and spoke on the phone before meeting an everything sounded ok.
I was misled quite badly. Paul was more like 48 than 24—a paunchy, pasty, bargain basement Freddie Mercury lookalike. Being of Italian heritage he was staunchly anti-racist but thought homophobia was fine. He got tipsy and wanted to take me to the circus. It was a really uncomfortable experience but I managed to escape with just one cheek having been slobbered on after he slurred “You’re really cute.”
#27 Worst Case, Bar None
I met a guy online. Can’t remember which site, but he scheduled the date at a bar—not even a restaurant, a BAR. A bar that didn’t even serve food. He was apparently a recovering alcoholic so he only ordered Cranberry juice, but he failed to tell me that until after I had already ordered a glass of wine. Why on EARTH would you invite someone to a BAR if you’re an addict? The entire thing was so bizarre to me, and on top of it he turned out to be a complete jerk.
He ended up leaving and wanted to walk me back to the metro and I basically said: “no thanks, I’ll stay here for a bit.” He was shocked and offended. I don’t fully know what he was thinking, but he finally left. When he left, the bartender immediately came over and was like, “Holy cow, that guy was a DOUCHE!” He took care of my tab and gave me another drink on the house. So there was at least a silver lining.
#28 Gambling on Attraction
I hadn’t had a terrible one til this summer. I met this dude from Tinder at a coffee shop and he immediately started talking about his professional gambling habits and putting his friends down (and mentioning they were fat).
He mentioned he’d need to move his car and I said I’d walk with him, figuring he’d drive it around the block from a nearby location. Nope, he’d parked his enormous white van—in which he told me he was currently sleeping—two miles away.
I walked him there and then abruptly left to go hang out with a friend in the area. To his credit, he texted later apologizing for creeping me out. I didn’t respond.
#29 Feeling Her Brains
I was to meet my girlfriend in a building near midnight for a date. When I got to the predesignated room in that building she directed my attention to a jar on the table. It had a human brain in it. She told me to don gloves and take the brain out of the jar. As I was holding the brain, it seemed very small. I asked, “Is this a child’s brain?” She said, “Yes.”
I felt a shiver run down my spine as I held the weight of the child’s brain in my hands. I started to imagine what this child was like before it died. What did its face look like? What kind of personality did it have? She interrupted what had become a rather chilling reflection by telling me I had to help her cut up the brain before midnight.
We cut into the flesh of the brain that used to hold memories, feelings and dreams. Now it was cold and lifeless as my date became very attentive to every detail of structure that our knife revealed as we cut the brain apart. When we finished, I put the pieces back into the jar and we left for the rest of our date. She was a medical student and I often had to help her study in our dates. It was the only date I ever had in which I felt genuinely ghoulish for part of the date.
#30 No Compliment in Comparison
Freshman year college: it wasn’t exactly a date, but I was flirting with this girl name Lindsey at a party and she was not into me at all. I kept trying to talk to her and she would flat out ignore me. So, I ended up talking to her friend Sarah and bringing her home. I used to live in the dorms and shared a room so we ended up laying in my tub so we could hookup.
Sarah stops kissing me and asks, “What do you think of Lindsey?” and with no hesitation say she’s gorgeous. She then asked what I thought of her and I paused like an idiot. Then I replied, “Oh, you’re pretty.” Sarah begins crying like crazy cause everyone was apparently into Lindsey. Then my roommate starts banging on the bathroom door cause she’s crying so loud and basically just kicks her out because he had work the next morning.
#31 What’s Your Number?
Saw an obvious first date where the lady was grilling the guy on how much money he makes. He didn’t really want to answer. It was awkward serving steak and salad during an interrogation.
#32 What Did You Expect From A Movie Titled “Happy Feet”
This was in high school, some girl from our rival school and I met, hit it off. She really wanted to see Happy Feet, the dancing penguin movie. Decide to take her, I like penguins anyways. I swear about half way through the movie she leans over to me and says, “Oh I get it, they’re dancing!” I thought she was trying to be cute, but she was serious. This movie was her idea, I figured she knew. The penguins were dancing for at least an hour before she said this to me. We lasted another week.
#33Think of This as a Learning Experience
I asked a girl in my class out on a date a few years ago, we had all the details set in stone, and I showed up to find out she invited the 30 other people from the class. I had to sit through an hour and a half of the “class lunch,” which she gave me credit for organizing, and pretend that I didn’t think it was gonna be a date the whole time. Ouch.
#34 Doggone It
Met on Tinder. I mentioned I wanted to see a band playing at the local fair, he suggested we go together. We met up there & he wanted to win me one of those teddy bears from a game, which was kind of sweet. He even told me I didn’t have to keep it and we could donate it (they have donation bins for stuffed animals all over the grounds). All was going fairly well actually. We watched the band & then he suggested buying me a couple drinks after.
As we are drinking & talking he just casually brought up that he deals illicit substances on the side, and that if it came between that and his dog, he would choose the illicit substances, and if his dog’s life ended over that then, “oh well.” I just stared in shock, as he seemed fairly normal up until this point. I changed the subject, we finished our drinks, and I went home. I did give him a second date, this time without booze involved just to be sure it wasn’t the booze talking. It was not the booze talking. There was no third date.
#35 Parental Pick Up
He called 20 minutes before he was supposed to pick me up. Told me he’d be a couple hours late because he wanted to play basketball… the time he was supposed to get me rolled around… no show… twenty minutes later a car pulls up and his mom gets out… (keep in mind we’re freshmen in college). He sent his parents to come get me. 20-minute drive to his house in the car. Alone with his parents. He proceeded to talk about the girl he was in love with for the rest of the date and ended it with an awkward hug stating that it wouldn’t work because we lived too far away.
#36 A Blast from the Past Should Have Been a Blast in the Face
About two years ago, I divorced my wife after she cheated with a guy she met at my mother’s funeral. Six months after the divorce, I’m on my first date with a girl named Heidi. She wanted to stop by a local tavern that was hosting a charity benefit. We did…Worst decision ever. I walk in the front door and immediately I am face to face with the guy who screwed my wife.
He and I grew up as friends but lost touch until he came to mom’s funeral. He attempted to say something to me, and I immediately cut him off and threatened him rather harshly. He left. I spent the next 30 minutes explaining what just happened to her. On the bright side, she totally got it and said I should have punched him…
#37 At Least He’s Moving on
Served a couple a few months ago. Every time I walked over, he would always be the one talking, and she would just be sitting there not having a good time. At the end, I asked if it was one bill or separate and she immediately piped up, “SEPARATE.” I go and take his payment, and as I hand over the debit machine to the girl, I see the guy take his phone out and start swiping through Tinder.
#38 More Than A Hike
Years ago, I met a girl online and after we’d approved of each other’s photos and list of interests, we talked on the phone and hit it off right away. She lived about an hour away, and she said she wanted to go to a local national park and go hiking and have a picnic. I get to her house to pick her up and see that she has packed a tent, sleeping bags, a cooler, and basically a full weekend worth of camping equipment. I told her I thought we were just going hiking and she said “I figured we could just camp out overnight. Just get me back home in time for church in the morning.”
So we head out, we set up the tent, go for a hike, swim in the lake, have dinner in the lodge, head back to the campsite, make a fire, and settle in for the night. Later, in the tent, stuff starts happening. After a while she says “Can we wait a bit on that, and just go to sleep.” I oblige and we sleep. In the early morning hours, she wakes me up by making it very clear the wait is over. After we finish, she starts crying. She apologizes and says she’s not ready to be in a relationship. I tell her I understand but I’m pretty confused by this point. We pack up everything and I drive her home and drop her off at her house.
About 15 minutes later, I get a call on my cell phone. It’s my dad. He asks “What the hell are you doing?” I tell him I have no idea what he’s talking about. He says “The Sheriff’s department just came by here looking for you and asking if I knew your whereabouts. You’re wanted in the disappearance of some girl. Her family said she never came home last night. They went to your place first but nobody was there.” Apparently, she wasn’t home for church and her family freaked out. I called her and told her to please contact the Sheriff and let them know she was not, in fact, kidnapped. She laughed and then called them. We never had a second date.
#39 Even Pleather Can’t Save You From This Threat
Getting bit by her on my arm so hard that it left mild teeth marks and a massive bruise, even through my thick pleather jacket.
#40 Not in the Family
This was the first official date I had with this girl. I was in the service and met her through a friend, but she lived 5 hours away. I took a drive one weekend with the intent of staying at her mom’s boyfriend’s place, because she lived with her mom and she wasn’t comfortable with me sleeping there. Totally fine.
I get there and chat up her mom and her mom’s boyfriend a bit before we head out on the date. The date goes great, we go to her place and make out a bit, but her mom calls from the boyfriend’s place and wants me to head over there. Ok that’s fine, I say goodnight and head over. It’s like 5 minutes away and it’s an apartment building that I need to get let into. I call and call and no one answers. I’ve slept in worse places, so I just fall asleep in my car.
I get woken up to the mom’s boyfriend knocking on my window. He then just hops into my car and I quickly find out that he’s high as a kite. He starts telling me about how he views my new relationship like a beautiful ball of light and that he thinks that it’s going to go really well. I awkwardly say thanks and try to say that I’ll just sleep here, and he insists that I come up. He proceeds to invite me to have a threesome with the mom and him and tells me that I’ve “got to be packing more heat” than he is. Uh, thanks guy but no. He still insists that I sleep upstairs on the air mattress and I say fine.
I go upstairs, get the air mattress set up, and lay down. He says good night and does one of those fake trips and falls on top of me. I push him off of me and help him up and into his bedroom. He tells me to make sure that I say goodbye in the morning before I leave. I do not sleep at all. I text the girl and ask her to text me as soon as she’s up so that I can leave. I shower and get ready super early and just stare at my phone waiting for a text. When I finally get it I go to say goodbye and walk in on mom and boyfriend in the act. I just shake my head and walk out. At least the girl was awesome.
#41 Red Flags
So I met this girl on Tinder. She seemed nice enough at the time and I was sorta new to this whole Tinder thing so I must admit the red flags slipped right past me. She rocked up half tipsy in a torn dress. Now I’m not one to judge people’s lifestyles and I was starving, so for some reason I decided to press on with the date. Bad decision.
I spent the next three hours listening to her moan about her current boyfriend and how he was such a controlling guy because he wouldn’t let her go out on one-on-one “catch ups” with guys at bars. When I finally came to my senses and told her that I didn’t particularly want to be on a date with a girl who was seeing someone, she threw her drink at me and accused me of assaulting her. Thankfully, the bartender had been watching the entire series of events and took my side on it. She got thrown out, and I didn’t go on another Tinder date for the next few months.
#42 Cowboys and Hallucinations
A girl in college had tickets to a rodeo and asked if I wanted to go. I don’t like those kinds of things, so I got super, super high beforehand. I hated it. It just seemed like rednecks messing with animals the whole time. Then one of the horses jumped up and fell on its neck and just laid there lifeless. I started freaking the heck out because I was pretty sure I just watched a horse die. They had to drag it out of the arena on a fence pulled by a tractor. She insisted that the horse would be okay, but I left and never talked to her again. In short, I got too high and possibly watched a horse die.
#43 One for Two Dining
I served this couple, and the dude would not stop eating her freaking food. Other table actually noticed, and we casually “people watched” the date together. Girl looked miserable. We asked if she wanted the rest of her food boxed up. She said no, but the guy was like actually, yes. It was painful.
#44 You Could Be My Other Guy
I’m a dude. I was about 16 at the time. My female cousin tried to hook me up with her “nice friend” whom I had shown interest in after meeting her at a family gathering. We text and talk on the phone for a couple weeks. Later we agreed to meet at the mall. We get to the mall and the girl shows up with another guy, who is her boyfriend. Yes, she introduces him as such and all that.
Apparently, he was her ride to the mall. My cousin didn’t think this was odd. I was highly annoyed the whole time because the girl is really fine. We walk around the mall, the girl, my cousin, and myself. The boyfriend waits in the car. The girl tries to get me to buy her stuff in the mall, I lie and say, “Oh, I don’t have it like that right now.” She tries to hold my hand, asks me to get her something at the food court, the latter I give in and do.
I tell my cousin I’m ready to leave. And the girl goes, “You’re cute. And sweet. You should totally be my guy.” I was dumbfounded, “Don’t you already have a bf?” “I could have two! Besides, he’s just my brother. I don’t have to commit to him.” My jaw drops, and I just tell her no thank you, and leave quickly. My cousin asks what’s wrong, STILL no seeing the problem with her friend’s relationship status. I’m still weirded out by that to this day.
#45 No Necking for This Therapist
So, I’ve read a lot about neckbeards. I’ve never seen an actual neckbeard in person, however. Then I went on a Bumble date with this physical therapist.
The beard growing out of his neck, alone, ended any desire that I had. I get it now, everyone.
#46 Red Alert!
I met up with a guy I met online. I picked him up from his place. Anyways, we’re both Asian (this is significant). Seemed like a normal guy at first. Talked about ourselves, our hobbies and things. At one point, I mentioned I was pretty “traditional” in reference to how my family still marked the calendars for certain days to burn incense and pray in front of the family shrine.
I guess he took that to mean something else. He said that was great, and then launched into this…crazy racist rant about Asian females who date white guys. This guy was like a full on a racist Asian. Like the Asian equivalent of a Nazi. Was obsessed with the idea of purity and not dating outside of our “race.” Was incredibly relieved I’d never dated a non-Asian before (it wasn’t even a conscious decision, it just never worked out that way). Started talking about how Asian females who slept with white men were race traitors.
Sometimes he would contradict himself by saying things like at least girls who date white guys will give birth to half-Asian, half-white kids and they weren’t really Asian, and how it would remove those women’s inferior genes from the Asian gene pool. And he just went on and on and on and would not shut up. I was just sitting there awkwardly nodding along because I had absolutely no idea how to react to him because What. The Heck.
Every once in a while, he’d interrupt himself and reassure himself that I wasn’t like those other “females.” In the end, I was too nice and too much of a pushover to just walk out and leave his sorry racist butt there. I sat quietly through his rant. Made polite conversation afterward like normal and drove him back to his place. I ignored all his texts afterward. In hindsight, I regret I didn’t just publicly call him out and abandon his stupid butt there.
#47 Turning To The Feet
Was set up on a blind date by a coworker. Things went reasonably well—ok conversation, he seemed to be genuinely nice. My co-worker and her boyfriend double dated with us for moral support. We went back to the co-worker’s house after dinner to watch a movie together. That’s when things got weird. Co-worker and boyfriend left the room to give us some “alone time.” Immediately, my date tried to kiss me.
It was one of those approaches with his tongue hanging out. I nicely rejected the kiss, saying it was too soon for that type of affection for me. So he shifted his attention to my feet. I was wearing open-toed shoes and he grabbed a foot in his hand and asked if he could rub my feet. I declined and he began to beg. Told me that he loved feet and would love to suck on my toes. I declined again, started to get a bit scared. He made a last ditch effort by asking if he could just sniff them once. I gathered my things and left ASAP.
He followed me to my car and tried to beg me in a baby-talk voice to come back, me and my “widdle piggies” (toes). I kept expecting a camera crew to pop out from behind a tree proclaiming that I had indeed been “punk’d.” I was as nice as possible about everything, citing that I just needed some time to get comfortable with someone before becoming affectionate. I pulled out of the driveway in such a hurry that I squealed my tires a bit.
I had no intention of seeing him again since he had violated my personal space so much. I (probably wrongly) passive-aggressively ignored his phone calls and myspace messages. He couldn’t take a hint though, and called 20 times in one day. I finally manned up and told him that I wasn’t interested in pursuing a relationship. He immediately got nasty, called me a cock tease, and told me never to contact him again. Weirdest date ever.
#48 The Bad Move Was Listening to Mother
In the 90s I managed a busy furniture store with lots of customers. As an attractive girl in her mid-20s (and not wearing a wedding ring, as I wasn’t married) I definitely got hit on. Frequently. We sold a lot of mattresses so that alone lent itself to many awkward exchanges for me. One day I had a customer, a lovely lady in her 50s who I spent a lot of time with in the store.
As we were finalizing her invoice, she went on and on about her son who had just moved into town (from near where grew I up) and how I really needed to meet him. She explained how attractive he was (she also told me about his schooling and job, but really pushed his physical attractiveness) and after much badgering I agreed to meet him on a very blind date.
We talked on the phone (probably on landlines, this was pre-cell-phone era!) and met at the pub. He was one of the most physically unattractive men I’ve ever met. What she described and what I met were not in the same universe let alone ballpark, at least to me. So, I talked with him for a bit but unfortunately talking to him was like wrestling wet cardboard.
I’m a sucker for a sarcastic, witty guy and no matter how he looked, if he had been a bit cocky and had a sharp sense of humor, he could have won me over. But no. So, I tried for a few hours to make some conversation and realized it wasn’t happening and so I found an exit point and used it. I didn’t just bolt on him, I did give an excuse to leave, but at that point, I learned that MOTHERS WILL ALWAYS THINK THEIR SONS ARE GODS no matter what the kid looks or acts like. That was the first and last time I was ever “set up” by a relative stranger.
#49 Love Bites
I work in an Italian restaurant. A few years ago, I waited on a guy and girl who met for the first time upon arriving at the restaurant. There were awkward pleasantries exchanged at the door and then they were seated. When I was taking their order, the guy asked if we had soup because he had mouth surgery a few days prior and chewing food was still a little rough.
We don’t have soup, so I explained that the “softest” food on the menu was gnocchi. He ordered the house gnocchi and proceeded to cut each tiny dumpling into four or more pieces and slowly chew each piece. He ate that entire dish over a three-hour period and the girl stuck it out for the whole thing. She looked miserable and I’m pretty sure they never saw each other again.
#50 Wrong Waze
I met a girl from Match. All went well, but as a veteran online dater, I only met her for a drink so that we’re not stuck in some awkward dinner thing if we hated each other; apparently that was set for date #2. So, on the second date, she asked me to pick her up outside her place, which I did. I ended up selecting the wrong place from Waze, and we went way out of the way. I could sense she was a little annoyed, but I corrected it, and off we went to the other location.
Dinner with plans to go see a band after. We had an hour wait for a table, but luckily that hour was filled by complete utter silence. Dinner was awkward. Not wanting to be rude, I asked her if she still wanted to see the band. Nope. Take me home. Oh thank god. So we pull up outside her apartment building and she looks over and says goodnight.
She grabs the door handle but it doesn’t open. It sticks and you have to lift and pull the door in before it’ll open. Her eyes are WIDE OPEN looking at me, as she tries to open the door frantically. I tell her it sticks, and lean over to open it for her. She SCREAMS. I mean, like I’m going to hurt her or something. I get the door open as she counters my ear with her screams. She hustles off up the walkway to her apartment and didn’t even close the door to my truck behind her. No third date.
#51 Biting the Nail
I bit straight into a bite of food, forgetting how hard it was, and almost cracked my molar.
#52 Love and Politics
We somehow got on the topic of politics. She pulled out a mini copy of the constitution that she kept in her purse and tried to convince me on her viewpoints. Don’t care. Still got it on. She was also married.
#53 Seeing Siblings
I was on a date with some girl in high school and I ran into her sister (I dated her like a year before) with her current boyfriend—my brother. Awkwaaaaard.
#54 The Goods Are Never as Good as the Gossip
It was ninth grade, my freshman year of high school. There was a guy that everyone was repeatedly telling me apparently liked me. He had asked if I was going to the school football game a week prior, but I had just chalked it up to friendliness and answered him with an honest no. Eventually, I got annoyed of hearing it from everyone else.
I confronted him with a blunt, “Dude, do you like me or not?” Upon his confirmation, I asked why the hell he hadn’t just told me earlier. “I invited you to go with me to the football game, but you said no!” I came back with: “No, you asked if I was going to the game!” From that interaction, we decided to go out on a first date.
We went to McDonald’s. Where I paid for everything and the dessert that he wanted. We then went back to school. I tried to kiss him and he freaked out slightly, I’m talking hyperventilating and muttering to himself. We dated for a few more months before I kissed him a little too passionately one day, and upon his freak out, re-considered dating him. We broke up the next day.
#55 Playboy Pays Well
I definitely have seen a lot of awkward last dates. I used to work at a very small neighborhood restaurant. Everyone who came in was a regular. Most were couples in their 40s-50s out for a quiet dinner, but there was one stand-out. A VERY handsome man in his early 30s would come in, it seems, only to break up with women. About twice a month, he would come in with a beautiful woman, and partway through their meal she would be crying. I always tried to clean the tables near them for as long as possible, but I never heard much of his speech. He always tipped well and was super nice to me and my coworkers, it was just brutal seeing him bring in a new lady and knowing what she was about to go through.
#56 A Portrait of the Artist as a Young Woman
I took this artsy fartsy girl to a theater for a play. Cool, whatever. Afterwards, we’re walking back to my car and everything is going normal. Small talk and all. She suddenly breaks down into tears and cries about missing her ex. Darn. I guess we’re not getting Chinese food anymore. I take her home. She lives in boonie-ville. Foggy as heck at night. I drop her off at home, thinking I’m never taking her on a date again. Head back home. Phone loses signal because boonie-ville. I run a red light because of the thick fog and the GPS starts going nuts. I hit another car and total my car. 0/10, would not go out again with an artsy girl who was secretly still stuck on her ex at the cost of an entire car.
Went to Montreal for Ile soniq (an EDM festival similar to Tomorrowland). Met a girl on Tinder while there and decided to meet up at the festival. We meet up at the metro station on the way there. She seems normal enough, she looks like her pictures which is good, everything seems A-OK. We get to the festival grounds.
While we are getting our bracelets, she asks me, “So what kind of music is this?” She had never listened to EDM before. I figure whatever, she’s adventurous, seems outgoing enough, she’ll probably enjoy herself either way. There were 3 stages, all with different kinds of EDM. The first stage we go to is very bassy and not her thing, so we go to a different one and she actually likes it! I’m relieved.
Two hours later, she wants to leave. I tell her we paid $150 a ticket and I’d like to stay. Cue the rest of the day her complaining about everything from the food to the music to the other people there. She made a huge scene and yelled at a guy because he accidentally bumped into her in the middle of the crowd. Lots of people stopped and watched. I was mortified. Around 9 pm I finally relent and decide to leave with her back to my hotel room. Queue the worst intimacy of my life. I missed Excision and Porter Robinson for that. Still regret not just ditching her.
#58 Tapped the Glass Too Soon
When I was waitressing in college, I witnessed the single most embarrassing thing to happen to a person to date. Right in the middle of their dinner (and in the middle of our Friday night dinner rush), this poor guy stands up, taps his wine glass to get everyone’s attention, and then proceeds to tell EVERYONE what a fantastic person his girlfriend is, how much he loves her, and how lucky he is to have her in his life.
The whole time this is happening, she is just sitting there watching him with the most boring look on her face. It was so weird. Kind of like, “Yeah, tell me something I don’t know.” Then the poor guy pulls out a ring, gets on one knee, and asks her to marry him. She gives him the most disgusted look imaginable and says, “THIS is the ring you expect me to say yes to? Are you stupid? Could you be any cheaper?” Then she gets up and walks out, leaving the poor guy just kneeling there. I didn’t charge him for the meal.
#59 A True Gentleman Wastes No Meat
We went for burritos. I’d never eaten burritos before, and what I didn’t realize was that there’s definitely a wrong way to do it. There’s planning involved. Toward the end of the burrito, I felt something slip in the structure of my meal. It became clear that the burrito was going to slither into an unwrapped state imminently, the tinfoil it was wrapped in wasn’t going to stop it, and I had a choice.
I could either watch my tasty treat of cheesy beef flop onto the floor, or I could eat it, all of it, right now. I didn’t regret my decision; but I did have enough of a vague sense of dignity to vocalize a muffled “fffwrrry” to my date as I fished tinfoil out of my packed and leaking gob, and used the other hand to wipe a stray fleck of beef that was oozing down my beard.
To compound the awkwardness, it must have been a full minute and a half of silent heavy breathing through my nose before I could clear my mouth enough to more thoroughly apologize and explain. I don’t know if she agreed with my choice; but I think she respected it. The thing is, there was actually a second date, and a third, and I think a fourth. No matter how disappointing you are, sometimes a lady will be in a dry spell longer than your own. Or possibly have a fetish about fat scruffy men suddenly and inexplicably fisting an entire burrito into their already-stuffed and dripping maw, I never quite ruled that one out.
#60 You Can’t Charge That to Overtime
I worked at a Subway a long time ago. My regular doctor came in with one of the medical assistants (not his wife). They were sitting side by side and she kept rubbing his leg. Dude, you’re a doctor. Use that brain of yours. If you are going to be a jerk and cheat on your wife, at least go on dates in another town where people won’t recognize you.
#61 What Type Of Stage Name Is “Brad”?
I met this guy originally at a cocktail bar. We went to dinner on the first date, and then for the second date we went to a Comedy club. The first problem was he kept nudging me when I laughed, like I was embarrassing him. Of course, I was irritated by this, but tried to tone it down since I still had two more hours to sit through.
Halfway through, he’s just acting real nervous and then the MC gets up on stage and says “Welcome Brad to the stage”… The guy I am on a date with is not named Brad. Brad is his stage name. He goes up on stage and proceeds to make two incredibly racist jokes. Tables turned. I was embarrassed and nervous for the rest of the show. Joke was on me. We didn’t go out again.
#62 My Heart & Liver Are Full
My worst date ever was also completely my fault. Witness, me. Planned on going to a bar with a pretty wild reputation (her idea), friends warn me to not drink much. 1 drink max. Their stuff is strong. We get there, and I have the one drink and, much like my friends had said, I felt pretty good. So when she wanted to split another, I said I was down. I do not eat anything at said bar except for an edible. Still not feeling like I’m out of sorts so when she says, “Let’s go back to mine,” I’m down.
As we walk there, I am getting more and more intoxicated, but it isn’t until I’m sitting on her couch that I start thinking, “This is bad.” I go to the bathroom once and puke. And then more or less take a nap on the cool, cool ground. She’s knocking on the door asking if I’m okay and I’m acting like all is well. Finally, I come out and this woman has made me food so that I can sober up.
I am too nauseous to attempt eating and the smell kinda makes me feel like I have to puke. So I go back to her bathroom and take another nap. Next time she knocked on the door was to say it was late and she should get some sleep. I walked home. Friends mocked me nonstop for doing the exact opposite of their advice. Immediately after I felt like ritual suicide would be the only way to avoid my shame. I got a second date though, so I guess I’m charming enough.
#63 It’s A Small World
Second date. Meet a girl at a nice dimly romantic bar that she picks. We talk for an hour, everything is great. Suddenly she starts crying saying that she can’t take it, she’s hung up on some guy. She proceeds to attempt to dump all this crap on me about some guy she’s been seeing but they took a break from each other and she thinks he’s been hanging out with this other girl.
I ask the guys name and almost crapped my pants because one of my friends had actually been dating him. I mention this to my date and she just loses her mind even more. Crying, getting pissed, and all the while I’m in shock. I got up like five times lying that I had to piss just so I could go to the bathroom and be like WTF. Finally, I come back to the table and just say I gotta go. She calms down and apologizes and I bailed out. We stopped talking soon after.
#64 Everything Stays In the Family
I ended up going back to his house where he lived with his father. In the middle of the night, I farted so loud I woke up him, myself, and his dad. Because you can’t be blamed for anything you do whilst sleeping, I just stayed as still as possible. When we emerged from the bedroom in the morning, running into his dad, he said, “Son, you woke me up with that one last night!” Chuckling away. “Yeah sorry, dad, must have been all the beer,” replied my date, winking at me. We’ve been together for three years now and are due to be married.
#65 You Can’t Bank on Love
Mid-20s-aged couple on a date. First date I think but I’m not sure. It seems a bit awkward but they make small talk throughout dinner. When it’s time to pay, the guy asks for separate checks. Girl looks surprised. He pulls out his card, pays, and then goes to the washroom. I run the girl’s card (she already looks nervous) and it gets declined. We try again, it is declined again.
I ask her if she needs a moment to figure it out (check her online banking or whatever) and she says yes. Guy comes back. She runs her card again (declined) and he sits stone-faced while she is getting more and more anxious. I walk away again, and when I come back the guy ends up paying for it. He wasn’t thrilled. It was super awkward for all of us, but I cringed so hard when it was obvious that she had just EXPECTED him to pay for her.
#66 Cul-de-sac Fun
Got set up on a date with this pretty awkward guy, he picked me up in his car which was sort of cool considering we were in high school but oh my god he was a nervous driver. So nervous in fact that he accidentally ran a red light, lost his mind and ducked into a residential area to sit at the end of a cul-de-sac freaking out thinking the cops were coming. I tried to explain that if a cop had seen him we’d have already been pulled over but dude was too freaked out. I don’t even remember anything else about the date, just that. It was uneventful and I never really talked to him again because we had nothing in common.
#67 My Mistake
I was on a first date with a girl I also worked with. We’d been flirting for weeks and had wonderful chemistry. Our date was great and had a life of its own. She drove. At the end of the 6-hour long date, we were sitting in her parked car in front of my house, continuing the captivating conversation. We had a work meeting the next morning, so when it came time for me to go, I started to exit the car and said: “See you tomorrow.” She sheepishly said, “I can’t wait that long.” Without thinking, I replied, “Well, you’re gonna have to,” and slammed the car door. I didn’t realize what she meant, or how what I said came across, for some time, like the next day.
#68 No Comparison
The first date was on Valentine’s. We had been friends before, so I did the right thing and got a card. Two drinks in and she explained in intimate details, for around 30 minutes, how big her ex was and how he would pleasure her for “hours on end.” Needless to say, I wasn’t exactly at top form after that treat. Still, ended up getting a nugget share box so it wasn’t all bad.
#69 Hospital Waiting
I had a dud first date—we had nothing to talk about, and none of the social skills or inclination to make small talk. We made it halfway through the second drink before both abandoning the idea. I walk her back to her car—she collapses on the way. I call an ambulance and end up in the emergency waiting room wondering exactly what my obligations are to a girl I don’t know. I stick it out for four hours until she’s discharged. I ask her to call me when she gets home, to make sure she gets there ok—she doesn’t call.
#70 When Ghosting Was the Kinder Option
Immediately after the date, I spent 20 minutes complaining via WhatsApp about how bad the date was. I thought I was talking to my friend with the same name as my date. It was my date and not my friend. I felt bad about it for weeks.
#71 This Relationship Won’t Hold Water
This woman arrived before her date and was sitting alone in the booth waiting. She had a kind of generally angry air about her. This woman was enormous, and the hostess had seated her at one of our smallest booths. Her stomach was fighting the edge of the table. She ordered a glass of wine and sat there drinking it. By the time the guy arrived, she had finished it. I asked her if she’d like another glass, and she said with a scowl on her face, “I don’t know. It depends on whether or not he’s paying.” The guy looked kind of embarrassed and said sheepishly, “Uh, yeah I’m paying…” I wanted to tell him to run far away.
#72 Making The Date Age Appropriate
I went on a date with a boy when I was about 16. I lied about my age and even though I literally looked 11, he still believed me (super dumb of me, right?) He was in his 20s. “Let’s get a drink, yeah?” Me being too weird to tell the truth, I agreed. Flash forward and we’re outside of the bar, it’s our time to go inside and the bouncer checking ID asks me about mine. “Uhhh, sorry, I must have left it at home.” I defensively exclaimed. He knew I was bullshitting. I did too. My date looks at me weird and he starts interrogating me, I literally cracked with embarrassment.
I started sobbing and at that point, I tried to run inside the bar like I actually had a chance. I even threw a tantrum causing a HUGE scene. Way to show my true age. After, he looks at me with a blank expression and I honestly was crushed. We’re in the car leaving at this point and it was nothing but silence until he was like, “let’s go somewhere age appropriate then.” “Age appropriate?” I was shocked, he wasn’t even mad at me. I didn’t know what to do with myself, I just sat in the back of the car, mentally beaten. We drive for a while and I honestly thought I was going to get kidnapped. Then eventually, we pull up to a Chuck E. Cheese and he leaves me there.
#73 Two’s Company, Four’s a Crowd
I asked a girl on a date. She said sure. We agreed on the details, I’ll pick her up at 4 pm, then we can do go-karts at the local speedway. Unbeknownst to me, she invited 2 of her friends. Since I was a spineless 19-year-old at the time, I couldn’t assert myself to tell her friend not to smoke in my car, and also that I don’t want to pay for their go-karting. Ended up paying around $300 for all 4 of us to go race, but my “date” had to stop at the 3rd lap because she crashed with some stranger.
#74 The Naked Man
I’ve had a lot of terrible dates, including someone picking me up with their mother and having her attend the date, but the worst by far was when I was 19. I went to this guy’s house who had alluded to the fact that he lived alone. We were gonna go swimming then go out for lunch. I show up and it becomes apparent it’s his parents’ house and they were currently not home…Ok kinda weird but no big deal.
We’re having a beer getting to know one another when out of the blue, he INSISTS that he show me something in his room. I say something along the lines of nice try, but I’m not gonna go into your room so you can try to put the moves on me. He continues to insist that it’s actually really cool and I HAVE to see it. I’m visibly annoyed but follow him anyway.
We get in there and within three seconds flat this guy gets completely naked while I’m just standing there dumbfounded. To this day, I have never seen someone undress so quickly. He’s standing there like this is his grand reveal, expecting me to just throw myself on him or something. I tell him I remembered I forgot to do something and need to go home and basically run back down the stairs while he’s chasing me, trying to get dressed and follow me outside. I book it to my car and leave very fast. Dude then proceeds to call me every few weeks for 1.5 years, leaving me creepy voicemails how he hopes I’m not hanging out with other guys and how he misses me. Worst date ever!!
#75 The Weight of the Dating World
Realizing that I was the guy who’d gained too much weight since his profile pic was taken. At least her look of disappointment motivated me to lose 40 lbs.
#76 Making A Mess On The Ice
I met a good looking girl and after talking for a bit, she told me that she liked ice skating. So, I took her ice skating and had a little dessert prepared for when we were done. She was awful. She wore a skirt and a revealing shirt, with a very light jacket. Therefore, she was cold the entire time. What didn’t help that problem was that she kept face planting into the ice and getting covered by ice. After multiple falls and her beginning to bleed, I suggested we get off the ice and have some dessert. I grabbed the bag full of stuff and made our way toward the exit.
Right at the exit, she managed to fall again and, in my attempt to grab her and keep her up, she knocked the bag out of my hand, and then fell on it. She was then covered in ice, wine, and chocolate. It was not a good date. Needless to say, I didn’t get laid. It was an amazing amalgam of ice, blood, wine, and chocolate.
#77 Not All Vegetables Are Good For You
I went on a blind date when I was 16 to dinner and a movie. We went to go see I Still Know What You Did Last Summer. I got peer-pressured into taking mushrooms for the first time (I’d never done ANY illicit substances before). I ate them with a few friends that tagged along for dinner. We went to the movies after dinner, just us me and the girl.
Well, at the beginning of the movie Jennifer Love Hewitt wakes up from a nightmare screaming, I proceeded to scream and run out of the theater. The rest of the night for me finished in this order: called dad from the payphone and told him I was tripping balls (as a 60s dad, he understood). I stayed in fetal position out front of the theater.
The girl’s dad picks her up with her crying and he kicks me angrily asking what my problem was. Dad picks me up. Dad drives me home while on the way looking at me and moving his mouth without saying anything just to mess with me. Dad tells me to go to my room and don’t talk to my mom. I have a conversation with my cat and black out.
#78 No Room for Improvement
Had a couple come into my restaurant. Guy is telling woman about some real estate investment opportunities he has coming up (for himself). She tries to tell him she doesn’t think it’s a good idea, and he responds with, “No one asked for your opinion, you don’t know what you’re talking about.” She sat in silence for the rest of their meal, looking at her phone. When he goes up to pay, and I go clear some of their dishes away, she tells me it’s only their second date, and she doesn’t think she’s going to see him again. Couldn’t bring myself to respond with anything other than, “Please don’t.”
#79 The Past Comes Back Slowly Sometimes
I was on a train coming home from work and saw this GORGEOUS girl. Couldn’t keep my eye off her. Then I realized I used to go to church with her like 15 years before! We weren’t friends… it was early puberty for me so I was still in the picking on girls and being mean to them phase, but oh well, that’s in the past!
I went up, asked her how she’s been what’s she’s been up to. Ah reconnecting! I asked her where she worked, and she told me, turned out we were about a block apart in the city, so I asked her if she wanted to grab lunch one day. The next day, I text her, we grab lunch, and it’s going splendid, but something is off….. She is asking very general, “first date” questions. Now, while I’m more than happy to answer, it was bothering me…. then it hit me. She didn’t remember me.
I must have been so friendly, confident, or something when I approached her on the train that she agreed to the date. And now here I am, thinking I’m reconnecting with someone, and she didn’t remember me… Well the date went great anyway, she had off the next day so we decided to meet up the day after… Fast forward to the next night and I get a text from her. “I just remembered who you are. Don’t text me again. Don’t come near me on the train.” Apparently, 12-year-old me was a real jerk.
I was making out with a girl on a cold evening on her unlit front porch. I just thought my runny nose was from the cold. But when we turned on the lights I realized I had a bloody nose. Her face was COVERED IN BLOOD. There was no second date.
#81 Surprise! Dating A Coworker Goes Bad
Last year, I started screwing around with a coworker of mine. BAD IDEA. We decided to go to a party as our first date-like thing. The party was at her house (she had like six roommates in this giant house). Now, I’m not really a big drinker, but these people (all of whom are well into their 20s) were just getting schwasted off of Barton’s Vodka. I’ve never seen a more childish abuse of alcohol.
Yada yada yada, everybody at this party (25 people or so?) started drinking at about ten, and were all passed out in piles of their own vomit all around the house, high-school style. The girl I’m with, after throwing up on her bed, begs me to stay and take care of her. Because of my hatred of immature tipsy people, I simply leave (kind of a jerk move, I know). The next day my boss talked to me and said that I wouldn’t be working with her anymore because she threatened to fill out a harassment case or something against me. Whoa! Worst date ever.
#82 Daddy Big War Games
I went out with a girl in high school and did the usual, movie and dinner. It had been going great up until dinner when she stumbled over a curb. I went to catch her, and promptly whacked her in the face with my head. This actually broke her nose, which lead to me panicking and trying to fix it. Of course, that was a bad idea, and I think I made her nose bleed more to be honest.
Thankfully, she wasn’t upset at me (I spent a good half hour freaking out over it), but there was a veeeeeeeeeery awkward and at one-point terrifying conversation with her dad when I brought her home. He was a former marine who served in Vietnam and did the usual “scare the bejesus out of the daughter’s date” by coming out sharpening his Ka-Bar knife when I picked her up—needless to say he really didn’t like or trust me after that. The girl and I dated for a year and we’re actually still pretty good friends. So, I guess it worked out okay in the end.
#83 Overtime Means Double-Time…
I used to work the bar at a restaurant that was walking distance from a very rich neighborhood. One of my regulars was an NFL player who would bring his fiancé in a couple times a month. One day, the fiancé came in alone and already very tipsy. She sat on her usual barstool and started rapid-fire typing on her phone without ordering anything.
I kept my mouth shut because she was already wasted, and she usually tipped me very well. I turned my back to type in someone else’s order, and I heard someone yell and then the sound of breaking glass. Turns out Mr. NFL player had walked into the restaurant with another woman. The fiancé had picked up someone else’s drink and threw it at his head.
#84 Must Love Pigs
Met a girl online, talked it up, and while she seemed a bit immature, thought heck, why not? She casually mentioned she really liked pigs. What she meant to say was she was obsessed with pigs. OBSESSED. Go to one of the best restaurants in the area for a first date (bad idea). Sometimes pictures are from someone ten years prior, or the person hides things, etc. But that wasn’t the problem. She looked just like her pictures. But I didn’t even have to have seen her first, because everything else gave it away.
She came in a giant T-shirt that had a sparkly pink pig on it. Earrings? Pig earrings. Bracelets? Yep, pig bracelets—I swear her dad might have been Homer Simpson. She had this headband on with a little pig on it. Her shoes? Yep, pigs on the front of the toes! But best of all? She had a GIANT (or at least it seemed giant) pink purse with the face of a pig on it.
You could not stop seeing it once you did. And I’m sure everyone else in this nicer/classier restaurant saw it too. I felt overdressed with her but under-dressed with every other couple there. It was beyond embarrassing. For some reason which I have to convince myself was politeness not stupidity, we still had dinner. But Reddit, it was the fastest damn dinner I’ve ever had at a sitdown place.
I practically blurted out something about how “oh, you really do like pigs…” which she started giggling (oinking?) and going on about how everything she has is pig themed. Then she wouldn’t stop, and it became the dominant part of the conversation. There were a dozen other things that made it a train-wreck, but these were the clinchers to a solid 0/5 date. I remember afterward consoling with a friend of a friend, because I had to tell someone; and then I promptly buried this as my worst date.
#85 Doing Due Diligence
I met somebody through Plenty of Fish and went out with her for coffee. Once we sat down, the first thing she asked me was how much money I made. I didn’t discuss figures, but I said that I was doing alright. She then regaled me with stories about her overdue bills, and how she just didn’t pay them because she didn’t have the money, and how her last credit card only had a $5,000 limit, and how quickly that gets used up. She just didn’t seem to have a grasp on how money, interest, and credit ratings work. And by her own admission, she had debts of tens of thousands of dollars.
She made it quite clear that she wanted somebody who would take care of her financially, and if things worked out, co-signing on a credit card for her might be in the future. The whole date felt like a sales pitch and made me feel like a wallet on legs. I declined going back to her place afterward, and instead went home and had a shower to wash the stench of loser off of me. And that was the last date I had before the one where I met the woman who became my wife.
#86 G.I. Jane And Neediness
He wanted to watch a movie at his house. Turns out, he wanted to watch G.I. Jane. Turns out, it’s his favorite movie. Turns out, he gets so pumped when watching it he wears his army fatigues and spontaneously does pushups every five minutes. Then we go for a walk and he insists on holding my hand and practically hanging on it for the entire walk.
Finally, I get to my house and send him home, relieved to finally be alone. Five minutes later, I hear something hit my window. Then again. He’s outside, throwing rocks at my window. He tells me he loves me, and gazes up at me with a grin. He had to see me again! I tell him, “Go home!” I think about how I’m going to break up with this extraordinarily needy dude. It digs at me all night. In the morning when I leave for work I find flowers under my windshield wiper, and a poem. First dates can be gruesome.
#87 She Didn’t Appreciate My Love Games
I totally ignored her and played my Tamagotchi the whole time. I was in middle school. She had a friend break up with me at a party a week later if I remember correctly. I deserved it but being dumped did not trouble me as much as I thought it would. Cause, you know, I still had my Tamagotchi.
#88 Too Young to Talk?
Saw a really young couple, likely 13 or 14, come into my diner and not say anything to each other. Neither could look each other in the eye, they were so shy. They ordered their food barely above a whisper. Occasional cringe faces were made at the food they were staring at. They were having a very awkward time and it was painful for them as well as me.
#89 Going On A Date With Your Buddy
A friend set up a double date with a girl he was dating sophomore year of college, and she said she’d bring her friend, who she explicitly said was a female friend. My buddy and I met her and her friend at a bowling alley for rock and bowl. She had brought her cousin. Her male cousin. Who was 15. Then she basically just spent the whole time talking to her cousin and ignoring my friend. So, me and my friend just had a heck of a fun time bowling and chatting it up with the other people at the alley.
Then we all went to get late night appetizers from Applebee’s and she ignored my friend the whole time as well, so we made it our goal to make the waitress/waiters around us laugh as much as possible. My friend and I headed back to his mom’s so I could get my car and told his mom what happened and she was like “So… you two basically went on a date with each other.”
#90 First Is the Worst
My worst first date was also my first date ever. I was about 14 or 15. The girl I liked asked me if I wanted to go on a date, I was over the moon. She told me to meet her at the park. When I got there, she was there with her friends and they all laughed at me for thinking she would ever want to date a loser like me.
#91 Bringing Race Into The Date
Two and a half years ago, I went to a concert at the Fillmore in San Francisco on a first date with this curvy blonde. We got dinner at a little Italian place, then we took a walk around Japantown while we were waiting for the doors to open. She starts spewing a wave of anti-Asian racism, including her desire to “end off all the Chinese boys.” My best friend since fourth grade is Chinese. After the concert, I stuck a twenty in her hand and told her it was cab and BART fare, so she could find her own way home.
#92 Anointed in Regrets
I had just read in the Bible how they anointed themselves with oil. So I tried washing my hair with a half cup of olive oil before the date. Turns out it doesn’t wash out. We went to the theatre. I had oil puddling in my ears the entire date. My socks kept getting oily. I smelled like a pizza. I didn’t get a second date. College at BYU was weird for me.
#93 Cupid Goes to Daycare
I was serving a couple probably in their mid-20s. It was Valentine’s Day and they were arguing a lot (probably because it was a chicken wing place and Valentine’s Day). The guy ended up calling me over to the table to calmly ask me, in front of his date, “Do you have a high chair or a booster seat since someone wants to act like a darn child?” I was speechless, she wasn’t. They left soon after that.
#94 Parents and Video Games
I met a guy from OKCupid. The first time we met up in a public place and just had a casual chat. It wasn’t a horrible date, but it wasn’t very memorable either. I decided to give him another try because it could have just been nerves. The second date he invited me over to his place… I knew he lived with his parents, but I kind of assumed they’d be away. They weren’t away. They kept coming into the lounge room and giving us iced tea and chips whilst he played XBox in his track pants (no shirt) and I sat there awkwardly watching. He didn’t really speak much to me. It was 11 pm, and he was in his 30s.
#95 Wet Date
First time out with my now fiancé, we were at a local sushi joint. I was telling a story (actively using my hands) and knocked a glass over and we both watched it slowly roll off the table and onto the floor. Then not even five minutes later, a little probably two-year-old girl is running around her family’s table as kids do, stops right next to our table, and vomits everywhere.
#96 Take a Hike!
I took a girl hiking, and to cut to the point, we took longer than expected. She was apparently afraid of the dark and was running around and telling me that we were going to die. Not the best experience. I basically had to push her along the trail, taking about an hour or two before we finally got back to my car, where she promptly thanked me for “such a good time.” Yeah.
#97 What Is That Smell?
Wasn’t my date, but I had gone home with a guy I had been seeing and when we got there his roommate was curled in a ball on the couch looking pretty shaken. We asked him what was wrong and it took him awhile to get it out, but he finally told us what happened: He took a girl home from the bar and they started tearing each other’s clothes off as soon as they got through his bedroom door. She said she was self-conscious though so she wanted the lights off. He switched them off and they started fooling around. She starts going down on him when all of a sudden, the guy notices this horrible smell.
He mentions it but she tells him to just ignore it, he’s probably imagining things. Finally, the smell is too much so he switches the lights on. That’s when he sees it. Crap. Literal poop all over her and all over the bed. He is completely dumbfounded, doesn’t know what to say or do so apparently all he yelled was “POOP!!!!” She grabbed all her clothes and ran out of the apartment crying without saying a word and, presumably, still covered in poop.
He threw his bedding out, took an hour-long shower, and refused to go back into his room. Pretty much ended our night too. To this day I still wonder what on earth happened—was she into it and was hoping he would be too? Was it an accident and she decided to just go with it? I don’t know which scenario is more horrifying, to be honest.
#98 No Clowning Around
I met this girl on Tinder. She seemed cute enough and the conversation wasn’t as stale as the other matches I had, so we decided to meet up over coffee. Queue the day of, I go to pick her up at her house. I knock on the door and she opens. She was, to say the least… not at all like her pictures. She was much bigger, and her face didn’t even look the same. I’m already disappointed but I’m already here and it would be rude to back out now. So she gets in my car and we start driving to Starbucks. On the way there, we talked in the car for a bit and it becomes apparent to me that she is an “XD RAWR so rand0m” type girl. But again…I’m already here…
We get to Starbucks and she gets me to order for her because “I just can’t handle that right now.” ok …We sit down and I’m already counting the minutes until it wouldn’t be rude to call it a night. We start talking, well, I start talking. The most I can get out of her is yes, no, or a slight laugh if I tell a joke. From talking to her like this, I find out she’s actually only 18, her profile said 21 (my age). Not a huge deal but I wouldn’t have gone out with her had I known that before.
Eventually, I ask her what she does. IMMEDIATELY, in one breath she screams out “I’MSOGLADYOUASKED I’M A PROFESSIONAL CLOWN WANNAHEARMYCLOWNLAUGH HHOOOOOOONNKKKK HAHAHAHHAHAHAHHAHA. I am mortified, the entire coffee shop turns to look, and she is oblivious to it. Suddenly she is no longer this weird shy girl. She starts telling me all these stories about her clown adventures. This goes on for probably 8 minutes. Everyone around is snickering and obviously listening in on it (not that they had much choice). She then tells me LOUDLY how her boss and one of her coworkers propositioned her for a three-way. She goes on to say, “Yeah I thought about it, but he’s 40 and I was 17 at the time so I decided not to. Plus, we were doing a child’s birthday party at the time, so it might not have been appropriate.”
As soon as she says that, a girl in the corner of the coffee shop lets out a stifled laugh. My date notices and goes beet red. I suggest maybe we should call it a night because I had an exam the next day. She saw through my lie but went with it. A few minutes later I realize tomorrow was Sunday. I drive her home; awkward silence follows for the 15-minute drive.
We arrive, I stay silent and don’t get out of the car. She sits there for a bit not saying anything. I go, “soooo…” What follows next is 100% true. She said this. I can’t ever forget it. She blurts out “Wanna come inside and do it while my cats watch?” Yeah…she said that. I stay silent for about ten seconds because I don’t know what to say. I eventually say “I uhh, don’t have any condoms sorry.” She gets the message and leaves. I hightail it out of there and never spoke to her again.
#99 Mistaken For A Cat Burglar
Suburban Chicago, age 16 or so, super-cold winter night on a date with the future homecoming queen, a sweetie who was game for anything legal for entertainment. I was feeling super broke driving in my parents’ ancient station-wagon with its not-great heater, and proposed that anything we did on our date, we do with money raised by redeeming bottles and cans we found around town. This was before homeless folk cornered that market.
We must not have raised much, because my next idiotic entertainment was “let’s follow a police car around, just for fun.” We found one and got behind it, not too close, but following. After a few blocks, the squad car took off like lightning, went around the block, and pursued us, lights flashing. It being cold in the car I had [winces] put on a knit cap/ski mask which had holes for my eyes, nose, mouth. I had never been stopped by a cop before, hadn’t had my license long, and thought it might be a courtesy [groans] to go see the officer in his warm car, so I promptly got out of my freezing wagon and approached the cruiser.
Out popped the cop, loaded weapon drawn, and I was spreadeagled against one of the cars. I did my best explaining to a not-amused cop, and got out alive; my date probablymas wet her panties. Next night, at the “youth center” there was different village cop there and I asked him if he’d heard about a pullover the previous night blah blah blah and he said “Yeah; kid near got offed; shoulda never rushed a cop… and the cops last night were looking for a cat-burglar in that neighborhood.”
#100 Musical Urinals
We went to a movie. During the movie, she got up to go to the bathroom. After she left, I thought I could run to the bathroom myself, and be back before her (for some reason, I thought it would be rude to leave her alone). When I came back to our seats, she was already there but I didn’t give it much thought.
I hung out at her place for a bit afterward, gave her a kiss goodnight, and went home thinking that I just had a pretty nice date. A week later, after she wouldn’t return any of my calls, I asked our mutual friend who introduced us what the deal was. Turns out that when I went to the bathroom, I accidentally walked into the women’s room.
I peed in the stall next to her, and she recognized the boots I was wearing. She was totally freaked out. When I finally got a hold of her and tried to explain myself, she told me she was moving to Turkey to get back together with her ex-boyfriend.
#101 Taking the Term “Blind Date” a Little Too Far
Not sure this counts since the date didn’t actually happen, but I was set up on a blind date. We planned to meet at a restaurant. I got there first and since it was a nice day out, I sat down on a bench outside the restaurant. He ended up calling me on his way over and I told him where I was sitting. He was still on the phone when he started walking up to the building. He took one look at me, hung up the phone, and walked back to his car. I tried to call him back, thinking something must have happened, and he didn’t answer. No more answers to calls or texts afterward.
#102 Cheaters Never Prosper
I knew my ex wife was cheating but didn’t tell her that I knew. Took her out for a dinner date and I casually asked questions about who she had been spending time with while I was at sea, she barely worked so she had to spend her time doing something. She failed to mention the guy that had been staying at my house for nearly two months, the guy she had to call the cops on just to get to leave because I was coming home in two days… soooo I slid her a copy of the police report that was filed for the incident and watched as she crumbled over the fact she had been caught, and I didn’t have to say a word.
Thanks to our friends at Factinate.com for sharing this article with us!