These Dates Were Doomed From The Start

January 31, 2023 | Byron Fast

These Dates Were Doomed From The Start

Going on a date with a stranger is hard enough, but is there anything worse than knowing your date is doomed almost from the get go? These Redditors let loose on dates they went on that had a shelf life shorter than lettuce. Misunderstandings, crazy people, projectile vomiting and circumstances that no one—in their right mind—could have ever seen coming: they’re all here and more.

1. Not Up Her Alley

Last year I decided to text a cute girl that I had a class with the previous term to try to set up a date. She said sure, and we agreed to go bowling. When I got to the bowling alley, she was sitting on the railing outside the bowling alley waiting. I got out of the car and smiled at her. She said something that made me freeze. "Oh hey! I wasn't expecting to see you here”!

This floored me, but I couldn't think of a good response, so I acted like I wasn't expecting to see her either. I asked her if I should go inside and get a lane set up for us and she said, "Yeah sure, just hold on a bit...I asked another friend to meet me here”. When I asked who it was, she told me that it was her friend—that just so happened to have the same first name as me.

I went inside and paid for the alley and put on my shoes. I then put our three names in the machine. After waiting for 10 minutes or so, I got a text from her saying, "Where are you? I really don't want to be stuck here with this guy I used to have class with”! My instincts were right! She thought I was someone else.

She later came in and told me her friend—me—wasn’t going to make it. I asked her if she wanted to bowl anyway, and she said she didn’t like bowling.

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2. It Took An Hour And A Half

I love to talk and I'm good at keeping the conversation going. On one date, a girl and I took a really long walk, and she wouldn't stop talking. I waited to see how long she could keep talking for without me saying anything. I didn't say a single word for an hour and a half, and there were no silences. I honestly didn't believe that those types existed.

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3. I Blacked Out

About five or six years ago I met a girl that came into my work. I talked to her for a little bit and we seemed to really hit it off. She asked me if I wanted to go get dinner sometime. She said she'd come to pick me up and everything. That weekend we went out together to a restaurant on the other side of town. She was very interesting to me.

I really didn't tell her a lot about myself, because I kept asking her questions about what she was talking about. We'd just finished eating, I told her that I was going to get our meal since she drove us there. I had just given the waiter my debit card when disaster struck. I blacked out. This has happened two other times in my life, so it's not that common.

After my seizure was over, everyone in this restaurant was around me. People were holding my legs and arms. Everyone was scared, and someone had even called an ambulance. Usually, after a seizure, I’m in a bad mood. Everything seems different and it's kind of hard to explain. In this state of mind, I get up to my feet. I looked all over the restaurant for her, but I couldn’t see her.

I thought she maybe had gone to get help—but I was in for a rude surprise. Nope, she was totally gone. I made the EMS people wait for her as long as I could. I tried calling her. I didn't get out of the hospital until after midnight. I had to walk the whole way home by myself because we don't have public transportation in this town. I never heard from her again after that.

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4. It’s Been A Slice

A few years ago I met a guy at a bar who was born on exactly the same day as me. That seemed like reason enough to accept his offer when he asked me out. He told me to dress up very nicely as we would be attending an art gallery opening. I got all dolled up and when he came to pick me up, he was in a t-shirt and jeans.

Okay, maybe I'd misunderstood the attire requirement. We got there, and it was in a warehouse out in the middle of nowhere. It was actually an art gallery, but barely. Some of his friends were there, but he wouldn't introduce me to them and proceeded to chat with them and ignore me the entire evening. Meanwhile, I'm dressed to the nines and they're also all in jeans.

After we left, he asked if he could take me out to dinner. I figured, whatever, at least I'd get a free meal out of this awful evening. I was so, so wrong. We hit up a nice pizza joint and ordered a pizza. As I reached for a second slice, he just looked at me and said, "Wow! A second slice? Really? Jeez, you're a house"! So I ate the rest of the pizza.

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5. From Zero To Tears In One Date

I went out with a guy who wore the puffy shirt from Seinfeld. I swear this was the same shirt. I looked beyond that, or at least tried to, and continued with the date. He later had a meltdown in his car because I said hello to a male friend we had seen while we were at a coffee shop and laughed when he told a story to me.

He said my laugh was very flirty. What he said next blew my mind. He said that he shouldn't have “fallen for me” so quickly and wouldn't have if he'd known I'd “cheat on him so fast”. By this point, he was crying really hard the whole way back to my house. It was the most awkward car ride home ever. We never talked again.

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6. I Think I’ll Switch To The Salad

I went on a blind date with a woman who wouldn't stop picking at her scabs. She just sat there across from me picking away. I guess it was an unconscious thing. Then—to my horror—she made a pile out of them on the restaurant table. I excused myself to use the washroom and when I came back my soup was there, but the pile of scabs wasn't. No, I didn't eat the soup.

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7. It Wasn’t Love, Actually

This was a first date with a guy I met online. We'd had some nice conversations and decided to meet up one night for sushi. The night started off well enough, and I was really enjoying myself. About a half hour into the date, he starts getting a whole slew of texts and calls from who he claims was his dad. Being the slightly naive girl—it was four years ago—I shrugged it off.

So, the texts kept coming. He never bothered to put his phone on silent and checked every single text. He said his dad wanted to go work out with him. At that point, I had a good handle on what was going on. "Look," I told him. "If you aren't into me, that's fine. But have the guts to tell me instead of relying on your buddy to bail you out”. His answer left me stunned.

"Actually," he replied while standing, "it's a booty call. Thanks for dinner”. And he left. I sat there for a little bit, embarrassed because of all the sympathetic glances from the other patrons. The server brought the check over, but she leaned down to me and whispered, "I heard what happened. I took that jerk's order off so you only are paying for what you ate”.

That's when I started crying in the middle of the restaurant. I left the server a massive tip for her generosity and spent the rest of the night drowning my sorrows in Ben and Jerry's, and Love Actually.

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8. Three’s A Crowd

I met a girl online and she seemed reasonably attractive and fairly easy-going, so I figured, hey, why not? We met at a local coffee shop and chatted for a few minutes before a mutual acquaintance of ours happened to show up out of nowhere and began talking to the two of us. It turned out, they were both in AA together.

The two of them got to talking and I learned her long and sordid history of crazy stories involving booze. Then I heard the real reason for her wanting to date. I think her exact words were: "I'm trying to replace my boyfriend who passed this summer”. So, the guy decides to invite himself along for our date, neither of them asking me if it was cool for him to do so.

We end up driving to a bar—a fine thing for a couple of AA members to do—and the entire drive there they're playing the absolute most god-awful music on the radio I can think of. I'm in the back seat, this horrible music is blaring over the speakers while the two of them are chatting, and I'm thinking to myself: "Dear god, how can I find a way to get out of this”?

So we got to the bar and they proceeded to drink coffee and play air hockey while I tried to think of a way to leave. I ended up faking a cell phone call from my friend, saying I needed to go because she was in the hospital. The girl then proceeds to freak out at me for bailing on her during our date, at which point I just stared blankly at her for a second, blinked, and walked away.

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9. Bad Date Got Much Worse

Well, I was about 18 and working in New York City at my father’s printing shop. I had met this guy a few days before on a bus going upstate to visit my friend. I told my father I was leaving early to go hang out in the city with a friend and I was just gonna take the train home from there. I met up with the guy, and almost immediately he was weird.

Imagine that cartoon character Pepe Le Pew. Like he was trying to get all touchy-feely and huggy squeezy on the subway. Then he pulled out a disposable camera and asked if he could take my picture and tell people I'm his girlfriend. I, of course, said no, but I was a big people-pleaser and didn't want to hurt his feelings. So, I didn't end the date, but I couldn't wait to get away.

This behavior continued until we were walking down some random street and some scary-looking woman walked up to me and started getting in my face. That’s when I made a disturbing discovery. It was his girlfriend! I kid you not. We're in Midtown Manhattan, and we just happened to pass her by hanging out with friends. I tell her to get out of my face because I had no idea he had a girlfriend and am actually relieved she decided to show up.

I headed off down the street and he started to follow me and I just turned around and said, "Dude, you really don't want to do that. Trust me”. Since my train wasn't for a while I decided to go back to the office to wait. Well, the worst was yet to come.

When I got to the office I found my father cheating on my mother with the woman he hired to help with the filing: Bad date just got worse.

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10. The Russians Are Coming

So my date came to pick me up at my place in his little sports car. Then we went flying down the freeway at a super high speed, which was a little scary I guess. We went to lunch, and he was so nervous that he couldn't eat. He insisted on facing the door, and kept glancing over there like he was waiting for someone to show up. Needless to say, lunch was a little awkward.

As he was zooming me back to my apartment, he started telling me this story about why he had to face the door. He was supposedly some kind of secret agent who was likely being followed by Russian spies. He dropped me off, and his parting words were: "If you are approached by two men with matching red ties and black suits, run”.

I never saw him again. I assume it was the Russians.

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11. Funnel Cake Reappears

The summer after graduating from high school I went on a date with a girl I had been friends with for a while. We decided to go to a fair a few towns over. We walked around, ate some fried foods, and went on a ride or two. Things were going great, and many laughs were had. We then went on a ride similar to a Zipper or Salt and Pepper Shaker.

There was lots of spinning upside down and so on. That’s when I knew something was about to go horribly wrong. The funnel cake I had earlier decided that it did not want to remain in my stomach. With her sitting next to me, I commence throwing up...and then we flip upside down...and my barf comes right back at my face. I had enough sense to keep most of it away from her, as she emerged from the ride puke-free. I, however, did not.

We have now been dating for over 6 years, are currently engaged, and will be married next summer.

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12. You Had Me At Hi

This was, believe it or not, the only date I've ever been on. I met the girl online, and we planned to meet up at a museum. I got there and saw her a little ways away, so I waved. She looked my way, but then started walking away quickly. I then started walking towards her thinking she hadn't seen me, and was looking for me.

I caught up to her and said "hi", expecting a warm welcome. Well, I didn’t get one. She said she couldn't date me because I'm not her type. Now how did she get that just from the way I said “hi”?

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13. I’ll Be Right Back

Things were going good, I mean real good. The city was celebrating its glorious hockey playoff victory. The local heroes were one win closer to winning the Stanley Cup. Women were, shall I say, juiced about the victory. Booze was fueling the celebration and breaking down inhibition barriers. That’s when I saw her and my night changed.

We made some small talk until the bar was closing. I was so happy when she said she was house-sitting nearby and wanted me to come over and hang out some more. So, we were at her friend’s place and kissing and hugging. She asks me if I have any protection. I’m not the kind of guy who expects this to happen, so I don’t. She tells me there is a store up the road and gives me her keys to go get some protection. That’s when I made the dumbest move possible.

I went to the store and uh…about 30 minutes later…where did she live again? And oh yeah: I’d left my phone there.

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14. I Ate It All

I had my first date ever in ninth grade all planned out with a girl I really liked. When I was running through the plan with my friends, they reminded me how socially awkward I was, and that if I couldn't carry the conversation throughout the date, there wouldn't be a second one. So, being the smooth guy that I am, I decided to prepare myself for the date.

I tried googling "how to talk to a girl" and "conversation starters" an hour or so before the date. The only thing was that I was too nervous to memorize the questions, so I decided to write them down on my palm for future reference. For the date, she’d wanted to go for sushi. Of course, I told her I love sushi to convince her I am a sophisticated and worldly gentleman.

The truth was, I'd never had sushi before and as I looked down at my plate, I realized why. I was such a beginner that I thought what I now know as wasabi was guacamole. If you don’t know, wasabi is a combination of horseradish, fire and hades. So, I ate the whole chunk of wasabi and there I was, practically sobbing and oozing mucus out of my nose.

I decided to distract her with a tactical conversation starter. The only problem was, my palms were too sweaty, and all the ink had bled. I didn't notice while I was wiping the wasabi-induced snot storm off my face, so now my face was covered in ink and snot. I looked at her and saw that she was staring blankly at me wondering what to do.

I happened to catch a glimpse of myself in the reflection of a window and I was in so much pain and so mortified that I just started crying. We ended up having to call my mom to pick us up early and drove home in silence except for the oldies station my mom had playing on the radio. We ended up being friends later on in high school and laugh about it now. To this day, she thinks I was only crying from the wasabi.

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15. He Was A Naughty Boy

My good friend Vicki and her husband Will—who is a surgeon—are always trying to set me up: and I mean always. I usually turn down their offers, but they talked up this one guy named Ben. He seemed like a great guy: smart, a doctor, and his Teenage Mutant Ninja Turtle collection was bigger than mine! I really had no choice but to accept this blind date.

He took me to a pretty nice place for dinner, and I was kind of nervous, but nothing like super bad. Then he spilled his drink, and I’m pretty sure it was on purpose! I saw it! So, I was like What? I never, ever could have predicted what happened next. He started talking like a baby!!! "Ooopsie, I spwilled mwy dwink....I'm a bwad boyyy”. And I was like, "Ben? Are you ok”? I thought he was having some kind of a seizure.

But he kept at it. He continued with the baby talk, and then added something more: looking coy like a misbehaving child. Then he—I am not making this up—asked if "Mommy wanted to punish her bad boy". I was so out of there! I just got up from the table and walked out. He ran after—talking normally thankfully—and apologizing profusely.

I had to wait for my coat at coat check, so I was forced to listen to his apology. I assured him I wouldn't tell Vicky and Will about his kink. Then he went to hug me, and it lasted a little too long. I pushed him away and...well, there's no polite way of saying it…I felt something wet there, in his pants. I have no proof, but yeah, he did—against my leg. I just ran away and hoped I’d never see this guy again as long as I lived.

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16. She Was A Heavy PETA

This was a second date with a girl that I actually really liked. We got along great, and liked the same music. So the date was beginning, and we went to dinner and to see a movie afterwards. It was really no big deal: all normal fun stuff. She lived about 20 minutes away in a somewhat rural area, so on the drive back, we're talking, and listening to some music.

I was starting to really, really like her, and then it happened. A baby deer jumped out in front of my full-sized SUV. The baby deer basically exploded, and messed my car up. I stopped, and the date was awkwardly quiet. She looks over at me, and I quote, "What is your problem?! Blah, blah, blah...I'm a PETA member”. Then she hit me right in the face. She stepped out of the car and ran the other direction.

I sat in the car for about 30 minutes trying to figure out what happened.

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17. She Was At A Loss For Words

I met this girl on Yahoo probably about 10 years ago. We exchanged pics, and everything was looking good. We chatted online about various nonsense, and she suddenly asserted that she could beat anyone at Scrabble. I knew I was being baited for a date, so I challenged her to a game. Instead of playing online, she invited me over to her place. Well, I was in for an unpleasant surprise.

I get there and she looks nothing like her picture. Also, her "house" as she had called it is not a house. It is a trailer in a trailer park. She has no table on which to play Scrabble so we play on the floor. She has no drinks to offer me other than a bottle of Sam's Club bottled water. I obliterated her at Scrabble—twice. She then begged me to stay and sleep with her, which I did not.

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18. She Could’ve Just Broken His Heart

I met this totally unbelievably hot woman and asked her out. She accepted and decided she wanted to go ice-skating. Awesome! I'd been ice-skating once, when I was six and I thought: how hard can it be after a gazillion years? So we skated. I didn't fall once, well, until after an hour and it was time to clear the ice. I fell just as I was getting off the ice and low and behold I hurt my wrist.

After skating, she wanted to grab dinner. I didn’t want to say no, but my wrist was throbbing in pain. I ate using one hand through the entire dinner. No problem, it was almost time to leave and my wrist is getting worse and worse. That’s when she suggested a movie. Um? Sure? Ok, make sure she sits away from my broken wrist since it's a horror flick and she might grab my arm.

So the date ended at around 1 am and my wrist was still screaming with pain. I stopped by a friend’s place for some painkillers and he said, "Wow, I think your arm is broken”. So next stop, the nearby Emergency Room! Yep, I had three fractures on my radius. The silver lining? One year later we were married and lived happily ever after.

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19. He Was Majoring In Terror

I was in college and studying English. I’d just broken up with my high school boyfriend when a college guy—who was also an English major—asked me out for coffee and to study. We had been friends previously, so it wasn’t strange that we would hang out. While out for coffee, however, he started acting like it was a date. He bought my coffee and tried to hold my arm while escorting me around.

This also wasn’t a big surprise as he was an old-school gentleman who wore sweater vests and picked flowers for all the ladies. The part that made it a “fail date” was what happened when we sat down to drink, talk, and study. He slyly passed me a manuscript and told me he wrote it for me and had been too shy to give it to me while I had a boyfriend. He asked if I could edit it.

I obliged and before I could read it, he grabbed my hand and told me what a jerk he thought my ex was: and how I was better off without him. I recoiled, thanked him, and began to look at the manuscript. What I read made my blood run cold. The whole story was a revenge story about a boy who was in love with a girl. The girl in the story had a boyfriend who was a jerk. It sounded very familiar.

The story hero stalked the jerk boyfriend and eventually did him in. The murder scene was gruesome and incredibly detailed. He then, out of rage, also killed the story girl for not liking the hero boy all along. I don’t even remember my reaction. It was pure shock and terror. We did not talk after that. We eventually became friends again senior year, but I was always wary of him and didn’t like to be alone with him.

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20. This Deal Was Not Sealed

It was five years since I’d graduated and I finally asked a girl I had a crush on way back in high school to come to stay with me in Toronto for a weekend. We both grew up in London, Ontario, which is a small town outside the city. She took the bus up and we hung out all day. I showed her the sights, took her out for a nice dinner, and eventually returned to my place to watch a movie she had brought with her.

It’s finally the end of the night and we're heading to bed: brushing our teeth and so on. We got into bed and started snuggling up. I figure at this point the deal was sealed, so I leaned in for a kiss and she flew back and yelled:” What are you doing”!? I was confused, so I asked her what she meant. She said something like, I thought you knew. I was still in the dark and said that I had no idea what she was talking about.

Finally, she blurts out: "I'm gay"! I still had to hang out with her all the next awkward.

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21. Poor Ricky

It was a high school date and the girl offered to pick me up because she had just gotten her drivers’ license and permission to use her parents' car. This was cool with me as I didn’t like driving. So, she picked me up and a little ways away from my place, a raccoon runs out and she obliterates it. I even felt the thing thump hard right under my feet.

So, my date's eyes go wide and she stares straight ahead silently for the next few blocks until we get to a stoplight. I decided to break the silence with a joke and said "Poooor Ricky!—a reference to the cartoon character. Her reaction was seriously unhinged. She completely freaked out. She was screaming, crying, and even punching me. Finally, she just kicked me out of the car and burned rubber down the street.

After about a block she crashed into a parked car. Being a good guy, I ran to make sure that she was not injured. She wasn't, but when she saw me, she started punching me again and screeching about how it's all my fault that she ran into a car. I just walked back home and watched some TV. She never spoke to me again.

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22. Most Awkward Morning After Ever

When I had just turned 21, I was drinking at a bar and there was this cute older woman who was hitting on me and playing pool with me. We went back to her place that night, and we hooked up. In the morning, I was sitting on the sofa watching TV while she was using the bathroom. To my surprise, her son walked into the room.

To my further surprise: I actually knew him. We went to high school together and even played football once or twice. I never talked to her again.

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23. He Got Set Up

I was working at Gamestop—which I took way too much pride in at the time—and this cute blond came in and was looking at the used DVDs. She was trying to decide between season one of Buffy the Vampire Slayer or season one of Angel. Being a huge Joss Whedon fan, I offered my opinion on the matter, and we flirted a bit. I finally got the nerve to ask for her number, and surprise, she gave it to me. I called her the next day and made plans for dinner.

On the day of the date I woke up and couldn't stop throwing up. It turned out I had a stomach bug that was going around, but I decided to tough it out. So, I picked her up and asked her where she wanted to go. She points out a place across the street. It is the dirtiest, most disgusting hole-in-the-wall Mexican place I've ever seen.

I tried to be cool about it, so I didn't say anything and just went with the flow. I ordered my food, and she ordered the most giant burrito I have ever seen. I could hardly sit up straight because I was so sick, and this girl started to devour this burrito like she had never eaten before. Cheese and beans were dripping down her face, and sour cream was falling on the table. It took all of my might not to vomit.

Just as I was about to call it quits, this older woman—about mid-50s—and a younger man in his 20s came up and started talking to my date. I still can’t believe what happened next. She eventually introduced them as—get this—her mom and step-dad. I introduced myself while trying my hardest not to show my absolutely shocked face because of the obvious age difference. To my horror, they decided to join us for dinner.

Trying to be boyfriend material I agreed, and my date switched sides of the booth and practically sat on my lap. I spent the next 20 minutes listening to her mom talk about how they had to move out of their house because a ghost was haunting them. I put down 20 bucks to cover my and my date’s food, and went to the restroom to get away from the crazy.

When I came back, I was in for an infuriating surprise. I looked at the table and realized that the 20 dollar bill was missing, Sadly the restaurant bill was still there unpaid. I looked around for my money but found it nowhere. I could have sworn I paid the bill, but I wasn't about to accuse them of taking it, especially since I wasn't 100% sure I’d put it there. I should have checked my wallet, but I didn't want to flash cash around the restaurant.

So, I put $20 down again, and made sure I handed it to the waiter on his next pass. Being that I was lost in my head ignoring the mother, it was likely I’d imagined putting the money there. Finally the nightmare was over, right? Not quite. We were just about to leave and the mom asked the husband for his wallet to pay the bill for their huge meal. He delicately explained to her that he was without said wallet, and she replied that she hadn't brought her purse.

That’s when it happened. Both the old mom and the young stepfather both slowly looked up at me, and—much to my disbelief—asked me to pay for their food. I don't know why I said yes. Maybe it was because her daughter was hot, or because she was rubbing my thigh after knowing her for like 25 minutes, but I paid it. Forty more dollars!

So I finally took her home, and she begged me to hang out longer, but at this point, I just needed to get away. I waved and smiled from the car, and sped out of the dirty town she lived in. So, here is the real kicker. Before the date I went to the ATM and took out exactly $200 in twenties. I decided to look in my wallet in the car, knowing there should be 60 dollars missing, $40 for the parents, and $20 for my date.

There was only $120 remaining in my wallet. I screamed at the top of my lungs "I did put down the $20 and someone at the table had taken it”. I was mad for quite some time, but after I told the story to a few friends I realized it was pretty funny. I actually ran into the crazy woman years later at a party, and the craziness continued.

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24. She Built Him Up

I had a huge crush on this guy that worked at my local ice cream parlor. I only knew him from ordering my favorite ice cream flavor and blushing like crazy. Somehow I got the courage to ask him out, and he agreed to meet up at a bar near his house. I made it sound really casual. Like, "Oh, I'm just in the area”! The truth was I had planned it for weeks—months even.

He said he was just staying in to catch up on some reading, but he'd meet me anyway. I was so nervous that I was shaking and downing Budweisers to take the edge off before he showed up. While heading to the bar, I ran through a thousand different scenarios: what it would be like to finally talk to him and show him I wasn't a total idiot or awkward.

It didn't help that on the way into the city it poured for the like five minutes. I was actually out on the streets, so my clothes were drenched, my make-up was a wreck and my hair was a frizzy afro. But I didn't care, I had to see him. When I got to the bar and entered I just stared at him in shock. He’d brought along his girlfriend.

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25. Hit And Ruin

It was my first year of community college and I met a girl on an online dating site. Well, she looked a little different from her picture but meh—she was mildly cute and we were both kind of excited to get going on the date. Fast forward after a movie and deep conversation over an upscale Chinese joint—it was time to drop her off. Things were going really well: a second date was imminent.

We spoke for a bit in the car. It was almost one of those "we don't want the night to end" moments. Eventually, we started fooling around. Keep in mind, we were in the car and were located in a somewhat distant part of a mall parking lot. Suddenly a security guard's jeep lights flick on. It was night and you could easily see it from across the parking lot.

So, I do the only logical thing and flip it into first and take off. Unfortunately for me, the windows had fogged quite a bit. It was a total disaster. I realized far too late that I was about to smash into a concrete barrier with, ironically enough, a stop sign attached to it. She called her parents to come to give her a ride and that was their first impression of me. They didn't want her speaking to me anymore.

These Dates Were Doomed From The StartFlickr, Lee Haywood

26. The Cat Had Their Tongues

I went out with a boy from a previous job once. It was when I was incredibly shy, and I'd never been on a "real" date at 18. I didn't know how to behave. I'd thought he was extremely outgoing and talkative, but I guess he just played off my behavior and was twice as awkward. I think we said about five sentences to each other the whole night. We never spoke again.

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27. They Met Half Way

This happened to me before cell phone use was widespread. I was in college and there was this gorgeous girl showing some interest in me. Let's call her Sheila. The thing was, I had a girlfriend and most of the time I was with her when I saw Sheila on campus. So, we just said “hi” and small-talked a bit, which drove my girlfriend crazy with jealousy. I didn't want to dump my girlfriend, however, based on a purely physical attraction.

Near the end of the year, my girlfriend and I broke up. I didn't see Sheila anymore, and I assumed she had probably finished her courses. The following year, I'm studying in another city, so I called a common friend, let's call him Denny, and asked him for Sheila's number. After a couple of tries—this was her parents' home number—I had her on the phone. She said, "Yes, Denny said you were going to call. I don't know who you are, but we can meet halfway at the train station”.

So I took the train, very anxious, feeling a bit creepy, but well…this was my only chance to see her again. I didn't see her at the station so I waited. The crowd slowly scattered away, and I noticed a girl waiting at the other end of the station. I didn't know her and was getting a bad feeling. After a while, she came and asked if I was there to meet her.

It turned out that Denny knew another Sheila and thought I was asking for her number. The worst thing is she knew me by sight, but I had no memory of seeing her before. I had to decide quickly whether to go on with the awkward date or tell her the truth. Being a mostly good guy, I told the truth. She was really nice about it, and we laughed together. Then we went for a walk and talked for a while. She knew the other Sheila and said I should call her.

The following day I called Denny again asking for the other Sheila's number. He didn't have it, so I never saw her again. A few years later, some internet searching revealed the Sheila I didn't meet had become a famous DJ.

These Dates Were Doomed From The StartPexels

28. Snap, Crackle, Gone

I had a few awesome dates with a guy I met online at Geek2Geek and decided it was safe to tell him where I lived. I invited him over and we were enjoying the start of what was supposed to be an evening of movie-watching and talking when he suddenly bolted up from his seat. He then started walking around my apartment, snapping his fingers and oddly shuffling his feet around and swaying a bit.

He continued with this crazy person dance for about half an hour. Of course, I was wondering what was going on when he ran over to me, gave me a quick peck, and said he had to go. I asked him to stay a bit longer, but he refused. I was pretty disappointed. I kept asking myself if I had done something wrong, Things seemed to be going well.

We did continue to go out again, but it wasn't until a year later that he filled me in on what was really going on that night. Apparently, he had something inside him he really had to get rid of. The urge to rid his bowels of the demons within had hit him in a major way mid-evening. He’d started to become a bit flatulent, and he was trying his darndest to cover his emissions with the snapping and swaying around.

When he couldn't take it anymore, he flew at the speed of light to a Denny's about a mile down the road and used the bathroom. He was too shy to desecrate the toilet in my small one-bedroom apartment, and I don't blame him. Five years later, we still laugh about it, oftentimes snapping and dancing around the room like idiots, desecrating the toilets in our apartment with bold, unabashed fervor.

These Dates Were Doomed From The StartPexels

29. Miserable In Missouri

I went on a date with a girl that I’d met online. She seemed cute, funny, and all that. About 30 minutes into our conversation at the bar, we realized something awful. It seemed that we had gone to the same family reunions as kids. After talking about it further, we realized that we were actually fifth cousins or something like that. Man, I hate living in Missouri.

These Dates Were Doomed From The StartPexels

30. Kentucky Fried Christian

Way back in the day, I met a dude on Myspace. We chatted online for a while and decided to meet up for our first date. To my horror, he took me to a fast food place: KFC to be exact. If this wasn’t bad enough, while there, we met several of his male friends. The guy was an average-looking dude, nothing to write home about, and kind of short. However, one of his friends was a hottie and was giving me eyeballs.

I was trying to be nice and not notice this and gave my full attention to the date. All his friends were woo-hooing and congratulating him on "getting' a girl" This made me assume this was out of the norm. In spite of everything, things were going okay until he started asking me lots of questions about church and what my religious beliefs were. Being pretty Agnostic, I kind of just gave him vague answers, and tried to change the subject.

After our lousy fried chicken date with his bros, he took me home. In the parking lot, he reached under the seat of his truck and pulled out a copy of The Purpose Driven Life. He said, "I really like you a lot, but I don't like that you're not a Christian, so I got you this”. I'm already out the door and ready to call this a night, when he whips around the side of the truck and pushes the book into my hands.

Then he proceeds to attempt a sloppy kiss attack, which I escaped with quickness. I said goodnight and went inside. He texted me several times that night, to which I responded with: “I don't think we have much in common”, and told him there would not be a second date. He did not like this very much and proceeded to text me on the dot, like a stupid cuckoo clock every 15 minutes for the next few weeks.

These Dates Were Doomed From The StartPexels

31. She Took It Out On The Door

I'm not the best at “getting the girl”, but I think I know why. I'm a 19-year-old community college student who works at a video game store, has no car, and still lives with his mom. Anyway, I tend to not really worry about it because I used to try hard to impress girls and it just got to the point where I mentally said “forget it” and just moved on.

My attitude is: “if someone comes along and it happens, it happens”. Now, my best friend since the third grade told me a friend of his saw my Facebook pictures and thought I was cute. He proceeded to text me a picture of her and told me that I should meet up with her. Well, why not, right? So he gave me her number, I called her and we set up a date on a Friday at a pizza place.

We went on the date and everything seemed completely normal. We had a lot in common, and I thought something might come of this, but oh dear god how wrong I was. We finished dinner, and I took her home and said goodnight. She then proceeded to drop off all contact with me for no good reason. I wasn't completely heartbroken or anything. More like, "Whatever, another one down”.

After four more months of no contact at all, I was chilling at home, just getting ready for work and the doorbell rang. Through the peephole, I saw a familiar face: it was her. I immediately started thinking “how in the world did she find out where I live”? I didn't answer the door due to being half-dressed and just getting out of the shower.

The girl then proceeded to go ape crazy on my door. Like, pounding, screaming, punching, kicking and I swear once she might have even head-butted the thing. I think this because my door was metal and there were dents everywhere, including one that was about where her head would be. I didn’t let her in and she eventually left. Good riddance.

A few days later, she called my workplace and asked for me. Once again, I have no idea how she knew where I worked. On the phone, she tried to rope me into some rant about why she broke off contact and that she was sorry for almost bashing my door down. I knew this would go on for hours, so I made some excuse about the store being busy and hung up without waiting for a response.

I don't know what I did to make her secretly want to kill me, but it gets worse. She called me at about 10 pm the same day and asked me to meet her in the park. Now, this park had barely any lights, was nowhere near any kind of houses and the authorities barely ever went there. It's called the “dealer’s grounds” because literally all of them are there, selling their wares. I should have just said no, but curiosity had piqued me.

So I meet her by the swings—because swings are still awesome, despite me being 19—and she calmly explains that she dropped contact with me because she went to a mental hospital for months. Again, this is where I should have picked up and ran, but I was slightly interested in the rest of the story. Mostly I wanted to know why she thought she needed to beat my front door down. Doors aren't cheap, after all.

Anyway, she says she found my name in the phone book and called our house, but the line was disconnected, so she just went to the address she found after a lot of Googling. When I didn't answer, she told me she thought I hated her for not talking to me for months and wasn't trying to break the door down, but rather she was punishing herself for being an idiot: her exact words.

I was silent for a little, then said everything was fine and not to worry about it, but I don't really want a relationship at the moment. I mean, who would after that? She then throws herself on me like a rabid zombie, and tries to kiss me. I push her away and get off the ground and start walking, very fast, away from her.

She then tackles me, and I mean really tackles me, to the ground and she pulls something out of her coat pocket. It was a syringe. Full of what, I have no clue. I wasn't gonna stick around to find out, so this is the one time I hit a girl in my entire life. I shoved her off me yet again. I then booked it back to my house.

I never saw her again. I'm guessing she gave up.

These Dates Were Doomed From The StartPexels

32. Left On The Bleachers

I was in 10th grade and this guy I really liked invited me to a soccer game. This was only about the second time we ever met. He ended up seeing his ex-girlfriend there and talked to her nearly the whole time. I sat in the bleachers alone trying to call my parents to come to pick me up, until some random guy from the marching band came over and played me a "song" on his trombone to make me feel better. I think he'd been playing trombone for maybe two months at the time so it wasn’t very good.

These Dates Were Doomed From The StartWikimedia Commons, Derek Bridges

33. She Didn’t Even Like Calvin

First off, I should mention I've never been on a successful blind date. I think my friends purposely try to torment me by finding these girls. Here’s the one I remember as the worst. She was a vegan, although no one mentioned that to me. I guess she didn't think it was important to mention that to me when I told her I'd cook us dinner and asked if she was picky. So, I spent a good hour making an amazing Italian dinner: none of which she'd eat.

So we went to a vegan restaurant, and I ended up eating what equated to grass, while she told me about how our "meat culture would be the end of us all.'' We then went to see a movie. Midway through the movie she told me: "let's go, cause I want to show you something". I'm thinking: okay finally things are starting to pick up a little. We go back to my place and she runs up the stairs to my room.

I told her I'd be up in a moment and ran to the bathroom to do a quick prep for some very intimate playtime. I walked into my room with my shirt off and a grin on my face. She was sitting at my computer and had a website open. I ventured over to see what it was. It was about women's liberation and how horrible women are depicted in modern movies. Not at all what I was expecting.

For the next 10 minutes, I’m nodding my head pretending to understand what was coming out of her mouth in hopes that I might still get laid. She was really cute after all. After she thought she’d convinced me of whatever she was saying, she saw my old Calvin and Hobbes poster and said, "I never liked that comic". That was the last straw and I asked her politely to leave.

These Dates Were Doomed From The StartPexels

34. He Was Too Prepared

This was the first date I had with a woman I met online. She was attractive, and I was really excited. As I'm driving her back to her car, the glove box of my car suddenly pops open and a box of Trojans falls in her lap. She was clearly not impressed. No, I’m not a player. Here is the reason why my glove box was full of prophylactics.

My buddies were so excited that I actually had a date—it didn’t happen that often. So as a joke, they’d given me the box of Trojans. Like an idiot, I had thrown them in the glove box of the car. I wasn't planning on getting any on the first date, but I forgot I had them in the glove box when I went on the date. Honest!

These Dates Were Doomed From The StartPexels

35. Do You Hear Wedding Bells?

I met this girl on a dating site. We exchanged pictures, talked for a week or so and set up a date. When I showed up at the bookstore for our date, I’m facing someone who does not look at all like her picture. She was way taller than I thought—and built like a football player. She was also very masculine and covered in tattoos. I'm a nice guy, so I follow through with the date.

She wasn't crazy from what I could tell at the time. I walked her to her car and tried to hide my terror of what I saw in her back seat: a wedding dress. The hairs on my neck stood up and my Spidey-sense was deafening. So I asked, "what's the wedding dress for”? She said, "well...I thought if the date went well”… I waited for what seemed like forever for her to smile, laugh or anything that would tell me she was joking, but nope. I said nice to meet you and speed-walked myself to my car.

These Dates Were Doomed From The StartPxhere

36. There Was Dirty Laundry Everywhere

So, I had recently dumped my girlfriend, and she was coming over to take some of her stuff out of my apartment. The thing was, this was really bad timing. At the same time, I was supposed to be meeting this really cute server at her job to pick her up after work and take her out. So, I foolishly left my ex at my apartment and went on my date. This was a big mistake.

So, I show up at the pizza place where my date worked, and she tells me to hang out for a few minutes while she clocks out and all that, and I sit down at a table. At that moment, my ex walks in, and sits down across from me! She had followed me! So, I see the other girl come out from clocking out, give me a funny look, and she just sits down at the table next to ours.

At this point, my ex is grabbing my hands and literally begging me to give her a second chance. I was trying really hard to be nice, but firm. She started crying, and my date finally got up and walked away. I don't know what she must have thought hearing my ex spill all our dirty laundry right in front of her. My ex didn't have any idea what was going on, and never gave my date a second look.

Needless to say there was no second date.

These Dates Were Doomed From The StartPexels

37. Honest Was The Best Policy

I went on a date with a girl in college who I really wanted to sleep with. Turns out my attraction was only physical, and I couldn't even make it through dinner without wanting to kill myself out of sheer boredom. I finally just decided to be honest and said: "I'm sorry, I don't want to waste your time or mine. This isn't going anywhere" I then got up and left to go meet my friends at the bar.

These Dates Were Doomed From The StartPexels

38. There Was No Gray Area

In high school, I went on a date with a guy some girl from my soccer team knew. He seemed like a nice guy, so we went and had coffee at this place in a mall. We were sitting there, and the conversation was alright and then during a moment of lagging conversation he came out with: "I hate couples with people of two different races, it's just not right".

My response was: “Um, I think it’s time to go”. Needless to say we never went out again.

These Dates Were Doomed From The StartPexels

39. She Wasn’t Clear

I once went out with this girl and we were having a good time. We were drinking pretty heavy—mostly Everclear and juice. She suddenly started throwing up like crazy. I was like: "Are you OK? Are you OK”? Her reply was more than disturbing.

She told me: “It's not the drinking, it's because I’m pregnant and have morning sickness”. What is wrong with people?

These Dates Were Doomed From The StartFreepik,stockking

40. He Disrespected The Gayborhood

I'd had two dates with a fellow I met on OK Cupid that went really well. Both dates had been in his neighborhood and had led to hot makeouts, couch snuggling, and him making dinner for me. I thought we were both fairly interested in one another. On the third date, it was his turn to make the trek to my neighborhood, and I cooked a pretty fancy dinner for him.

He was late to get to my place, and complained about the lack of parking, and then complained about the neighborhood. You see, I'm bi and I lived in Boystown at the time, so yeah it was gay as the day is long but he knew this in advance and his distaste for the fabulosity really turned me off. Worse still, when he finally stopped complaining, he didn't have anything to say at all.

Somehow, the charming fellow from dates one and two had completely disappeared! We sat in awkward silence when he wasn't being condescending or critical. After about an hour and a half he suddenly—and very quickly—bolted. Neither of us contacted the other again. It was bizarre, especially since we'd gotten along so well the first two dates, and I was ready to put out.

These Dates Were Doomed From The StartPexels

41. Bi The Way

I was hanging out at my house with this guy I had met from work and really liked. We were asking each other questions, just getting to know each other more outside of the work setting. At one point he gets a cheeky look and asks me if I've ever kissed a girl. I’m into both guys and girls, so I reply yes. He looks surprised at how nonchalantly I responded, and pressed further.

When I told him that I was bi, he was silent for a long five minutes. He then silently got up, and just left. Two days later he called me to ask me out on another date. It was weird because he was acting just like nothing had gone wrong. I told him I'd rather gouge my eyes out with a rusty spoon than go out with him ever again.

These Dates Were Doomed From The StartPexels

42. He Wanted To Lead

I am a 20-year-old female and this was my first date—and incidentally my only date so far. You see, I’d recently lost a ton of weight, and I decided to try some internet dating. One of the guys who asked me out said that he had Asperger’s. The thing was that I was socially awkward, so I thought that made us a perfect couple. Boy, was I wrong about that.

So we walked around a little bit together. Now, I'm a terrible conversationalist, and he kept getting frustrated that neither of us could keep up a conversation. I felt terrible, but with every passing minute—the date was less than an hour, I think—my already below-average ability to talk waned. Eventually, he sat down and asked me what he could do better.

I told him that it was my fault, that I'm not used to talking to people, let alone dating. All he kept saying was: “Stop it, I’m the man and it is my responsibility to lead the date”. I felt so terrible.

These Dates Were Doomed From The StartPexels

43. He Got Bounced

I had gone on a really great first date with a guy I had met on the internet. We decided to meet up again, and he suggested we meet when I got off work at the same bar as the first date. I got to the bar and was waiting for him to arrive, so I ordered a drink. Ten minutes later I saw him walking over to me and the bouncer was following closely behind him.

He got to my table and the bouncer said: "No dude, you are still kicked out of here from earlier" and roughly walked him out. So I just stayed and finished my drink.

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44. Couldn’t Find The Washroom

When I was in college, I went on a date with a coworker. We went to see a movie and then to a mutual friend's house to drink. We decided to go back to her parent’s house to chill after. Since I was quite inebriated, she agreed to let me stay the night. Apparently, in the middle of the night, I got up and peed on her dog’s bowl and all over the kitchen floor.

She cleaned it all up and told me about it the next day at work. Four years later: we got married.

These Dates Were Doomed From The StartPexels

45. It Was Immortalized Forever

Back in college, I was invited to an ice rink with a girl I liked along with some of her friends. I did not know how to ice skate, and I did not pick it up very quickly, but I wanted to try and impress her somehow. Well, I hugged the wall the whole time and made a fool of myself. The highlight was when I saw a flash of light as I fell in front of a group of people.

It turned out I had fallen right at the moment someone took a picture so my failure was immortalized forever. She took me back to my apartment and ended the relationship before it began. On a lighter note, the woman who is now my wife was at that ice rink on that night. We didn't realize we were there at the same time until a year or two into our relationship and she exclaimed, "You were that guy who couldn't ice-skate! Yeah, she didn't seem that into you”.

People talking on the streetFreepik,wayhomestudio

46. She Could Do So Much Better

I went out with a musician on a blind date once. He talked about himself non-stop for an hour and when I mentioned casually that I like things like Reddit, Star Wars, and fixing computers he called me weird. He said, "You can't be a computer nerd with that pretty face. You could do so much better”. I told him that I completely agreed that I could do better things with my time. I then stood up, excused myself, and left.

According to a mutual friend, the guy never understood what I meant by that comment and was super angry that I left him with the bill, which was a couple of bucks for a soda. I don't usually expect guys to foot the bill just because they're guys, but I later explained to him that if he was going to ask me out and then insult me, he's lucky he only paid for a soda.

These Dates Were Doomed From The StartPexels

47. Don’t Play It Again Sam

I had been in a relationship for two years in high school. We broke up, and I just started dating a distant friend of the ex. We had been dating for like two weeks, which was mostly just me driving him around and buying him breakfast before school. He had me in his car in the parking lot after school one day because he said he had to talk to me.

So, I'm sitting there, and he says, that he wants to sing me a song. He then pulls out this piece of paper with the lyrics to Kasey and JoJo's "All My Life”. He starts singing the "baby, baby, baby, baby, baby" in the beginning. I suddenly yell at him to stop because that was my ex and my song. His reaction was unforgettable.

He gets embarrassed and ends up eating the piece of paper. Like, crumpled it up, put it in his mouth, and swallowed it. It was so weird.

These Dates Were Doomed From The StartShutterstock

48. She Was Traditional

I once went out with a girl, and five minutes after sitting down at the restaurant she says, "I'm a little old fashioned and think guys should always pay for everything when they are dating a girl”. I had planned on paying but having her so blatantly state that so early on, I was pretty angry and realized the date was already a total bust.

Since the date was going nowhere, I decided to have some fun. I told her that the reason that guys traditionally paid for everything was that back in the day, women weren't allowed to get real jobs. So, to further this return to the “good old days”, I told her that I would also be ordering for her since that was traditional too.

These Dates Were Doomed From The StartPexels

49. Like Jekyll And Hyde

I once drove two hours to see someone I had been talking to for almost a year online. When I got there, I was in for a horrible surprise. I found a much younger man than he’d said he was. Also, he was living in the back room of his parents’ house. It was like a back porch, and his bed was a couple of blankets and pillows on the floor next to the washer/dryer.

Once we were off the computer and in real life, conversing with him was like talking to a wall.

I had arrived at his place really late, so I went to sleep when I got there. The next day we went to his local—to be honest quite run-down—mall and he met up with a friend and ignored me the entire time. I eventually got annoyed and left. When I got home, he talked online like he did before we met: all sweet and saying he missed me—nothing like he was in person.

I told him I wasn't interested and every few months for the next year or two he would try to talk to me. Ugh.

These Dates Were Doomed From The StartPexels

Sources: Reddit,

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