True Stories About the World's Most Bizarre First Dates

By Jake Schroeder
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Photo Courtesy: Pexels/Pixabay

For single people around the world, dating can be adventurous fun — or it can be pure torture. In the minutes leading up to a first date, a million thoughts go through your mind. When the date goes down, it could potentially lead to everlasting love, but it could also potentially circle you right back around to all the dating sites.

If some of your dating experiences have left you with some outrageous stories to tell, you certainly aren’t alone. Check out these crazy stories about bizarre first dates posted by various Reddit users. Some are almost enough to make you stop dating!

Dance the Night Away

I went out to dinner with a guy I had only met quickly once before. First, we go to dinner, which is okay, nothing special. It was a little awkward. At the end of dinner, he asks me if I like Dance Dance Revolution. I was like, "Yeah, sure." He then proceeds to tell me he is really good at it and wants to show me.

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Photo Courtesy: Jarkko Laine/Flickr

So, after dinner, he takes me to an arcade where he spends the next 30 minutes playing/dancing to Dance Dance Revolution while I watch. He never asks if I want to play, he just wants me to watch him. After that, I was ready to go home. I never went out with him again.


Real-Life Superman

It was in college. We were both very excited but never dated in high school. She was an amazingly kind girl who had never broken a rule in her life. I visited her at her house over break, and we had our first date while I was in town. We went to a gallery and were walking to a bistro when it started to rain. She loved old movies and musicals, so I started humming "Singing in the Rain." Soon, we were dancing down the streets of a small Pennsylvania town, arm-in-arm, having a wonderful time.

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Photo Courtesy: lincerta/Pixabay

Then I said, "I'd respect you a lot more if you twirled around that lamp post." Both of us were more or less willing to just do whatever the other wanted because we'd never dated and didn't want to screw it up, so she did it. There was a loud crack, and this 12-foot, cast iron streetlamp cracked around the base and began to slowly fall toward her. I dove and bear hugged the lamp post to keep it upright and wound up pulling it back over on me. (Boy, are cast iron lamp posts heavy!)

In this small town, this was the most exciting thing that had ever happened. The salon called 911, and it turned into a three-cop-car, ambulance and town lawyer affair. I was pretty banged up, but I did my best to play it off and rejected any treatment. As soon as the cops even looked at her, she started bawling, mainly because she had never done anything wrong in her life. For the rest of the date, she stared shamefully at her lap and didn't talk. It didn't work out.


Owl Take That

I met a girl online, and we agreed to meet up at her work on the day of our date. She worked at a local state park visitor center. So, I drove there, ready for our mini-golf date, but when I got there, she proceeded to take me into the back of the shop.

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Photo Courtesy: dannymoore1973/Pixabay

I wasn’t sure what to expect. She ended up letting me help her feed the barn owls and red tail hawk that they were rehabilitating in captivity in the park office. It was super cool, but I wasn’t expecting that at all.



Played for a Fool

I took this girl to a movie and then out to a restaurant. We started talking, but it was like talking to a brick wall. It's one thing to be quiet, but the idiotic stuff that came out of my mouth made me cringe. During this time, she kept checking her phone and putting it away without texting — just looking, so it didn’t seem like a big deal. We got our food and ate, which gave me a grace period to think about how to kindly take her home.

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Photo Courtesy: StockSnap/Pixabay

Then she started talking about going somewhere else for dessert. Normally, I'm up for that, but things weren't going anywhere. We finished, and I was waiting for the bill when she pulled out her phone and said she had to go. I said, "Okay, as soon as the bill comes, I'll take you home." She looked at me and said, "I'm okay. My boyfriend's here to pick me up," and then she just walked away.


A Kiss to Remember

I went to a coffee shop with this girl, and she ordered some sort of sugary drink. About halfway through, she got up and said she had to go to the bathroom. She came back after having very obviously vomited. I asked her if she wanted me to take her home, but she refused. So, she suffered through the rest of the date.

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Photo Courtesy: StockSnap/Pixabay

At the end of the date, she leaned in, and I didn’t want to be rude, so I tried for a nice, quick peck, but she went in hard core. It was kind of gross, but we did end up dating for a few months.


Cold as Ice

This guy invited me to go ice skating. I had never been ice skating before, and I wasn't very coordinated, but I didn't want to tell him that. We were skating for about 20 minutes, and I was feeling pretty proud of myself for doing so well. Then, BAM!

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Photo Courtesy: 995645/Pixabay

I totally wiped out and pulled him down with me, which caused him to elbow me in the face as he landed on top of me. My glasses broke, and I had a concussion and a black eye. I was too embarrassed to go on a second date.



Life's a Beach

While in college, I took a girl to get sub sandwiches, and we sat on a cliff overlooking a beach while we ate. I asked her if she wanted to go down to the beach, and she said yes. So, we go down the cliff and have to cross a small tidal basin to get to the main beach, which was luckily dry. We walked on the beach and messed around with some driftwood. After a while, I asked if she wanted to build a sandcastle, you know, because I’m awesome like that. She said yes, and I began digging with my hands — and almost immediately cut one of my fingers on a piece of broken glass buried in the sand.

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Photo Courtesy: sebastienross/Pixabay

I realized immediately that I was in trouble and let her know that I was injured. and we needed to leave. When we got back to the tidal basin, the water had come in, and I ended up giving her a piggyback ride across. The night ended with her and two of her friends trying to help me clean and bandage a 1-inch slice from the top of my finger down one side. I never talked to her again, and I still have a grain of sand in my finger that I can see. It reminds me of the story each time I see it.


Awkward from Beginning to End

I was 18 and in beauty school, and I needed to cut a guy's hair for a test. I didn't know anyone, so my friend had her ex-coworker come in. He was really nice, we hit it off and he asked for my number. I was pretty excited. It was the first time a guy had really asked me out, and he was cute.

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Photo Courtesy: paulbr75/Pixabay

We set up a time to go to a music/pop culture museum. On our way there, he criticized my taste in music, and we had a somewhat awkward conversation. When we got there, he looked at all the stuff he wanted to look at and ignored the stuff I wanted to see. In the interactive section, he did the activities and then moved on to the next one or cut in front of me when I wanted to try something.

After that, we went to a sushi place and ate. He said he would like to take me to a bar or something, and I mentioned I couldn't drink. He was puzzled, and I told him I was 18. I thought he was in his early 20s, and he probably thought the same of me. He was actually in his late 20s.

After dinner, he drove me home and told me about these gardens he wanted to take me to see, but by that point, I was so over it and just wanted to get home. He stopped the car in the driveway, and as I started to say thanks for the date, he said in a kind of creepy voice, "Yeah, I know of some gardens that are really beautiful, just like you!"

Without any warning, he literally attacked my face with his and kissed me so hard my head smacked against the window. I opened the door, practically falling out of the car, and just stumbled over my words to say goodnight and goodbye. I never saw him again.


The Need for Speed

My first date with this guy was simply dinner and a movie. On the way home, he decided to start driving 110 mph in a 65-mph zone. He got pulled over and subsequently arrested. His mom had to come drive me home. Needless to say, I never went out with him again.

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Photo Courtesy: tookapic/Pixabay

Into the Film — But Not into You

I got set up on a blind date by a friend's girlfriend when I was 15. After getting the girl's number, I rang her up, and we talked on the phone for like 2 hours, really seeming to hit it off. A few days later, we went out to a movie, and she ignored me the entire time. I mean, she literally ignored me — acted like I wasn't even there.

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Photo Courtesy: Pxfuel/Pxfuel

I tried to start up conversation with her a couple of times, but she gave me disinterested, one-word replies each time, so I just gave up. The movie ended, and we went our separate ways with nary a goodbye. To this day, it's probably the weirdest date I've ever been on.

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Don't Let the Door...Never Mind

When I was a senior in high school, I agreed to go on a date with a nice guy because I felt kind of bad for him. When he picked me up, he was super awkward and spent five minutes talking to my mom about his recent car accident. We were going to the movies, and I had told him he could choose the movie. He picked Rambo.

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Photo Courtesy: Eric Fischer/Flickr

I had never seen any of the Rambo movies before, and this was prior to me becoming desensitized by the internet, so I was fairly traumatized. Afterwards, we went to the store for some reason, and when we were leaving, he walked right into the glass doors because he thought they were automatic. Overall, it was probably the weirdest date I've ever been on.


Meet the Exit

I had a date who talked long and hard about how Meet the Parents was her favorite movie and how it was the funniest thing ever. By long and hard, I mean exactly that. She was going on and on for about half an hour at least. I excused myself to go buy a beer. Then I walked downstairs, bought a beer — and walked out the nearest exit, never looking back.

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Photo Courtesy: Pikrepo/Pikrepo

Couldn't Keep His Feet to Himself

I went to a movie, and the guy was determined to hold my hand. He actually took M&Ms out of my hand and forced his fingers between mine and wouldn't let go for the last hour of the movie.

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Photo Courtesy: Roman Craft/Unsplash

We got food afterward, and he would not stop trapping my feet with his. When we said our goodbyes, he gave me the longest, most awkward hug. On the whole drive home, I kept wishing I had "gone to the bathroom" at the movie.


A Whirlwind of Emotions

I went on a date with a guy I had met online. He wanted to meet for drinks, so I went to the pub and waited. He showed up 20 minutes late on his bicycle and proceeded to enter the bar and down two pints after giving me a point and a wink. I overheard him tell the waitress to "put it on his tab," and then he came over to the table with another beer.

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Photo Courtesy: StockSnap/Pixabay

He proceeded to tell me about his two boys — no mention of them in our previous conversation — and how his mom wanted to take them all to Disney World. He told her that would be too expensive — so he left his boys at home while he and his mom went to Disney World instead.

Then he proceeded to tell me that he rode his bike everywhere because after his sixth DUI, "those dumb cops" took his license away. He mocked me for drinking water, and then in his next breath told me that he could really see himself falling in love with me. In 20 minutes, I got about 10 words out, and most of them were me telling him I had to go. I later found out that he worked for a friend's father — and he was married.


Smell Ya Later

In college, I was set up with a friend of a friend. He had just finished baseball practice and needed to go back to his place to shower and change. I hung out in his living room in the meantime. The place had a weird smell, like an unseen animal lived there. The furniture also had a lot of stains.

Photo Courtesy: ilyessuti/Pixabay

When he was ready to go, I asked if he had any pets. He said no. I asked if his roommates had any pets. He said no. Okay, then. It brought to mind the Family Guy quote, "It smells like there's a cat, but I don't think there's a cat." He didn't get a second date.



Dodged a Bullet

My first date after an ugly divorce was with a cute girl named Heidi. She wanted to stop by a benefit that was being held for her friend, who had just lost her husband, and then we would go to dinner. I didn't see a problem with this, so I agreed.

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Photo Courtesy: mirceaianc/Pixabay

We walked into the bar where the benefit was being held and literally almost ran right into the guy who had cheated with my ex-wife. He couldn't grab his coat and leave fast enough. Heidi was confused, so I had to explain the situation to her. Just what you want to do on a first date, right?


Serving Up Some Ulterior Motives

I was probably 19 and had a huge crush on one of my coworkers. One day, he asked me to go to dinner with him after work. We went to a restaurant where another one of our coworkers also worked as a waitress, and he talked to her the entire time. They started dating a couple of weeks later. He totally used going out with me as an excuse to see her.

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Photo Courtesy: LuckyLife11/Pixabay

Should Have Stopped Him at the Fruit

He worked at a grocery store and brought me a box of spoiling fruit "because you're a single mom." We then went out to Big Boy, and we each paid for our own food. He asked if it was okay if he ran an errand, so we went to a music store where he spent an hour by himself picking out music.

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Photo Courtesy: Thomas B./Pixabay

He kept telling me all the things I needed to do to improve myself and was remarkably egotistical about how wonderful he was and how lucky I was to date him. We were both in the same group of friends, so I got rid of him by telling him I didn't deserve him — which I sincerely believed.



What a Twist!

When we got to the restaurant, I tried to hold the door for her, and she grabbed it with a look that said, "I can open a door myself." Small talk was stilted from the beginning. We had very different backgrounds and childhoods. I tried to describe the job I had at the time. In fact, I described it like 20 times, but she still couldn’t get it. I finally lost my cool and yelled.

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Photo Courtesy: sathyatripodi/Pixabay

I went to the bathroom, and she had already paid the check and said she just wanted to leave. That was 8 years ago. We had our second kid this year and bought our second house two years ago. We have been married for five years now.


Not the Christmas Miracle They Wanted

I was in high school, and on for a first date, I was going with the girl and her parents Christmas shopping. We went to eat first, and everything was fine, but as soon as we got in the store, something went horribly wrong.

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Photo Courtesy: Free-Photos/Pixabay

My stomach decided to reject the meal with no warning. I puked all over the floor in front of everyone as soon as we got in the store. It was the most embarrassing moment of my life.


Before Catfishing Was a Thing

I met her through an AOL chat room back in the day and drove to another state to meet her. She had a better 5:00 shadow than I did at 1 p.m. — just being honest, not judgy. We went to a family function, and her mom was not happy. The function had a Jerry Springer level of drama.

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Photo Courtesy: StartupStockPhotos/Pixabay

After talking to her for 15 minutes, it became apparent that she used a search engine to help her appear we had similar interests. As for the sprinkles on the sundae of awkwardness, I have touch issues, and when she touched my thigh to be flirty, I flinched.



Witnessing a Breakdown

We lived near each other, so I went over to her house to meet her so we could go to dinner. She seemed solemn, a little depressed and just totally uninterested. It turned out she was this way because she had recently broken up with a long-time boyfriend. She talked about him nonstop and started crying after dinner.

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Photo Courtesy: StockSnap/Pixabay

I was young and naive at the time, and I had no idea how inappropriate and wrong this kind of thing was. I kept thinking I was doing something wrong that was making the date go wrong.


Not an Illuminating Fellow

I went on a date with this guy who was as boring as a brick wall. He was super sweet, just didn’t have much to talk about. I literally got to the point where I had run out of things to ask, so I was like, "Sooooo, have you ever wondered how they make light bulbs?" I felt pathetic, but I swear this guy just didn’t know how to keep a conversation going.

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Photo Courtesy: Free-Photos/Pixabay

He Could Have Cracked a Tooth — Not!

I had a date with what seemed like a normal guy. He wolfs his whole meal down to the last bite and then starts to make this huge scene about how he bit something hard. The poor older woman waiting on us came over to see what was wrong, and he demanded the meal be comped.

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Photo Courtesy: Lucian Petronel Potlog/Pexels

I was mortified and gave her my card to pay for it. I dropped him and went home to my cat and TV.



Better Never Than Late

I had a date set with a fellow (based on an app) who was flying into my city. After he initiated the date by asking if he could buy me dinner when he arrived, he arrived late and asked if I would just come to his hotel room instead of going to dinner. I politely declined, citing a $50 surge-induced Uber ride to get to his hotel outside the city.

Photo Courtesy: sasint/Pixabay

I still foolishly agreed to go to dinner the next day. I showed up to the restaurant, and he wasn’t there. He showed up 45 minutes late — after I had already ordered based on the promise of him arriving shortly and telling me to go ahead and order. When he showed up, he asked how much an appetizer cost (<$4) and said, "Oh, no, thank you." We then talked for 15 minutes while I ate. I paid for my own meal, of course. Date over.


Dude, Where's My Car?

I met a girl on Tinder, and she drove over and picked me up since I live in Chicago and don’t have a car. She parked on a street, and we went to dinner and then a stand-up comedy show. The date was going well, and we were having a good time. We left and started walking toward her car — and don’t see it. She had parked in a no-parking zone, and it got towed.

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Photo Courtesy: Ruben de Rijcke/Wikipedia

It cost $300 to get it out of impound. My first reaction? "Damn, I’m an expensive first date..." I salvaged it, though (temporarily). We dated for two years after that.


I’ll Drink a Milkshake to That

I once went on a Tinder date with a guy who had to FaceTime his wife at exactly 8:00 to "prove" to her he was "going to bed," because she was away on a business trip. I sat there being super quiet in the back of a somewhat Riverdale-looking-type diner. There was no second date, but the milkshakes were good.

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Photo Courtesy: skeeze/Pixabay

Left Her High and Dry

I went on a date with a guy who insisted we have dinner at his favorite steak house. We ordered our food — I noticed he ordered the most expensive meal on the menu — and I suffered through some boring conversation with him.

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Photo Courtesy: jarmoluk/Pixabay

Suddenly, his ex-girlfriend walked in with her new man, and the two of them were shown to their table. They didn’t see us, but my date saw them — and broke down crying. They split up four months prior, and he was a mess. Our date suddenly turned into some kind of awkward therapy session, where he sobbed about how much she broke his heart.

Our check came, and my date said he left his wallet in the car. My eyes widened, and he said, "No, nothing like that! Don’t worry, I’m not gonna bail on you. You’ve been so good to talk to. I promise I’ll be right back." He never came back, and I had to pay for our $120 dinner and walk out alone.


Is There a Doctor in the House?

I got set up on a blind date with a coworker's nephew. I was around 19 at the time, and according to her, we would "really hit it off." Fast forward to the date, he bragged half the time about his gun collection as well as his entire family's redneck traditions and gun-toting heritage. It literally looked like his family could be on a Jeff Foxworthy TV special. Good for you, but that wasn’t my kind of thing.

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Photo Courtesy: Free-Photos/Pixabay

For the other half of the date, he thought it would be a good idea to list off all his illnesses and disorders. Seriously. He provided a full list, including the family history of diabetes, muscular dystrophy, M.S., developmental issues, etc. Who the heck reads off their medical history on a first date, especially a blind first date? You are trying to attract someone, aren’t you? Needless to say, I haven't agreed to blind dates since then.


The Moon Landing Happened, But Not a Second Date

I met a guy who was quite decent and normal at the beginning. Then we went to some pub, and I went to the bathroom, and, of course, there was a line. So, when I came back out, I told him as a joke: "It’s so funny that people fly to the moon, and they're not able to build restrooms so ladies have enough space."

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Photo Courtesy: stux/Pixabay

Uh-oh. For the next half hour, he wouldn't stop trying to explain that the moon landing was a hoax and a conspiracy by the Americans and that none of it ever happened. Eventually, I faked a phone call and got out of the horrible, stupid date.