The Worst First Dates Ever

May 16, 2022 | Violet Newbury

The Worst First Dates Ever

There is nothing like the excitement of a first date: the planning, the primping, the butterflies—all good stuff.  However, sometimes, when the day comes, things don’t go as planned. The other person turns out to be a total weirdo, or the date takes a seriously disturbing turn. Here are some stories of first dates that went so wrong, the only thing right was to turn around and say goodbye.

1. She Got The Point

I decided to meet up for coffee with a girl that I had been talking to online. We talked for 45 minutes or so about normal first date topics like family, travel, etc. She then asked, "Where did you do your undergrad"? I had a pretty good job, but that question set the bar pretty high for a guy who didn't go to college.

She was not only assuming that I went to college but was also assuming that I was taking part in some type of post-graduate school. When I said that I went to technical school and then straight into the workforce, her reaction was brutal. She looked at me as if she had never heard of such a thing. Apparently, I didn't pass all of her minimum requirements to be considered human.

After a brief pause, she broke off her shocked stare, placed her hand on her forehead in a fashion that covered her eyes, inhaled briefly, and followed it by a valley girl, "Eew"! She took her phone out of her purse and whispered to herself as she typed, "He...didn't...even...go...". I then saw her left thumb hold the shift key as she deliberately pressed the exclamation point key not once, not twice, but three times.

She pressed a few more buttons on the phone, presumably sending this text message to her friend. She put the phone away, looked at me, and after taking a deep breath, said, "Well, that is okay. Not everybody is capable of going to college". She put on a fake smile, followed by an awkward laugh, and just stared at me awkwardly.

I couldn't believe that she had reacted so rudely to something and then tried to act as if it didn't happen. Perhaps she still believed that—like a child playing hide and seek—if you covered your eyes, you would disappear. After staring at each other awkwardly for a few seconds, I finally broke the silence by saying, "Wow, okay. So, yeah…I, um, guess it is about time to get out of here".

I stood up and took my trash to the garbage can, and she followed me out the door. I turned and began walking down the street, and she followed closely and said, "How far away is your car"? This girl was expecting a ride! So, I stopped, turned around, and said, "Oh, I am about a block this way. Where did you park"? She replied, "Oh, I took the bus here. I don't have a driver's license".

I am usually not a rude person. I was going to just walk away and let that be that, but I just couldn't pass up the opportunity that had presented itself. I looked her right in the eyes and said, "Eew"! I pulled out my cellphone and typed, "She...doesn't...even...have...a...license", and I added three exclamation points.

I then put my phone away, looked up at her, smiled, and said, "That's okay! Not everybody is capable of driving a car! Lucky for you, the bus stop is right over there. I hope you don't have to wait too long"! I wish I had taken a picture of the look on her face as I walked away. It was priceless.

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2. I Wanted To Break Away

A regular customer of mine who knew I had a new bike asked if I wanted to go cruising with him, later on that week. Happy to have someone to ride with, I accepted. We met up at my work, grabbed a few bottles of water, and then we were off. Halfway through the ride, we stopped, grabbed a coffee, and chatted for a minute.

We continued to ride and wound up at this beautiful part of the local beach I didn't even know existed. Things began to feel a tad bit off at that point, but I didn't think much about it. We parked the bikes and chilled out on a log overlooking the water; there was no one else in sight, which was rather odd timing. There was a long moment of silence.

I looked away to gaze at the scenery and I felt a hand on my leg.  When I looked back, he planted a wet one right on my lips. I stood up and screamed out of shock. Embarrassed, he jumped on his bike and sped away. It took us an hour to get there, but since I didn't even know what part of the beach I was at, it took me three hours for me to get back to my car. I had no idea he thought this was a first date.

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3. He Was On Another Planet

I was on my first blind date. I met this guy at a bar. We sat drinking and chatting for the first 20 minutes, and everything seemed cool. Then, we somehow started talking about speeding fines.  He told me, “I never have to pay speeding fines”.  I asked him why, so he whipped out a keyring with a picture of an eye on it.

It meant he was a Freemason. It was pretty odd, as I was fairly sure they're not supposed to go around telling strangers about it. He was wearing a kippah, so I asked him if he was Jewish. He said, “Sort of, but I know the truth”. So I asked him what “the truth” was, at which point he unleashed a colossal stream of pure crazy. 

He told me that the Earth was originally populated by a race of four-meter tall aliens who created humans to work as slave laborers in their gold mines. These aliens flew back off to their planet for some reason, but left their reptilian spawn living in underground cities across the globe, ready to recolonize at some point in the future.

The humans built Atlantis but did something to anger the aliens, so it split up and sank, and the people had to go and live elsewhere. After this happened, the Jews arrived on Earth from their planet because they didn’t have the required level of magic abilities and needed to relearn them on Earth.  The Jews built the pyramids, which are, in fact, home to their alien rulers, and were allowed to return to their planet when they reached a certain level of awareness.

The Holocaust wasn't a genocide. It was actually a mass exodus of super-aware Jewish people from this planet to their homeworld. Meanwhile, the reptile monsters still live beneath the Earth's surface and occasionally walk among us disguised as people. They control things like the UN, the Freemasons, and the Illuminati so that humans stay blind to their existence.

Finally, at the end of the year, the recolonization of Earth by the aliens was going to begin again. I would have assumed it was all a massive joke, but he kept getting angry when I said it sounded like a story from The X-Files crossed with Scientology. The funniest thing was that he actually believed I was going to let him come home with me at the end of the evening.

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4. Love At First Sight

I was going on my first date with someone I had met online. We had been talking for about two weeks before we met up. We went to dinner on our date. He wasn't super talkative, and it was mildly awkward. Then, when he was dropping me off, I gave him a hug good night, and he took that opportunity to whisper in my ear, "I love you".

I didn't know what to do, so I laughed, assuming he was joking. He wasn't.

Not What It Looks Like FactsPixabay

5. What In The Sandhill Happened?

I met a girl in a college class and noticed that she was looking at golf clubs on eBay. Being a golfer myself, I figured it was a perfect conversation starter and went with it. After we exchanged numbers and some conversation, we had a golf date at a local country club for the following afternoon. The first few holes went well, but then the 7th hole happened.

I was about 230 yards from the green, so I pulled out my 3W club. I saw a pair of sandhill cranes that were only about 150 yards down the fairway, so I paid them no attention. I took my swing, and, to my surprise, the ball was a low line drive that got no more than a few feet off the ground. Also, to my surprise was the fact that one of the birds was in the way of the ball.

It was a direct hit to the neck, and the bird went down for good—and that’s not even the worst part. Sandhill cranes mate for life, so when one passes, the other will sit there for hours crying for the other one. It was sad, but little did I know my date LOVED these birds. The look on her face was horrific. She broke down in tears.

We played the last two holes, exchanging only a mere few words. I didn't hear from her again.

Worst First DatesPixabay

6. See Ya!

I had been texting with a guy for months late at night.  He offered to take me out for drinks, and on a lark, I accepted. I was rebounding off another man, and my standards were pretty low. His friend “just so happened” to be drinking at the same pub we went to. They stood at the bar, not ten feet from the table we were sitting at, and every time this guy drained his drink, he would go up to the bar and chat with his friends.

This was obnoxious enough, but on his third little chat, they were all plastered and started talking about me—my looks, my accent, whether I would be any good in bed, etc. I was ten feet away and I could hear their conversation. He was so distracted moaning about how this American girl—me—was not as easy as he'd thought that he didn't even notice me walk by him and out the door.

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7. Looking Out For A Friend

I was at a bar with my SO and her roommate when I saw this little dude dancing wildly with a woman who looked uncomfortable. The woman later started talking to my SO's roommate and said it was their first date. She said that he kept grabbing and touching her. He literally stepped in between the girls as they talked and tried pulling her to the dance floor.

She looked terrified.  She said, "I need to leave", and ran for the door. I normally wouldn't step in, but something told me to. Luckily, I was quite large, so he backed off, but the look on his face was an angry/insane look I hadn’t seen in a long time. He went back through the dance floor and made his way to the door.

An officer was standing nearby, and I didn't even have to say anything. He saw the woman run and was already on the radio with the officers who stood out front. They had it under control.

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8. This Date Blew

I started talking to a girl on OKCupid. She was pretty, seemed down to earth, liked Skyrim and Game of Thrones, and generally seemed cool. We planned to meet for dinner. I got to the restaurant at around 7 PM. As I was sitting outside, I heard, "Hey"! I looked over and had to do a double-take. This was definitely the girl I was talking to, but she was so very different in real life than she was in her pictures lead on and not that great looking.

She was wearing a Pokémon shirt too small for her. I wasn't going to back out, so we started talking and went inside. I noticed when we were sitting down that she never closed her mouth and breathed loudly out of it—she was a mouth breather. Not only that, but she would just stare at me while mouth-breathing—it was so weird.

When we were choosing appetizers, she claimed that she couldn't eat mozzarella sticks because she "self-diagnosed" herself with Crohn's disease since cheese made her gassy. Then she started insulting our waitress, saying, "I bet she likes Twilight and Jersey Shore. I'm probably the only girl who likes gaming around here. I'm real". And somehow, it got worse.

She kept making grunting noises and heavy breathing noises, and at one point, she got sauce on her chin and never wiped it off. When the waitress brought out our dinner, my date said, "A wild steak appears", and the waitress and I just sort of looked at her. It was awkward. Towards the end of the meal, she passed gas really loud and started crying because she was embarrassed about it.

Everyone was looking at us, and I just sat there.

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9. If She Only Knew

I was on a first date with a cute girl. Everything was going really well when, suddenly, I was overcome with a violent case of Montezuma's revenge. I calmly excused myself and walked to the bathroom as fast as I could without it being obvious that I was sprinting. I managed not to destroy any of my clothes, but it took me about 10 minutes to clean up the bathroom.

I also had to douse myself with the air freshener spray they had in there. When I came back, my date was gone, and the waiter was standing next to the table. He had asked my date where I went, and she started crying and stormed out. She never returned my calls or texts after that.

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10. She Didn’t Want S’more Of That

My roommate's girlfriend was a dancer at a club. He and I would go on slow nights, get a couple of drinks, and she and her coworkers would sit and hang out with us when they didn't feel like being pawed at. During the course of one of these hangouts, I struck up a conversation with a dancer who turned out to be extremely well-educated and a would-be symphony composer.

She was also ridiculously hot, and we just clicked. It took a while since we met at the club, but I eventually got a date with her. We started our evening at a local coffee shop that was famous for having little s'mores platters with flaming cans to toast your marshmallows. We got a couple of lattes and a s'mores platter and proceeded to flirt.

Things were going swimmingly—until total chaos broke loose. One of the marshmallows I had on a skewer caught fire. I had a mouthful of scalding hot latte at the time, so I panicked and just waved the marshmallow to put it out. It promptly sailed through the air like a sticky, flaming meteor and landed on her lap. She looked down with horror as her velvet pants caught fire. She shrieked.

I wanted to throw a glass of water on her or blot it out with a napkin, but the only napkins I had were paper, and I had no water—just a scalding hot latte. She looked at me, panicked, and said, "Do something"! So, I did what I could. I doused the fire with the scalding hot latte. She went to the bathroom and returned with scorched pants and burns on her thighs. She said, "Let's call it a night". I did not get a second date.

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11. Stop Whining!

I met a guy at a friend’s party.  We had been texting for a few weeks, and he seemed awesome.  We decided to go on a date to some small fancy restaurant. He picked me up and spent the entire time driving to the restaurant complaining about his day. We got to the restaurant too late, and it was closed, so he complained about that too.

His friend called him while we were looking for a new place. He answered and complained about how the date was so bad. We ended up eating at IHOP. All the while, he was still complaining about how terrible the date was. I know he meant it was terrible in that we didn't get to go to the other restaurant and ended up at IHOP.

However, in my opinion, a date is good or bad based on if you have fun with the other person, so I took it personally. At the end of the night, he dropped me off and told me he had a great time even though it was a terrible date, and that he would like to see me again. It didn't happen. Maybe if he hadn't whined the whole time, I could have had fun as well.

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12. This Date Took A Bad Turn

I took a co-worker of mine to a baseball game. We had a great time, got pretty tipsy, and took the subway back to my house to close off the night properly. When we were going through the exit turnstiles, disaster struck. She got her toes stuck under them. She started freaking out and yelling at me angrily, saying her toes were broken/fractured until the ambulance got there.

When the paramedics arrived, they un-trapped her toes within three minutes. We drove 30+ minutes to the hospital and were stuck there for hours with her badgering me about how much pain she was in as she sat in a wheelchair. The X-ray came back at 6 AM—with a twisted surprise. We found out there was absolutely nothing wrong with her toes.

I paid for the expensive cab ride across the city and put her to bed in my guest room, so I could wake up two hours later to go to work.

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13. He Was Not A Good Sport

I went to a large university, so it was hard to meet people in class. Luckily one semester, I had a couple of small discussion sections and hit it off pretty well with a guy in my Shakespeare class. We decided to go on a date to a local cafe. He and I had nothing in common outside of liking Shakespeare. He only talked about weightlifting and "bulking up".

His only hobby was weightlifting, which I knew nothing about, although I asked a lot of questions. He started berating me for not weightlifting and asked what sports I played in high school. I was a cheerleader and ran track, which he said "didn't count" and that he "couldn't date a girl who didn't do sports". I can run a half marathon, know all sorts of elaborate jumps, and I'm pretty flexible, but apparently, those aren't sports.

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14. I Just Ran

I had just moved to Chicago and was very lonely. This ridiculously hot guy asked me out at the bus stop. Two weeks later, we went on a date. He did T-shirt designs, and I was a pianist, so for our first date, we were going to give each other a lesson in our respective crafts. This was a huge mistake for me My piano was in my apartment, and I lived alone.

I didn’t know this guy, but I was young and dumb—and he was incredibly hot—so I let him in. I should have run. He started going through my things, choked my cat, and knocked my closet door off the track. I was scared and needed to get him out of my apartment in the smoothest way possible. We left to have Thai food. He sat on the same side of the booth as me and burped—with purpose— in my ear.

He also conveniently didn't have any money, and I had to buy his dinner. Then, he let me know he had A RESTRAINING ORDER ON HIM FROM SOME GIRL HE WENT OUT WITH RIGHT BEFORE ME.  As we left and started walking down the street, he flicked a penny at a homeless person, made fun of the sculptures on the street, and screamed at a lady's poodle. It was then I took off, RUNNING away from him.

I ran back home, hoping he couldn't remember where I lived—he did. Hours later, someone let him into my apartment building. I got a knock on my door, looked out the peephole, and saw it was him. I was about to call the authorities, but he ran away when I threatened him with it. He lit up my phone for two weeks after that. I thought I was going to have to move.

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15. This Date Got Bucked Up

I was on a first date, having dinner with a girl I really liked. When leaving, I backed my car into another person's. I was embarrassed, but I handled the situation, exchanged info, etc. While driving her home, I hit a deer. I got out of the car to evaluate the damage and discovered that the deer was still alive and suffering.

There was no animal control to euthanize it, so I did the humane thing and ended its suffering in a quick and respectful manner. We never had a second date.

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16. I Camp Believe What Happened

Years ago, I went out with this girl I met at the summer camp we both worked at. Camp had ended, and I had agreed to drive the hour between our houses and pick her up for a night of teenage romancing. I had spent a number of hours deciding on which restaurant I would take her to, then where to go after, even down to what time I would take her home.

When I arrived to pick her up, I was surprised to see her out on the side of the street rather than in her house, but I paid no mind. I had her hop in, and we were off. Dinner passed without a hitch. After dinner, I suggested that we go to a cafe around the corner for dessert. We ended up splitting a slice of cheesecake, which was how I knew I was doing well with her.

It was starting to get more than a little flirtatious. There was hand-holding and that sort of thing, which set my loins on fire. The entire time, I noticed that she kept ignoring a phone call from someone, but again, I still didn't think to question it. We got up to leave, ready for the passion of the night to begin. She told me about a place on her street where we could park and be alone, which sounded perfect.

I put the pedal to the floor—driving with the heart of a Nascar champion—intent on getting to her street as fast as possible. As we turned on her street, we were greeted by a horrifying sight. There were four cruisers parked outside of her parents’ house. Her response was, "Oh no, I didn't think they would do that". I pulled up to the house in time to have four officers tell me to step outside the car with my hands up.

I learned that the girl was not 17 like she had said, but was actually 15. She had two female parents who were extremely prejudiced towards men in general, so they had disallowed her to see me. She had snuck out to go on a date with me. Her parents had called the authorities, informing them that their daughter had been taken.

So, there I was, an hour away from home, being questioned and trying to hide my quickly dying libido. Eventually, everything was dropped, and I was allowed to go. We did not see each other again.

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17. Our Outing Was A Dead End

When I was in college, I had a blind date with a guy from out of town. I wasn't overly familiar with the area's attractions and relied on him to pick a place—BIG mistake! He offered me pizza for lunch but wanted to eat it somewhere romantic instead of inside the pizza shop. His definition of romantic was a cemetery. So for my very first ever college date, I had pizza in the land of eternal slumber.

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18. Family Matters

I had been trying to date my friend's roommate for a few months and finally got up the courage to ask her out to dinner. Just as we were getting ready to leave her apartment, the phone started ringing. She answered and got this weird look of disgust and concern across her face. She handed me the phone and walked into her bedroom.

As I was bringing the receiver up to my ear, I could hear the sobbing. My brother had been dating my friend, and they had recently broken up. On the other end of the phone was my brother, completely trashed and pining for his girlfriend. After what seemed like an hour, I finally got my brother to tell me where he was.

He was about six miles from his house, calling from a payphone. I tried to get him to call for a ride, but the next thing I knew, he dropped the receiver, and all I could hear were cars driving by. I tried to hang up to call the authorities, but since my brother didn't hang up, I couldn't disconnect from the call. I seriously started to get worried.

In my mind, I was picturing my brother passed out in a parking lot—or worse—getting into his car and attempting to drive home. The rest of the night fell apart as I tried to find my inebriated brother and also get a phone that was 30 miles from my location hung up. We wound up never having dinner, and after that night, she didn't want to talk to anyone from my family.

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19. I Wasn’t Out Of The Woods

I was 17, and summer break had just started. I asked this girl that I was hanging out with—Jenna—if she wanted to be my girlfriend, and she said yes. My new girlfriend asked me if I wanted to hang out with her that night, but I told her that I had already made plans with some friends to go out drinking in a nearby forest.

She asked if she could come, and I thought that would be awesome, so we all ended up meeting up and walking into the forest. Jenna told me that she hadn't had anything significant to eat all day, and me—being an idiot—didn't stop her from drinking on an empty stomach. After about 30 minutes of chugging booze, we all felt pretty tipsy.

I was sitting against a tree with Jenna on my lap. She turned to me, and we started kissing. Immediately after the kiss, she puked all over my pants and blacked out, leaning forward and hitting her head pretty hard on a rock. At that point, she was out cold. Two hours later, she was still unconscious. And then it got even worse. The sun was starting to go down, and the mosquitoes came out.

They were biting everyone like crazy. I called a friend to pick us up, but I had to carry Jenna about a kilometer out of the forest to get to the car. When we got to Jenna's house, her mom came out screaming at me while I was carrying her and apologizing like crazy. The next day, Jenna's mom came over to my house to tell my parents what had happened.

She said, "That's not how you treat a 14-year-old girl". I found out Jenna lied to me about her age! She was also taken to the hospital because her mom thought she was on dope, and her hands were swollen from over 200 mosquito bites. After that, we somehow ended up having a great relationship for about one and a half years.

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20. The Feeling Was Never-Ending

I had been friends with a girl for a while throughout high school and college. We had hung out at school, parents' houses, and parties, so we knew each other well. I eventually convinced her to date me. Being 19 and in suburbia, the Olive Garden was the nicest place I could think to take her. The dinner was uneventful but pleasant.

As we were driving back to a friend's apartment to hang out, we sensed that something was greatly amiss in our stomachs. We just looked at each other nervously as I was driving.  I knew she was thinking the same thing I was—"hurry up and get to the apartment". As we ran through the door, we were greeted by a single, unoccupied bathroom.

We spent the rest of the night taking turns delivering relatively undigested salad, breadsticks, and chicken parmesan to the Clayton County sewers.

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21. Our Date Was A Trainwreck

I went to undergrad about half an hour from New York City. The best way to get in and out of the city was via a train that went to Penn Station, which just so happened to stop running at around 1 AM. I asked a girl out on a date to see a concert in Brooklyn. Everything was going well on the date itself, but the show was running long, so we had almost no chance of making the train.

We still decided to try. We were transferring subways in a rush, flying down the stairs. I must not have noticed the puke on the steps, but it sure noticed me. I wiped out about ten steps from the bottom, sliding on vomit the whole way down. I stood up immediately upon hitting the floor, but there was no salvaging this one or making it look intentional.

My arms, legs, and back were pretty well-coated in vomit. We stopped at a pharmacy to get antibacterial soap, but the puke on my clothing was not really removable. Then, we had to wait in deserted Manhattan for HOURS until the next train back, which was at around 7 AM the next morning.

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22. In The Zone

I tried dating again after a bad breakup. This guy messaged me on OKCupid. We talked and hit it off. He seemed normal and asked me out, so we met up.  The first thing I noticed was his hair. In his pictures, it was long, but in person, it was long, stringy, and greasy. He REALLY needed a haircut or a lesson on how to take care of long hair.

The second thing was how high-pitched his voice was. It was as if he hit puberty, and then in the middle of his voice deepening, it stopped and never finished the job. We got to the restaurant, and he decided to lug his guitar with him. The next thing I noticed was that he was quite a bit shorter than me. Everyone has their preferences, but I prefer taller men, which isn’t so hard because I'm only 5'5” tall.  He was shorter than that.

We clicked, so I thought I could look beyond some of the physical turn-offs. We ate, and he took me to a park. We talked, and I jokingly said, "Oh yeah, I know EVERYTHING about WWII”, which was a hobby of mine. Instead of taking the joke, he berated me into a corner about how HE knew everything about WWII.  I told him to back off, but he HAD to prove he knew more than me when I wasn't being serious to begin with.

After an awkward cheap movie, a couple of days later, I messaged him to friendzone him. Instead, he friend-zoned me, letting me know he was pretty misogynistic. He told me he didn’t believe in being just friends with a girl because he didn’t want to fall in love with them and let them break his heart. Therefore, he couldn’t talk to me anymore. I laughed with relief.

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23. He Got Wigged Out

I had been talking to this guy I met on OKCupid through email for a few months. We decided to meet up. We had one of those epic first dates, the ones that last all day and most of the night. We had drinks and dinner, got caught in a rainstorm, and made out in said rainstorm. After, he wanted to go back to his place to dry off and watch a movie. I was down.

At the time, I was in the middle of growing out my hair, so I had this awesome wig that I would wear. It looked real, and it was securely fastened to my head—or so I thought. One thing led to another, and we were going at it. It was awesome. Midway through, I felt my wig coming loose, but I didn’t want to stop. It eventually came completely off, right as we finished.

It was dark, and he didn't notice. However, I was starting to freak out, so I decided it was best to come clean. I decided that a story about a chemical burn accident during a hair treatment was the best route to take. He was appropriately horrified. At that point, I just decided to grab my wig and leave. I never heard from him again.

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24. Cream Of The Crop

It was the summer before college. I had just graduated from high school, and I met a very shy guy who worked at the ice cream parlor next to the restaurant I worked at. After a few flirtatious meetings, he finally asked me out to a movie. He was a very low talker, so, after an abundance of “excuse me”s and “huh”s, I basically nodded and smiled.

During the movie, he tried to put his arm around me and knocked me in the face with his elbow. To top it all off, we had to leave the movie early because of his 10:00 PM curfew, and I couldn't come to hang out at his house because I wasn't a born-again Christian.

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25. Bad Brew

I met this guy during a party at a friend's house and really hit it off. We agreed to go out. He showed up at my house and rang the doorbell with a six-pack in his hand. He then told me that he needed to use my porch to smoke a bit before we left to go out. Then he asked, “And by the way, what do you want to do anyway"?

I sat on the patio with him while he chain-smoked and suggested that we maybe just grab a drink somewhere. He then pounded back two cans of brew, threw the empty cans on the patio, and walked back inside. At that point, I was flustered, just went with it and followed him back into my house. He then told me that he couldn't drive because he rode a scooter, and I would have to drive.

When we got in my car, he took off his shoes and plastered his dirty feet against the inside of my windshield. I should have turned around right then, but we went to the bar. The bar was nothing special, and after one drink, I said I was ready to go. When I got back to my house, he tried to shove his tongue down my throat.

I did an awkward face turn and got his tongue on my cheek. He then retrieved his four remaining cans from my house and left. We never spoke again.

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26. This Guy Sucked

I went on a first date with a guy I had met online. We were just sitting next to each other, talking, and drinking coffee. We had a lot in common, and everything was going well. Suddenly, he just stopped, looked at me, leaned over, and BIT my neck, not in a soft nibble sort of a way—we're talking full-on vampire chomp.

I jumped away, expecting to need stitches or something based on how much it hurt. Thankfully, he didn't break the skin. If I hadn't dropped my coffee when I jumped away, I probably would've thrown it on him.

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27. I Was Tongue-Tied

I met this guy at my college. We had no classes together, but every time he saw me on campus, he would ask how I was doing and smile at me. Over the course of a few months, we chatted a few times in the library and set up a date to go out for coffee. He didn’t have a car, so I picked him up at a mall that I was unfamiliar with. After I met him, I forgot where I parked.

It took me about 45 minutes to backtrack where I came from, and during that, he was constantly trying to grab my hand, put his hand on my lower back, or rub the back of my neck.  I'm a person who's incredibly uncomfortable with physical contact—even hugs from close friends—so this was extremely awkward for me. We finally found my car, and we headed out for the coffee place.

He placed his hand on my thigh. I tried not to think about it and focus on driving. I chatted mindlessly about interests and stuff, trying to distract myself from the situation. When I let slip that I played World of Warcraft, he made fun of it.  When we finally reached the coffee shop, I found a somewhat-shared interest between us.

He bought me a drink, and we talked about old books. We were getting along better, and for the moment, he stopped touching me—but my nightmare wasn’t over yet. Then, as I was making a point, I held my hand over the center of the table, and he grasped it with both of his hands. He started licking the back of my hand. My voice trailed off, and his eyes met mine. I tugged my hand away and feigned sickness shortly thereafter. After driving him to the college, he kissed me. I never contacted him again.

Teen Phase FactsShutterstock

28. What A Meathead!

I was a vegetarian. One time, I ordered tofu at a restaurant on a first date and the guy asked me if I actually liked tofu. I replied with something along the lines of, "I guess I'm used to it because I'm a vegetarian".  For the next hour, he lectured me about how humans have to eat meat and how I must be pretentious and judgemental.

I didn't argue with him or mention my reasoning for not eating meat, so I had no idea where the rage came from. He was also extremely rude to the waitress. Afterward, he asked me on a second date as if nothing had happened.

Safe Road FactsPikist

29. I Felt Like I Was On A Sinking Ship

I had a train wreck of a first date. It started when I picked her up in my bright pink, two-door 1995 Ford hatchback. It was pouring rain out, and my passenger side window was leaking.  We drove to the ferry terminal for a 25-minute ride to our destination.  The water was rather choppy, and I soon found out she gets motion sickness.

Thirty minutes into the 25-minute ferry ride, I found out that she hadn’t eaten lunch and was super hungry but nauseous as well. We were now 45-minutes into what was supposed to be a 25-minute ferry ride—we were on the wrong ferry! Our dinner reservations were in five minutes. Ten minutes later, we finally arrived at the destination.

We were on the right island but the wrong town.  It was a 35-minute drive to our reservation.  We were unfamiliar with the area, so we got lost. We finally arrived an hour late. My date managed to eat but was past the point of being hungry and her stomach was still heaving from the ferry ride. Then, we missed the last normal ferry back.

We had to waste time for another 45-minutes in order to get on the next ferry.  We both fell asleep on the ferry ride home. I dropped her off and drove another hour back to my place.  For some reason, she agreed to many future dates with me.

Worst Holiday Stories FactsShutterstock

30. Gotta Run!

I went on a date with a guy off of a dating site. Everything was going really well. I was telling the guy how proud of myself I was because I had been training to run a 5k marathon. After two bottles of vino and him continuously trying to kiss me, we were saying goodbye. He leaned over and told me, "You’re going to be so hot when you lose all that weight after running that 5k".

I proceeded to have two delicious donuts on the way home.

Long ConsShutterstock

31. She Left Her Mark

I met this girl through my sister. We talked for a bit, had a non-date lunch, and made plans for dinner and a movie. I drove to pick her up. She was wearing a tattered old dress with a hole on the side and giant sunglasses. I shrugged it off,  we got in my car, and went to the dinner place I had in mind. Dinner went great.

We shared a bottle of red, and the food was really good. We then went to the heart of downtown. This is where the date took an awful turn. I didn't know it, but she was actually pretty sloshed. We were driving around, talking about maybe going to the park or seeing a movie and agreed to go to Navy Pier. When we arrived, there was no parking available, so we decided against it.

Then she said, "Uh, I think I need to pee". So, I drove out of Navy Pier and offered to stop at a bar or something for her to do her business. Very soon afterward, I pulled over in front of a place, but she refused to get out! I was quite confused and she told me that she had to go so bad that if she got out, she might not be able to hold it in and will have to go in the street.

I gave her the benefit of the doubt and found a dark road for her to get out and go in the street. Still, she refused to go. I kept asking why, told her I do it all the time, and said there is nothing to be worried about. She sat for five minutes, refusing. Eventually, she said, "So, I should let you know something. I'm wearing a pad right now and I may have spotted a little".

I didn’t know what that had to do with anything until she got out and ran to a dumpster to do her business. I was in for a surprise. There it was—a puddle on my passenger car seat. I was either an idiot or I didn't want to believe it to be true, but I took my finger and poked the seat and felt warmth on it. The date was over after that. I took her home and never spoke to her again.

Juiciest Gossip factsShutterstock

32.  Date Crasher

I finally got the nerve to ask out this cutie to the movies. I went to pick her up, and she told me I had to meet her parents, which was not a big deal. I was half Spanish, so I knew how important family is for Hispanic people.  When I got there, both her parents started giving us THE TALK—we were both 20 years old. As if that wasn't awkward enough, we had to take her six-year-old brother and 13-year-old sister with us.

To top it all off, I had to pay for everyone.

Embarrassing Moments factsShutterstock

33. Rude Interlude

So I knew this hot girl for a while. She was the kind of girl that whole rooms of guys ogle. One night she called me up and said she was over at the Chili's—which was about a two-minute walk from my house—and she wanted to see me. I agreed, got dressed, and headed over. When I arrived, she was having a brew, so I ordered one too. We moved to a booth and talked.

There were two guys in the booth behind us. She suddenly got up and decided she wanted to join their conversation. Keeping my cool and knowing she was probably testing my endurance, I joined the table. One dude asked if we wanted to go and smoke. While out smoking, this dude was bragging about how many drinks he buys girls and about how much he buys women in general.

I said I had never bought a girl a drink, meaning I never bought a stranger a drink at a bar. We went back inside, sat at our original booth, and within a minute, she leaned in over the table and motioned me towards her. I leaned in, and we started the hottest make-out session across a table. The whole restaurant started cheering loudly and whistling.

She came over to my side, and we continued. We finally paid our bill and left. Then, we decided to go to a university bar and call a cab to pick us up from my house. We headed out to the bar. She then danced and made out with at least five other dudes in front of me. I promptly left with no goodbyes. One test was fine; the rest was just rude. It went from so good to just depressing.

Hate People FactsShutterstock

34. It Was A Total Washout

My worst first date was with a guy I met on He was a physician's assistant. During dinner, he kept playing with his iPhone and showing me grotesque pictures from various medical issues he had seen, which effectively destroyed my appetite. When the bill came, he asked me to pay for our whole dinner because he didn't have any cash.

We had to drive into the city to go to a comedy club, and he insisted that I drive, even though he had a nice new car and my car was really old and a mess. While we were driving, we got caught in the worst rainstorm I have ever been in. While I was trying to keep us from getting in an accident, he was massaging my scalp and neck in the creepiest way possible while telling me he was attracted to me.

He was oblivious to the terrifying storm that we were fully involved in. After the show—which sucked—we left the parking garage, and I made a chilling realization. My debit card was missing.  I had no way of paying the parking attendant. I had no cash, and I was scrambling to find loose change in my vehicle. While I was trying to find the funds to liberate my vehicle from the garage, my date was ignoring me and messing around on his iPhone again.

Finally, a stranger in the car behind me paid for my parking, and we were free. I was on the phone with my bank canceling my card, and at that point, I couldn’t get my date back to his car fast enough. We finally arrived at his car, and just when I thought I was free of his nonsense, out of nowhere, he leaned over to hug me.

I gave him an "Uh, OKAY, this is awkward" pat, and then he started passionately sucking on my neck. As I was pulling back, he grabbed my head, pulled me back to him, and BIT MY NECK! At that point, I’d had enough and shouted, "Well, OK, goodnight then, I've really got to go", and I noped right out of there into the darkness of night.

Comebacks FactsShutterstock

35. Social Media Monster

I adamantly hate social networking. I believe it is a plague on society that we can't go five minutes without checking Facebook, Twitter, etc. I was on a first date at a movie when a few minutes in, she started texting her friend. I asked her what was up, and she said nothing and that she would stop. Another couple of minutes passed, and we were quietly discussing what was going on when she pulled out her phone.

This time, she was updating Facebook. Annoyed at that point, I asked her to please leave the phone alone, at least until the movie was over. She said she was sorry and won’t go on Facebook. Not five minutes passed, and I saw the glow of her phone. She told me that she wasn’t on Facebook but rather on Twitter—that was her excuse. I never bothered to talk to her after that.

Jeff Goldblum factsMax Pixel

36. She Showed Me The Door

I lived in an old apartment. I took a girl out to dinner down the street, so she came to my place first and asked to use the bathroom. The old doorknob broke, and she was locked inside. As she asked what was happening, the terror in her voice was evident. I passed a screwdriver under the door while profusely apologizing. I think she thought I was a psycho.

When we got the doorknob off, I told her I understood if she just wanted to go home. We ended up getting dinner, but it was really awkward and it never went anywhere.

Worst Dates factsShutterstock

37. Party Pooper

I asked a girl out and she suggested we go to her friend's house party. It sounded good to me, so I picked her up and drove to the party. When we got there, we saw the friend, who I sort of knew, as well as a bunch of other people, most of whom I also knew. However, there was one guy there I didn't know—he was my date's boyfriend. They had been going out for a couple of months.

Online Friends FactsShutterstock

38. This Date Grinded To A Halt

I finally agreed to go out with this guy in college. We went for a walk and everything seemed to be going well. We then went into my dorm room and started playing some Nintendo. I think he was mad because I kept beating him, so he pressed pause and started to kiss me. At first, I thought it was alright. Then—I don’t know how—but his teeth were grinding and scratching my lower lip.

I have no idea if it was something he was trying to do on purpose or if he was just THAT bad at kissing. I didn’t want to be mean, so I didn’t say anything to him—bad move on my part.

The next day my lip was bloody and sore near my gums—it was awful. It took about two weeks to heal. We didn’t end up seeing each other after that. I told one of my friends about him and my friend gave him the appropriate nickname—Jaws.

Couples Broke Up FactsWallpaper Flare

39. Oh My Heavens!

I slept with a guy on our first date and he was on top. At first, I thought he was sweating, which was no big deal—I'm a trooper. Then I looked up after a weird muffled sob, and he was crying. As I stared up into his tear-filled eyes—in horror—he stated, "Oh my God, I'm in love with you". At that point, I said loudly, "I have to go. My mom is calling".

I rolled him off of me, grabbed my stuff, and got dressed while walking out of his house. He called after me, sobbing in the doorway. I turned, halfway down the driveway, still pulling my shirt on over my head. He yelled, "Our signs are compatible! WE FIT PERFECTLY TOGETHER, EVEN IN THE HEAVENS".

Weirdest Date FactsShutterstock

40. She Thought She Had It In The Bag

A girl I worked with was in Australia. She was out clubbing one night and met this hot guy. They hit it off and ended up leaving together. Amazing times were had. The next morning, she woke up at the guy's apartment. He was super sweet and even brought her breakfast in bed but then had to leave for work.  He told her she was more than welcome to stick around and shower but told her to lock the door when she left.

Once he left, she felt the need to poop. She took the nastiest post-drinking dump known to mankind. Then, she tried to flush. It wouldn’t go down, and there was no plunger.  So, she decided to doggy-bag it out and throw it away outside. She collected her things—including her bag of poo—and went to write this guy a cute little note.

It said, "Had a great time last night. Here's my contact info". She walked out the door that she had locked behind her, and the door latched. Suddenly, terror set in. She forgot her poop bag, which she had left right next to the note that she had written on the table. Needless to say, he never called.

Embarrassing Moments FactsShutterstock

41. Bloom And Doom

I once went on a date with a man who spent the entire date creepily explaining why his rare orchid collection turned him on. It turned out that he had actually gone on the SAME date with my close friend a few days earlier. We both agreed that he probably wanted to make a skin jacket out of us, and we never returned his calls after that.

Jamaica FactsPixabay

42. Twice In One Night

I once took a girl out for lunch. At her suggestion, we split the bill and planned on going to Taco Bell. I picked her up from her dorm and headed the 100 yards or so to Taco Bell. I wasn't paying much attention, and I ran a red light. We were almost T-boned by a huge truck. We made it to Taco Bell and ate lunch. As we left, I ran THE SAME REDLIGHT AND ALMOST KILLED US AGAIN. I never heard from her again.

Lawyers' defenseShutterstock

43. This Date Got Jacked

My date and I had gone out to eat, then went back to his house afterward to hang out for a bit. As I was leaving, I opened the front door, keys in hand, expecting to see my car directly in front where I had parked it. It was gone. It had been taken from right in front of his house while we were inside. We called the authorities to report it.

I was freaking out so badly that I actually had my date drive me to my ex's house. As soon as I was dropped off, the authorities called me back to let me know that my car had been recovered. My ex had to drive me to some alley in the 'hood to meet up with the officers and my poor car, which had been completely stripped.

Secret Lives Of Rich People FactsShutterstock

44.  Caught In The Act

I met this girl at the university's dining hall. We were both talkative, and after intensely chatting for almost an hour, we exchanged our numbers to meet again. We went to a cafe/pub for the first date. It was going well. After a couple of drinks, I had a short phone call, and then I went to the bathroom. When I got back, I made a disturbing discovery.

I must've forgotten to lock my phone because I saw it in her hands when I got back. She put it down as soon as she saw me. She had gone through all my galleries and Whatsapp.

Dealbreaker DatesShutterstock

45. I Wanted To Ex Out This Date

I had known this girl who I thought was pretty, but she always had boyfriends. I hadn’t seen her in two years, then I saw her in the pub one day.  We caught up briefly and got her number. She suggested we go out for a drink, so we met up. We were having a nice conversation and were enjoying ourselves—she seemed into me.

Her ex-boyfriend had been texting her the whole time, but she ignored it, and we joked about it. Nothing seemed too strange. Then, as we moved on to another pub, he started calling her repeatedly. She eventually answered. Big mistake. He was sloshed, crying, and acting crazy. She told him to leave her alone. We continued enjoying ourselves for a bit while she was constantly being bombarded with his texts.

Then, he started calling her again. This time, he said he was actually OUTSIDE the pub we were at and he could see us. He said all he wanted to do was see her, and then he would go home.  So, she went outside to speak with him. I was just left sitting there contemplating leaving. I got a look at him through the window, and he was an ABSOLUTE mess—it was hard to watch.

She came back inside—nearly in tears—saying how she felt just terrible that she was the reason he felt so bad. I tried to ask her if she was alright and comfort her, but she said she was fine. We ended up just finishing our drinks and calling it a night. I walked her down to the taxi stand, gave her a hug, and saw her off.

Helicopter Parents FactsShutterstock

46. She Was Crying The Blues

I was on a date with this girl. We were walking to the restaurant, and it started to rain. I started humming “Singing In The Rain” and dared her to twirl around a lamp post. This ten-foot cast iron lamp post broke clean off at the base and started to fall over—on her. I did the heroic thing and pushed her out of the way, and grabbed the post trying to keep it from falling.

I didn't realize how heavy the thing would be, and it fell on me, pinning my leg. I managed to get unpinned. We had every officer in the county come to see the commotion, and she left to get the car. While she was gone, the town's lawyer came to meet me while sitting on the curb, icing my leg. I manned up and walked it off.

When she got back, the lawyer looked her straight in the eye and said, "Are you the broad that broke my lamp post" to which she started crying. She couldn't even talk to me for the rest of the date.


47. In Hot Pursuit

I went out on a nice date with a girl. We returned from the bar around midnight. As we turned the corner to her house, she noticed her ex-boyfriend's car parked next to her driveway. We were about 50 feet away, when she asked me to pull over. Suddenly, his headlights turned on and he started driving towards us. She immediately asked me to start driving.

My heart began to race. As soon as we passed his car, he busted a U-turn and engaged us in a frantic pursuit. I slowed down a bit and he cut me off, nearly colliding into my left fender. Then, the dude jumped outside of his SUV and tried to pull my passenger door open just after I locked it. At that point, I was fairly sure that he was one baseball bat away from breaking her out of my vehicle.

I could have gotten out of the car and confronted this madman, but I hadn’t invested enough into this girl to accept that kind of risk on my life. So, as he walked to get something out of his trunk, I hit reverse and headed back to her house. I dropped her off and immediately bailed as this dude continued to chase me out of the neighborhood.

Worst First DatesShutterstock

48. I Wish I Could Skate Away

I was on Facebook with someone I had gone to high school with. I vaguely knew him back then but agreed to a date for when I was home for the holidays. He suggested dinner and ice skating. He picked me up from home and drove to a mall that was pretty far away. I was slightly confused but willing to see where it was going.

He told me to pick any restaurant in the food court, his treat. I thought, “Oookay, I'm a broke college kid too, so whatever”. While we were eating bad food at the food court, he called TWO OTHER GIRLS. He chatted and flirted with them right in front of me. At that point, I was just angry and wanted to go home. I told him that.

He convinced me that we should at least ice skate as he had already bought the tickets. I was pretty far from home and didn't know anyone in the area, so I agreed to go. We went to this ice skating rink. He started telling me of his life ambition to own such a rink, how wonderful it would be if we co-signed for that very ice rink, and how profitable and successful we would be as we were already in love.

At that moment, I REALLY just wanted to go home, but I had no way out. We skated and, luckily, were only there for about 30 minutes. On the drive home, he mentioned that his grandfather lived nearby. It was a special day for him, and he asked if I would mind if we stopped. I said sure. After all, the date couldn’t get any worse—or so I thought.

We pulled into a cemetery. It was about 11 PM, and I was terrified out of my mind. I was frantically texting my parents where I was and what they should do if they didn't hear from me soon. He pulled up to a tombstone and asked if I would like to meet his grandpa. I politely declined. He went out there and sat for a few minutes. He returned to the car, and we drove back to my house.

He tried to go in for the kiss, but I was literally saved by the dog. I rushed inside, locked the door, and told my now-panicked parents the story. Later, when I told him I wasn't interested, he said this verbatim, "Fine, you were weird anyway". My jaw dropped. It was the weirdest date I had ever been on, and nobody believed me except for my parents.

Worst First DatesPexels

49. He Was A Total Dirtbag

We went to a college baseball game. My date parked his car in a dirt lot. It had rained during the game, and when we got back to his car, it was stuck in a mud puddle. He didn’t trust me to drive his car—a Mini Cooper—so he asked if I could push while he drove it out of the mud. The vehicle got unstuck, but not without my lower half getting plastered with mud.

My pants and shoes were ruined. He then asked if I could find another ride home because he didn’t want my muddy self getting in the car. He didn’t even wait around with me until my ride came to pick me up.

Worst First DatesShutterstock

50. Three Was Not A Crowd

There was this cute girl who sat next to me in class. Nearly the whole semester, I talked to her but never asked her out. Then, towards the end of the semester, I finally asked her on a date, and she said yes. So, on the night of the date, I donned my best clothing, wore cologne, and went to pick her up. But, when I got to her apartment, she was with another guy, and they both got in the car.

What she said next left me stunned. The girl told me that it was her husband and they were looking for "a third party to spice things up in their marriage". The date was my interview or something. I decided to go along with it. So, they started asking me really off-the-wall questions. I felt like I was being interviewed for a job making racy films, and I felt dirty.

The couple seemed to be digging my answers, and the girl was cute, so I hung in there. At the end of the dinner, they excused themselves to go to the bathroom and never came back. I guess they weren't digging me after all, so I left and felt like a huge loser. I never told any of my friends about that "date".

Worst First DatesShutterstock


Sources: Reddit,

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