Dating Disasters And Flirting Fails

October 5, 2022 | Kaddy Gibson

Dating Disasters And Flirting Fails

Some people are naturally gifted when it comes to flirting, while others could use a little practice. Yet no matter which group one falls into, the dating game can be hard to play and even the most seasoned charmers are bound to strike out sometime. These Redditors may not have landed a date, but at least their failed attempts at flirting left them with some great stories to tell.

1. Gesundheit!

I was flirting with a girl in a bar, and it seemed to be going well. Then it all went so, so wrong. About a half hour into our conversation, I had one of those very strong sneezes. You know the ones that come out of nowhere and cannot be stopped? I ended up sneezing into my hands…and had a string of goo from my hands to my face when I pulled my hands away. I just walked away.

Dating Disasters And Flirting FailsFlickr, Allan Foster

2. Fake It Till You Make It

I was in line at Subway, and I was friends with the girl who was making the sandwiches that day. She was a cute girl and the guy in front of me was hitting on her as she made his sandwiches. He’d ordered like three or four of them, so he was giving her a hard time for a good 10 minutes while she prepared all of his food.

When he finally paid, he grabbed and kissed her hand as she gave him his change. Then, in the cheesiest voice I've ever heard, he said, "Would you accompany me to the theater, my lady?" I could tell by her face that he was going way too far, so I tapped him on the shoulder and said, "Hey, that's my wife”. He goes, "Prove it".

I just about drew a blank when the girl reached over the counter, grabbed me, and gave me a huge kiss. The dude turned totally red and ran out of the store. Then, she gave me extra cheese for free.

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3. Dance, Dance!

I once saw this guy wait for a girl's friend to go to the toilet, leaving her alone. Then, he started to do this really goofy dance. The guy put his arms out to the side with his elbows bent, then basically bobbed his arms up and down, all the way across the room to the girl. While still arm-bobbing, he said, "Hey…wanna dance?"

She replied, "No". He said, "Okay", then did the arm-bob dance all the way back across the room to where he started in one slick motion.

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4. Schoolyard Games

In sixth grade, I was sitting in class when I noticed the girl I had a massive crush on sticking her tongue out at me in a playful way from across the room. Well, I took this as an invitation to reciprocate. Back and forth, we traded silly faces. That moment may have been the greatest of my entire childhood. But then it was followed by the worst moment.

I felt a tap on my shoulder and spun around to see the guy who loved spending his free time tormenting me. He was tall, good-looking, captain of the basketball team, and bullied me constantly. The guy looked at me like I had just messed with his dog. Apparently, the girl had been trading looks with him, and I was caught in the crossfire. Yeah, that one still stings.

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5. Burrito Boy

I used to work at the mall, and me and my co-workers would go to a certain burrito place for lunch. None of us employees knew the cute Hispanic girls who worked there, but there was one girl that I thought was especially cute. I decided, "By God, I'm going to ask her out!" So, I went to the taqueria and, when she asked me what I wanted on my burrito, I asked for her number.

Since that wasn't a burrito topping, she paused, and then repeated the question. I looked around. There was a line of hungry, impatient people behind me. They were staring, unamused. My momentum was gone. I mumbled something under my breath about, "I've seen you here before”. Misinterpreting what I was asking her, she leaned over, pointed helpfully at one of the possible burrito toppings, and said, "Olives?"

It was at that point that I realized that she did not speak English, beyond the basic vocabulary needed to make a burrito. I relented and ate my lunch in defeat.

Dating Disasters And Flirting FailsFlickr, Alpha

6. Drama Queen

In my first semester of college, I had an uncontrollable crush on a gorgeous, tall, unaffected guy named Alan. He lived on my floor and couldn't be any less into me. I could tell that I had a snowball's chance with him, but the hormones were impossible to ignore. Being very inexperienced, I made one of the worst decisions I possibly could.

I thought that creating drama would inspire him to see me as the cute, vulnerable stereotype I thought all boys wanted. So, I manufactured some reason to need to have a long, emotional talk in the hall. With what I thought was superb timing, I looked up at him with big, teary eyes, paused for two heartbeats and then lunged at him for a kiss.

He called me on it so fast, my head spun. "I knew you were going to do that," he said. "You know I'm not interested in you. What made you think that was going to work?" It was the first time I'd made a pass at a boy since moving to the city from the boonies and it was the first time I'd been rejected.

He did me a favor in a way, though. I never used artifice or stereotypes, and I never created false drama again. But I still wish he had let me kiss him.

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7. Arts And Crafts

I was once smitten with a very attractive bartender. For some strange reason, I thought it would be cute to leave him a paper boat made of toilet paper in the bathroom. Upon my return, I said in my sexiest voice, “I left you something in the bathroom". I wanted to smack my forehead as soon as that sentence escaped my mouth.

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8. Catch!

I was playing Frisbee with a group of people, and I threw it toward this really cute girl. I swear she was looking at me when I threw it...but she turned around as it was still in flight. Someone had called her name, and she turned just in time to have the frisbee hit her right between the eyes. It nearly knocked her out.

It definitely knocked her to the ground. I spent the next two hours apologizing. She got a beautiful set of raccoon eyes from that hit.

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9. Lashing Out

I once had a chick compliment my eyelashes in class. Something along the lines of, "Wow, you have really pretty eyes and long eyelashes". I proceeded to reach up and touch my eyelashes while mumbling something like, "Oh, these things?” In a nervous twitch, my fingers pinched together, and I inadvertently pulled a huge chunk of eyelashes right out of my eyelid. It didn't end there, either. 

She stared in horror as I did the only thing I could think of: I blew a puff of air at the eyelashes and let them go, causing them to sprinkle to the ground like dandelion fluff. That girl never spoke to me again, and I don't blame her.

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10. Do You Believe In Magic?

This story begins three years ago. It was an ordinary day and I needed to use an ATM. I stopped at a shopping center and used one of the ATMs. On my way back to my car, I noticed something glistening in the bright summer sun. It was a small, partially opened bag of glitter. There was a Michael’s nearby, so I assumed it came from there and some poor soul dropped it on the ground.

Naturally, I did what any normal human being in my situation would do. I pocketed the heck out of that glitter. You never know when you’ll need glitter, right? With the glitter in my pocket, I proceeded along with my day. What followed was a typical day. That is, until I wanted to buy myself a book. I made my way to a nearby Barnes and Noble.

I was perusing the books when, out of the corner of my eye, I saw a cute girl. Oh, she was so adorable. Not at all my type, but she had a nice butt and pretty hair. She also happened to work there. Darn it! See, I have this rule: Don’t hit on women while they’re working. Just don’t freakin’ bother people with personal stuff while they’re working.

You’re not special and every other mundane loser out there thinks he’s special when he flirts with the cute waitress. Even so, I hit on her. I asked for her help and made with the joking banter. She was digging it and inevitably asked me for my name. I said, “Orlando”. I followed it up with the stupidest flirting move ever pulled.

I reached into my pocket and pulled out a handful of glitter. I perfectly synchronized throwing this handful into the air with the next words that left my mouth: “Like Orlando Magic”. There was GLITTER EVERYWHERE. Why did I do this? I thought it would be so stupid that it would make her laugh, and perhaps pity or subjective humor would entice her to bed me.

I used to pride myself in pushing the envelope when it comes to courting. This, I learned about a second after the magical thrust of pixie dust, was not one of those situations. Like I said, glitter everywhere. Mostly her face. She screamed, “OWWWW! MY EYE, MY EYE, MY EYE!!” Glitter to the face. Was I a gentleman? No. I walked out.

Not just walked out, but speed walked. You know that thing that 50-year-old women do to stay in shape? That was my escape technique. I acted completely oblivious to this girl and the fact that I just maced her with sparkling iridescent plastic bits. I hadn’t set foot in that Barnes & Noble since, and I’d told this story of utter failure to a select few. Until now.

Today, I went back to this store since I was in the neighborhood and wanted to celebrate an oddly successful meeting by treating myself to a book. I had, for the most part, forgotten all about what happened. This forgetfulness lasted a brief moment, until I entered the store. Then, I had this “Oh, right, I’m a bonehead” moment.

I didn’t turn around and leave because I assumed that after three years, the girl wouldn’t still be working here. I was right about that, but there was one huge problem. It was just my luck that on this day, she just happened to be shopping. I can’t make this stuff up. Not only was she there, but she wasted no time in walking toward me with a determined demeanor.

I wanted to bless her with a little déjà vu and speed walk out of there, but I couldn’t. I was so painstakingly shocked by the fact that this utter nonsense was happening that I couldn’t even move. When she finally arrived and stood right in front of me, in all her 5’4″ glory, she looked up at me with victory in her eyes.

I felt defeated and emasculated. We were face-to-face. She was totally invading my personal space in a way that her eyelashes could probably tickle my chest if she really tried. Then, she said, “Hey Glitter, what the heck?” She didn’t seem mad. She just had this slight look of disapproval, and I frankly expected her to kick me in the balls, at the very least.

I wasn’t sure how to respond to that. I didn’t put much thought into what I said next. I think I defaulted into snarky-Orlando-mode. I looked at her plainly and just said: “Did you at least get the joke?” She literally burst out laughing. Then, she walked away. What a crazy experience.

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11. Gotcha!

I was a cocktail waitress at a club, and this super hot girl was flirting with me. I couldn't believe it! She was smart, interesting, stunningly beautiful...and she actually asked for my number! After I gave it to her, she told me, "My friend thinks you're cute. I'll make sure she calls you”. Yes, it was the ol' bait-and-switch.

She was hooking me up with her friend who was 15 years older than me, way too serious, and not even the slightest bit my type. To make up for it, when the girl called and asked me out on a date, I tried to get out of it. She said she already knew I was free, since I had told her friend, and she wouldn't take "no" for an answer.

So, I brought my two best guy friends along. It actually ended up being a pretty fun night, but there was no way I was going out with that girl again.

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12. Brain Freeze

When I was a raver, me and my friends would all go out and visit this dirty club where pretty much anything went. So, I see this rather hot girl on a staircase, and I was pretty gone by this point. I was like, "Hey, how you doing?" We talked for a minute or so, then I just threw in the question: "So, hey, are you single?"

She goes, "Yeah”. And I just froze up, said nothing, and stood there. After 30 seconds or so, she just goes, "Well, this is awkward", and walks off. It still haunts me to this day!

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13. Luscious Locks

When I was in college, I had long hair for a guy. I'm also a redhead, so it was quite a mane. One brutally cold day, I was wearing a long black overcoat while pumping gas and I heard a voice behind me say, "Hey baby, want to go back to my place to get warm?" I turned around thinking it must have been directed at someone else.

Instead, I saw the most surprised old man I'd ever seen. When he caught sight of my full beard, he jumped like he had just touched a live wire. He stammered, "Oh...God bless you... Ohh...God bless you", as he backpedaled to his pickup truck. The poor guy ran over a curb trying to leave the gas station.

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14. May I Take Your Order?

I'm a waiter at a fine dining restaurant, and I often flirt playfully with female patrons. The other night, I'm waiting on a senior couple and their friend whom they've taken out for her birthday. During the night, I discover that the couple's friend is having a horrible week and seemed sort of lonely. I decide to up my game a little bit. Instead, I made a total fool of myself.

At the end of the night, I'm taking their plates and asking if they'd like desert. The couple orders a slice of cheesecake but their friend declines sort of sadly. Attempting to cheer her up, and probably not in my right mind, I say, "That's too bad, I have a special dessert in mind for you". I wink at her and walk away before the full implications of what I'd just said struck me.

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15. Gal Pals

We were downtown at a bar. Now, I don't normally go out of my way to flirt with or hit on chicks, but there was this one gal...She wasn't "hot" but man, she was exactly my type. And she was obviously the kind of person I really, really wanted to talk to. So, I walk on over and introduce myself to her, feeling more confident than I ever have in similar situations.

She responds warmly but directs my attention to the girl standing next to her. "Sorry, you're really nice and I like you, but this is my girlfriend”.

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16. Lost In Translation

I was at the bar with a co-worker. He saw a cute blonde that he claimed to know, and he said she was German. I was slightly—ok, more than slightly—inebriated and decided that this was the perfect time to go use my German language skills to make an impression. I went over, and mumbled something vaguely resembling, "Wie gehts?" Oh boy, did this backfire on me.

The girl didn’t understand me and asked me to repeat myself. I did so two more times, at which point she asks me, "What the heck are you saying?” Quite aware now that there was no doubt that this girl was American like me, I quickly explained what my jerk friend had told me. After apologizing, I quickly walked away in shame.

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17. Two Left Feet

When I was 18 or 19, there was this cute hippie girl who I had an absolutely massive crush on. We had been talking for a little while, and things were looking positive. One day, myself and a group of folks went to meet up with her and her group of people in a park. When we got there, and everybody started greeting one another.

The girl and I kind of drifted together to do a little greet-with-a-hug kind of thing. Keep in mind, this was a hippie girl. Wearing Birkenstocks. I stepped in to give her a hug, and then I kick her big toenail clean off. Completely off. So, yeah, she was bleeding and in a lot of pain. I wasn’t sure what to do. 15 or 20 people were there gasping and commenting. It was pretty darn awkward.

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18. Just A Taste

One night, during my freshman year of college, my girlfriends and I decided to get dressed up and go out to some frat party. Foolproof idea. Several hours later, properly sloshed and dressed up, we made it to the party and promptly hit the dance floor. This guy came and started dancing with me using some hip-thrusting bro motion. Whatever they do these days. Only, I had no idea what I was in for. 

30 seconds later, he BITES MY NECK out of nowhere. Just straight up grinding and gnawing at my neck. So, naturally, I elbowed him as hard as I could in his stomach and walked away calmly. He actually hunted me down and acted all injured that I was mad. Oh, Long Islanders.

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19. Center Of Attention

When I was 13, and in my first year of secondary school, I hit upon a BRILLIANT plan: I was going to throw a party at my house to celebrate the end of school. Not being popular at all, I was amazed when HALF THE TOWN ended up there. Even the one guy who had a reputation for being cool, well-dressed, and super attractive showed up.

I must have seen too many John Hughes movies because I was certain he would fall for me that night. So, everyone arrived, and the party was going brilliantly. Full of dumb confidence, I strolled over to Cool Guy and asked him to dance. And he told that me he can't because he was there with his girlfriend, who was standing there laughing. Oh, but it got more embarrassing.

Then EVERYONE else started laughing at me, too. In one quick moment, I had created a social and romantic disaster. I was so shocked, and the rest of the party was ruined for me. I let folks have the run of the house while I went and slept off the embarrassment. Luckily, these were more innocent times, so nothing was broken or stolen.

But I still get a shiver of horror when I think of that night.

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20. Balancing Act

I was at one of my high school soccer games, and I had been subbed out. While I was on the sideline, I started messing around with a soccer ball and chatting it up with our cute trainer. She was way out of my league, but she seemed interested anyway. So, I absent-mindedly started standing on the ball, while still chatting.

I ended up standing on it for a good two minutes…until I stepped off it and tried to stand back on it. My feet ended up over my head and I landed squarely on my back. The trainer just gave me an embarrassed look and walked away without saying another word in the middle of the conversation we were having. I never spoke to her again.

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21. Riveting Conversation

I had just moved to DC from Indiana and was completely oblivious to the very distinct differences in culture between the Midwest and the East Coast. So, I was on the metro one day, and this really cute girl sat down next to me. I sat there for a couple of stops, trying to come up with my best line. I thought to myself, “What could possibly go wrong flirting with a random girl on the metro?” How, it went wrong all right.

Having conceived the best pickup line ever, I turned to her and said, "So, what's more awkward: sitting next to someone you don't know and never talking to them, or trying to start a conversation with someone you've never met before?" Without missing a beat, and barely even acknowledging me, she replied, "Trying to talk to someone". I stayed quiet the rest of the way.

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22. Oblivious

I was working a cash register in a gas station and this beautiful blonde girl walked in. While she was paying for her stuff, she started complimenting me. A lot. It was like a non-stop barrage of compliments. I was completely baffled. I had never had anybody compliment me on anything and I was unprepared for so many of them.

I think she could see that I was confused, so she said, "I'm flirting with you". I didn't know how to respond. All I could say was, "Oh". Without another word, she took her things and left.

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23. Single And Ready To Mingle

I was out one-night-stand shopping when I saw this guy who I had been flirting with for months at the bar. I thought he was so attractive. He came into my work and just chatted me up all the time, and I was always under the impression he would want to hook up sometime. Well, when I finally got up the courage to ask if he had a girlfriend, he said, "Nope".

He didn't seem to get that I was making a move, so I was like, "Well, that's cool. I’m not seeing anyone either”. His response made my jaw drop. He said, "Well, it looks like it is going to stay that way”. It took a while for the sting of that one to wear off.

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24. French Kiss

I took this girl out on a date when I was in high school. I think I liked her more than she liked me, and I just couldn't believe she was on a date with me. Anyway, the movie we watched was an old one and it was a weekday afternoon, so we were the only ones there. We ran around the place, jumping over seats and trying to play tag.

Finally, I ran over to her, and she stopped running and just turned around. I grabbed her and I knew that was the moment I was probably going to have my first kiss. So, I held her close, closed my eyes, and leaned in for the kiss. I was clueless to this kissing thing—there was no communication involved and it was like going in for a handshake or fist bump.

So, I leaned in with my mouth closed and puckered. Her lips were partly open. We connected and I quickly moved my head back. The first words out of my mouth were, "Don't use your tongue". She said, “I wasn't going to..." Yeah, we broke up shortly after that.

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25. What’s My Name?

I went to a local diner to meet some friends one night. This guy started hitting on me and simply would not quit. He introduced himself as Brian and invited himself to eat with us. My friends were laughing uproariously while I glared at them. I kept telling him I had a boyfriend. Finally, he says, "I can make you forget your boyfriend's name". But I had the perfect reply.

I responded, "But my boyfriend's name is Brian". The look on his face was priceless, and my friends burst out laughing again.

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26. Natural Attraction

During a biology final, the cute girl from my lab group found me and sat in the seat next to mine. She made me nervous, but I knew I could make her laugh, and she was the best thing about freshman bio lab. We talked about what we might do after the semester was through, and I was trying to find an excuse to mention something that might involve us.

She mentioned a band she liked. I said, "Have you ever gone to see them?" She perked up and said, "So many times! One summer, my friends and I followed them around everywhere, we even snuck backstage a few times! It was like we were—" I interrupted her and said, "Freaks?" She scowled, "...I was going to say, ‘like roadies...’”

I don't know how the word "freaks" came out. I rarely said that word. I hated that word. After it came out, it was hanging there like a taut noose around my neck. The final began. She finished before I did, and I never saw her again.

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27. Trainspotter

This happened a few years ago. I saw two girls on a subway platform. The one facing me was super cute, so I sauntered over and started to strike up a conversation. But I had made the worst mistake of my life. Turns out the other girl was my recent ex. She had changed her hair pretty drastically, so I didn't recognize her from behind. Things got awkward real quick.

Even though I slunk away pretty much immediately, there wasn't really anywhere to go. And the train took forever to arrive, of course.

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28. Fine Dining

I was on a first date with someone I was interested in. We went to a Japanese restaurant, and I ordered a sushi roll. I figured the restaurant would have normal-sized sushi, just small enough to fit the piece in your mouth and still be able to chew it. So, when I got the sushi, I immediately just popped one in my mouth.

Force of habit, you know? Usually, if you don't eat the piece all at once it falls apart. It was only when I tried to chew the piece that I realized it was absolutely huge. I might as well have tried to swallow a car tire. So, with the cute guy watching me, I had bits of rice, raw fish, and drool falling out of my mouth while I attempted to just get the sushi down my throat.

After I swallowed, I just kind of sat there thinking, “Oh, God that was so disgusting. How could he ever watch that and not be disgusted? He's just gonna leave me here, right now”. We just celebrated our three-month anniversary today.

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29. Hide And Seek

A few years ago, I had just broken up with a girl that I'd been dating for two years. I was in my heavy drinking phase, so I was having 10+ drinks when I went out. One night, I met up with an old co-worker and friend. She mentioned that she was in a crumbling long-distance relationship. So, we went out with a group to a club, and we were dancing.

For most of the night, my friend was flirting with me. At one point late in the night, she made a direct pass at me. I was freaked out because I thought she was in a relationship, even though it turns out she was on the precipice of ending it. In my drunken stupor, I could think of only one thing to say. The most disgusting sentence left my mouth. "OH, MY GOD, I HAVE TO POOP SO BAD!"

I then ran off into the men's room to hide for a few minutes. Fast-forward a few years later and we're now engaged. I guess all’s well that ends well.

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30. Shelve It

I had been working with a girl at a supermarket for nearly three years. We were pretty good friends. We hung out together sometimes, got plastered together sometimes, but there was nothing very serious. Certainly, nothing that could have been misconstrued as a date. Even so, I was smitten with her. It was my final year of high school, and I had no date for the formal.

One day, while we were both restocking the shelves, I asked, "Hey, Amanda, it's the formal soon. Would you be my summer girl?" She pretty much did a spit-take: “PFFFFFFFFFFFFFFFFFF, no." Then, she went back to stacking shelves. We never spoke of that again.

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31. A Trip Down Under

I had been attempting to flirt with a gorgeous girl in the library around exam time in my second year of university. Every day, for about two weeks, I had tried to think of something to say to her or some way to get myself noticed. One afternoon, I opened the door at the top of the stairs and there she was on the other side.

I held the door for her as she walked through. She looked me straight in the eyes and said "thanks" in the most adorable way. It was the perfect moment to strike with charm and wit, but my brain malfunctioned. I took a massive servant-style bow and said in a thick, loud Australian accent, "NOOO WORRRRRIES, MAAAATE!". Regrettable.

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32. Pen Pal

I was at an outdoor café when I saw a hot girl nearby. I knew I had to do something. So, I wrote her a note saying that she was gorgeous and asking her if she was single. It was a little clumsy, I know, but it seemed better than doing nothing. I asked the waiter to give her the note. Turns out the waiter was her boyfriend.

He was actually a good sport, and we had a laugh about the whole thing. He gave the note to her. Of course, she said that she wasn't interested. But hey, if you don't try anything, you’ll never get anywhere.

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33. Business As Usual

I was in Sarajevo with some friends. We'd found out about a pretty big club with an awesome sound system and ravey atmosphere. There was this group of girls dancing next to our bunch of guys and, as happens, one or two were glancing over. So, with my Dutch courage, I figure, “What the heck?” I walked straight over to the best-looking girl in that group.

My plan was to charm our two groups together and be heralded as a hero for years to come. It turned into an utter disaster. But instead, I tapped the girl on the shoulder and realized pretty quick that she didn't speak any English. So, in an attempt to get my smooth opener of “Hi” understood, I waved at her. Pretty much in her face. She just stood there looking confused.

Suddenly aware of my friends' glares on my back, I panicked and shook her hand. Not in a cheesy “enchanté” way, but in a cold-yet-efficient business-like manner. After three firm handshakes, I turned around and walked away thoroughly confused as to what had just happened.

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34. Coffee Time

One time, I was having a day to myself with a mocha from Starbucks. I had just gone to the store and looked at a pair of corduroys. I don’t usually like corduroys, but they looked really good. So, I said, “screw it”, and bought them anyway. I still wasn’t sure about them, though. After I got the pants, I went to Borders.

I was looking at the books on hypnosis, and I picked a few of them up. There were also a few books on natural language processing, which is basically getting really good at reading people, persuasion, etc. I was sitting there when this insanely cute girl sat across from me. After 15 minutes of working up the courage to talk to her, I walked over.

The first thing that popped into my head was to get her thoughts on corduroy pants. It seemed like a good way to open the conversation and was a legit question in my mind at the time. I approached her and she looked up from her book. I went to speak…but a loogie came up in my throat from the freakin’ chocolate mocha coffee.

My words sort of jumbled up and my face instantly got really red. I started fumbling through my words in the most agonizingly horrible way because I was embarrassed and worried about talking through all the mucus. It basically came out as: “Hey, whughhh…what… about...corduroy…pants? Uh…yeah”.

She looked at me for a solid five seconds, inquisitively, before completely avoiding my question and changing the subject. She replied, "Hey, there. So…What books are you reading?" I looked down and I had a stack of books next to me titled How to Influence People, How to be the Best Conversationalist on Your Block, etc., etc.

She looked at them and giggled. Then, before she got up and left, she winked and said, "Keep reading".

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35. Pajama Party

I was 17 and had managed to get turned loose in Milan all by myself at a youth hostel. Met this SMOKIN' hot Brazilian girl my age. We flirted, went to a club, and started drinking. Well, after the second drink of the night, we decided to get shots. In this particular bar, a "shot” was more like a triple shot.

The girl looked right at me and DOWNED the darn thing. I was just sipping on it because I knew my inexperienced digestive tract would simply reject that unusually large quantity of rotted agave. But she started to challenge me: "You a coward? Just drink it!" I, of course, complied. I downed the shot, then promptly barfed all over the bar. But then I made it so much worse.

I panicked and ran into the crowd so the bouncers couldn’t throw me out. The girl followed me, and we started making out HARD after I had just vomited. Later that night, we got back to the hostel, and I went to start changing into pajamas. The girl followed me to my locker and started GRINDING into me and making out.

I stupidly continued making out with her, not making the next move. She got frustrated and just left to go up to her room. As she left, I managed a weak, "Wanna borrow some pajamas?" I don't think she heard me. About two years later, I was sitting retelling this story to some friends. That was when I finally realized what she wanted from me.

Dating Disasters And Flirting FailsPexels

36. Copycat

I met this friend-of-a-friend-of-mine at a bar last summer. She was so beautiful that my brain instinctually went into instant “behave like an idiot mode”, as it tends to do. When I got around to introducing myself, she said, “Hi, I'm Laura”, before making a weird and quirky arm movement. I could only identify it as some sort of a parody of a hip-hop street greeting, if you know what I mean.

Since I was so stunned by Laura’s beauty, and I could not come up with anything else, I thought, "I'd better play along". So, I copied the wacky arm movement hoping that she'd appreciate my acknowledgement of her quirkiness. A frown appeared on her face, and without saying anything she just stood up and left the table.

My friend looked awfully embarrassed. The entire table looked embarrassed and basically ignored me the rest of the night. I didn't see Laura for an hour or so. The next time my eyes caught a glimpse of her, I understood what I had just done. As she was standing at the bar with another group of friends, I saw her doing the exact same arm movement, continuously.

It was then and there I learned from my friend that Laura is spastic. Surprisingly, we never got married.

Dating Disasters And Flirting FailsPexels

37. Unforgettable

My friend works as a cashier at a grocery store. He's not the type to be easily wowed by the ladies, but when he is, he's floored. He is usually very smooth of tongue but becomes wordless when he's actually interested. Anyway, a few weeks ago, this chick came to his counter, and he was like, "Oh, my God, she is super hot”.

So, he started talking with her. After a while, he asked for her number. That's when he realized the awful truth. She replied, "Oh…Well, uh, I gave it to you a few weeks ago". The remainder of the transaction was silent and awkward. She waved to him abashedly while leaving. He kicked himself pretty hard over that one.

Dating Disasters And Flirting FailsPexels

38. Technical Difficulties

I'd been flirting with this girl off and on for about a week. One random day, I decided to make a bit ol' pot of chili for lunch and dinner. After dinner and my third helping of chili, I got a call from the girl saying she needed help with her printer. So, I went over to help with her printer and afterward we were just sitting and talking.

During this time, I was holding back a potentially massive chili dump. She eventually invited me to spend the night, which gave me three options: I could have dropped a deuce at her place, I could try to hold it, or I could respectfully bow out and try again next time. The first option would probably have ended with her bathroom ruined for a couple hours.

Maybe I could get some play after option one, but I knew that was very unlikely. With the second option, I’d probably end up pooping myself, resulting in me never getting any play for the rest of my college life. So, I ended up playing it safe and picked the third option. Guess, I should have dropped that deuce because the girl never really spoke to me ever again.

The sad thing is that we would have had a blast together. But at least I didn't poop myself.

Dating Disasters And Flirting FailsPexels

39. Just Do It

I'm really bad at making a move on certain people. Namely people I respect more than average. It’s weird. Anyway, one time I was hanging out with this girl in my room, and I wasn't getting the vibe from her...but I also kind of was. I was very confused. So, I thought to myself, "Okay, let's get this out of the way", and I just went for it.

I leaned in to kiss her and she put her arms up and said, "Whoa, whoa, what? Sorry, no". Turns out, I had just done the worst possible action. It turned out that when I was thinking to myself that I wanted to get this out of the way, I didn't really think it. I said it out loud and very audibly.

Apparently, trying to make a move and referring to it as some sort of bothersome chore is a bad strategy.

Dating Disasters And Flirting FailsPexels

40. Liquid Courage

In college, I used to go to this bar every Wednesday with my friends and drink way too much. Well, this one Wednesday I was there plastered out of my mind and there was this gorgeous girl at the bar. She was so gorgeous, in fact, that I would never have hit on her unless I was as tipsy as I was at the time. I walked over.

I said, "Hi, can I buy you a drink?" She looked at me with disgust and said, "Jon, every Wednesday you hit on me and every Wednesday I tell you to go away". Well, I was so plastered that I replied, "So, do you want to go for a walk or something?" She just walked away. The worst part is that I don't remember what she looks like, so I may hit on her again.

Dating Disasters And Flirting FailsPexels

41. Tongue-Tied

I once told a girl I had a crush on that I liked her brother. By accident. See, what I meant to say was, "I like your bra". But as I was saying that, I suddenly thought to myself, "Oh, I probably shouldn't say that since it would give away that I've been looking through the folds on the front of her button-up shirt to the bra underneath".

So, “bra” and “oh” got mixed to form “bro”. And I said ,"I like your bro". She looked at me funny and said, "I don't have a brother. You must be thinking of my cousin. He's not into guys, though". I walked away, wondering what the heck had happened.

Dating Disasters And Flirting FailsPexels

42. A Burning Desire

In high school, when I was 14 or 15, I rode the bus with a girl who had blossomed early. She was from a different group than me, and we did some occasional flirting but chances for actual interaction were rare. One day, while we were standing around waiting for the buses to arrive, I noticed that her jean shorts were cut very short. I made a very bad decision. 

For some reason, I thought it would be hilarious to light the fringe of her shorts on fire with my lighter. Keep in mind I was guided only by hormones. I thought it would be like a sock fire or something like a little "woosh!" and then go out. So, when the girl’s back was turned, I took my lighter and lit right under her butt.

Of course, the frayed cotton of the shorts immediately lit right up and showed no indication of going out. Immediately, I recognized that I had made a major error. I started slapping at her upper thigh and butt in an attempt to get it out. It did go out, but of course I had run up behind her and, from her perspective, had begun roughly grabbing at her.

Attempting to smooth it over with, "I was trying to put out the fire that I had set upon you", didn't go over any better. Needless to say, I’m lucky I wasn’t locked up for the situation. The girl just decided to avoid me—and rightly so—from then on out.

Dating Disasters And Flirting FailsPexels

43. Dressed To Impress

I'm more about mixed signals. One girl told me she liked the suit I was wearing and that led me to talk about how cheaply I bought it for.

Dating Disasters And Flirting FailsPexels

44. An Acquired Taste

Once, I propositioned a fine young lass by informing her that my testicles smelled like the finest of handcrafted cheeses. The lady was not, in fact, wooed.

Dating Disasters And Flirting FailsPexels

45. Smoke Break

I asked her if she wanted to step out for a cigarette so we could talk more in private. It was actually the most embarrassing thing I could have done. She told me her mother had lung cancer. I apologized and walked away.

Dating Disasters And Flirting FailsUnsplash, whoislimos

46. Misunderstood

My failed flirting attempts usually involve girls not recognizing sarcasm. My favorite of these instances happened when, in response to a girl mentioning she was taking a class on race relations, I said "That's interesting, I'm actually racist myself". Her eyes got really big, and she got real quiet: "Are you serious?"

Dating Disasters And Flirting FailsUnsplash, Etty Fidele

47. Life Lessons

Back in my first year of college, I took a girl I'd had a huge crush on to see a movie. Near the closing credits, I leaned in to kiss her. What happened next mortified me to m core. She leapt out of the seat and screamed, "NO!!!!" at the top of her lungs in the middle of the theatre. Driving her home was pretty awkward, but after that I had a lot more confidence asking girls out.

I figured, "What's the worst rejection that could happen? Scream in terror in front of more than a hundred people? Been there, done that". Dating and flirting got a lot easier after that.

Dating Disasters And Flirting FailsPexels

48. The Waiting Game

My buddy had been talking about this girl he had been hanging with for a while. He had been taking her out to various venues and just spending time with her but had not worked up the courage to kiss her. He finally decided to introduce me to her and told me to meet him at this bar we liked to go to. I walked into the bar, and my buddy was nowhere in sight.

So, I texted him and he says he is running a little late, and that he will show up in another hour or so. I start ordering drinks and at the bar I notice this girl who is not bad looking. She seems as frustrated as I am. We got to talking about how unreliable people can be, introduced ourselves, and I took her to play a game of pool. You can guess the horrible thing that happened after that.

We were flirting pretty hard throughout this game, with her "accidentally" brushing up against me and whatnot. Eventually, I made a bet with her on the next shot: if I made it, she’d owe me a kiss. I sink the shot and made out with her for a few minutes...only to find out that she was the girl my buddy had been seeing.

We didn’t inform him about what happened for a few months, but they’ve been together since that night.

Dating Disasters And Flirting FailsPexels

49. Burn, Baby, Burn

This happened in San Diego, during my first visit to Southern California. I'm from Western New York and burn like you wouldn't believe in the sun. I walked all over the place without sunscreen. My face was swollen and peeling, but I forgot about it because I was really tipsy. We were out at the bars and I was talking to this cute girl, thinking I was being devastatingly charming.

Suddenly, she stopped me and said, "I don't mean to stop you, and you seem like a really nice guy, but do you need to go to the hospital? Your face is really swollen". Devastating. Part two happened when I was out on the patio a couple hours later. I found a really attractive girl who was inebriated enough to not care about my hugely swollen and cracked face.

That should have been my first clue. Sadly, she was so tipsy that she threw up right after she asked me to come home with her, and security kicked her out. I probably dodged a bullet there, but that night was so robustly full of failure.

Dating Disasters And Flirting FailsFlickr, Amy Halligan

50. Flying Solo

I was at a bar with some girlfriends of mine when a very handsome guy came up to me. He spoke to me for 10 seconds and then shoved his shy and unfortunate-looking friend in front of me. In this moment, it was clear to me that the handsome dude was trying really hard to be a wingman for his awkward friend and get him acclimated to talking to girls.

This, for whatever reason touched my heart, so I set about having a polite and friendly conversation with Awkward Dude. Awkward Dude proceeded to chat me up and I pretended to not see the thumbs up from Handsome Friend. Awkward Dude seemed to be a nice guy, just painfully shy. He asked me where I was from about three times after I'd already told him.

Each time was followed by high-pitched laughter and, "I'm sorry, I already asked you that…ummm…". It was endearing. The guy was clearly on the verge of a panic attack from just speaking with me, but I was being very careful to give him positive reinforcement to build his confidence. But it all unraveled in an instant.

That’s when my catty friend came up to me. She looked at the guy, grabbed my arm and said, "UGH, okay, I'm saving you!" She tried to pull me away, but I stopped her and said, "No, I'm having fun. I'll be over in a minute". She literally POINTED AND LAUGHED at the guy.

Then, she made some mean joke about my "charity work". The look on the dude's face still makes me wince when I think about it. He was totally crushed. It was like every doubt or criticism he had about himself was validated in that moment. The guy just walked away from me as fast as he could, totally humiliated.

I know it’s hard to get over something like that, but I hope Awkward Dude didn’t give up on dating. He really did seem like a sweet guy.

Dating Disasters And Flirting FailsPexels

Sources: Reddit,

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