Flirting with someone can be embarrassing if you don't know how to approach them respectfully and these stories are proof.
Flirting is not as easy as it sounds. One requires a certain level of confidence and charm to respectfully approach a person and try to woo them with their words or actions. Well, if you are not flirting the right way then you are obviously doing it dangerously wrong. Everybody might have had at least one experience in their life where they have attempted to flirt with their crush or tried to approach that cute woman or guy at a bar but ended up completely jeopardizing the situation with the wrong choice of words or action. So, u/Veetojek asked the Reddit community to share their stories involving the worst and cringeworthy attempts at flirting they have even witnessed or done themselves. Hundreds of comments poured in and here are some of the downright disastrous flirting fails that you've ever heard of.
My friend in college started hanging out with “pick-up artists” and decided to demonstrate his prowess to us on the quad. His strategy was to approach a girl and ask what she thought he should make for dinner that night. He then very much not confidently approached a girl who was clearly in a hurry and, staring at the ground, delivered the line. The girl glared at him and, with great annoyance, said “I have no idea! Spaghetti, or something?” And my buddy, still staring at the ground, said “Oh-oh-ok. Uh, thanks” and shuffled away. He also “learned” from this group that you’re supposed to touch a girl’s arm every time she laughs to condition her to associate your touch with a release of dopamine or endorphins or something. So I witnessed this several times as well, never done with any subtlety or charisma. -u/Dr_broadnoodle
It was me. In sixth grade, I wrote a girl’s name on a rock and threw it at her during recess. Apparently, they don’t like that. -u/Neon_Eyeballs. It wasn't your fault that rock was thrown at a girl you like, it's probably in all our DNA stemming from the caveman days when they couldn't communicate with speech, they most likely hurled rocks at cavewomen to show interest. -u/elimin8a. Throw chocolate, from a safe distance. -u/Mc60123e.
Guy on a trip saw a new girl in our group that he found cute. Decided to take the insult-as-a-form-of-flirting path and told her she had really hairy arms for a girl. Mind you, she had incredibly fair skin, so her hair stood out more than usual. She, having too nice of a personality to say anything, laughed it off, covered her arm in a real smooth manner and went on with whatever conversation was happening. My guy thought it worked because it "made her laugh" and you know you've got the green light when she laughs at your jokes. The next day he goes up to her during breakfast thinking he locked it up and exclaims, "Oh my god your arms are so hairy that it's gonna make me sick!" She doesn't laugh this time, runs back to her room and changes into a long-sleeve shirt. She proceeded to wear long-sleeve shirts or sweaters for the remainder of the trip...in the middle of July. They didn't have a single interaction for the remaining 4 days. -u/TYRONEmonies
On a walk with my dog, hot sweaty and not in the best clothes. This man drove behind me following me for a few minutes and I looked and said "Can I help you?" He said let’s go on a date! Hop in! I said no thanks and he revved his engine, asked if I was sure then sped off. I was legit scared. -u/Allieora. In Brazil, before I graduated from high school, all of the boys who wanted to pick up girls bought motorcycles, they didn't need them and they didn't work or live too far. -u/Veetojek. My wife was walking our dogs by herself and a car pulled up to her and stopped. She was quite concerned. The guy rolled down his window and said "Your dogs are gorgeous. Are you interested in studding them?" -u/Seaniard.
I was drunk at a party talking to a cute girl. She took her glasses off. I thought this would be a good time for a genuine compliment. What my mouth said, "I like your face better with your glasses on." She just laughed. Pretty sure what I was trying to say was "I like your glasses and you have a pretty face." I just combined them. -u/HooterEnthusiast. Years ago I was working at a small shop and this girl came in on vacation once a year and one of the times she came in, I overheard her talking about how she was planning on cheating on her boyfriend because she was bored of him. Immediately, all respect for her is gone and I’m grossed out. She seemed excited to talk to me though, so, she was going on about something I can’t even remember anymore and for some reason my absolute pile of poop brain combined the words “cool” and “sweet” so what came out of my mouth was “oh, qu*ef” and she just stopped and looked at me funny for a second in silence before just leaving. -u/Suuukah
Reminds me of the first thing I said to the first woman I met through an online dating app. I just froze, because she was even hotter than her photo. She took it as if something was wrong and asked something to that effect. I said, "You're skinnier." We still ended up dating, but man, I had some bugs to work out in my game. And while I never fell into the pickup artist stuff, I did decide to take "women like confident men who challenge them" and, for some reason, I have no excuse for, decided to demonstrate this by getting into an argument with her friend about whether it was Lionel or Lion-O from the Thundercats. u/Odd_Counter_7943
When I was in 3rd grade, I had a crush on my babysitter. I decided to impress her by demonstrating my acrobatic prowess. I sprung from the side of a spiral slide and grabbed the monkey bars without touching the ground. Unfortunately, my hands slipped, I flipped through the air and shattered my wrist in two places upon landing. My first thought was, "Don't cry, be tough." Then I saw my wrist, it looked like a sine wave. I immediately started crying. u/ANerdCalledMike
I think I have seen worse but I will share my attempt at flirting with my best friend's roommate. It was the first or second time we met, we were drinking at their apartment and we were hitting it off pretty well. Later that night, we wanted to move on to another location to meet some of her friends. On our way there, we came along a guy who was walking around selling roses. She said they were looking nice or something, so I quietly went back to that guy and bought one for her. She had a big smile on her face when I gave it to her and said that it was the first time someone had given her a rose. So far so good. Unfortunately, I am awkward and didn't think that far ahead, so I completely derped out and said something stupid along the lines of "there is a first time for everything" as my mind went blank. I don't remember how she reacted but the tiny bit of courage I had mustered up to do this was gone and it never went any further. u/Captain4verage
When I was working at a gas station, I had a dude just walk up to the register and just go "Hey you have a boyfriend?" Of course, he didn’t take "I’m not interested" for an answer after. My assistant manager had to shove him out the door to get him to leave. Sadly, he wasn’t the only one in the four years I worked there. Had one guy hitting on me asking what I was doing later. I wasn’t acknowledging the question, making him mad. My coworker on the other register though was like "Sir, knock it off." Then all of a sudden a kid around 10-12 years old came running up going "Daddy, daddy mommy said hurry up!’ He couldn’t run out faster after. My coworkers and I had a laugh at him after. u/SilverSoulFox.
A new girl comes in and it’s literally her first day. Beautiful 18-year-old girl. Went to lunch with her and this other dude. He asked me to let him talk to her because he knew every guy was waiting for the chance to try and make a move. I was shy and insecure so I wasn’t going to try anyway. So, he sits down next to her and the conversation is casual for like two minutes, exchanging names, ages, where they’re from, etc. And then this man stands up and walks over to her gets on one knee and proclaims his love for her, love at first sight basically. He said he didn’t have the money for a ring yet but wanted to let her know his intentions now. Man went from zero to a million in mere minutes. He was an immigrant from Iraq I believe so maybe it’s a cultural difference idk. But I talked to the girl about it a couple of days later and she thought it was super aggressive and felt uncomfortable with the entire scenario. Bro never stood a chance with that attempt. u/Jac1596