What was your WORST attempt at flirting?

Question

My all time favorite was at 6am, I went to pick up some donuts, and saw this hot guy exiting his car, and I'm looking over trying to catch his eye and right when I do, not looking where I'm going, I tripped over a piece of wood in between the concrete in the sidewalk that had come loose. In the dead quiet of the morning, this wood piece makes this intensely loud thwacking sound as it reverberates back and forth from the concrete. Next thing I know, I'm going arms, donuts, and head first into a brick pillar. Luckily I was able to stop right before giving myself a concussion. I immediately start laughing because I do that when I'm embarrassed and I look up and this guy is giving me the, "you're a total weirdo" face. It. did. not. go. well.

TommyMountainFigure · Accepted Answer

Worst huh? Unfortunately, I have way too many instances to choose from. Here's a couple.

1) I had this thing for my best friend's Sister when I was 15. She was 22. She made a party and allowed her brother to invite a few of his friends. Of course, there I am telling her I think she is the most gorgeous woman I have ever seen, and her boyfriend was standing right behind me with all his friends laughing at my poor attempts at getting a date with her! I was mortified, but at least they both saw the funny side of it and I never got beaten up!

2) I was on a motorbike when I was 19, and as I was riding along in traffic I saw this girl sitting in the passenger seat looking back at me from the car in front, so I decided to blow her a kiss. As I did so, her boyfriend who I didn't know happened to be driving the car slammed his brakes on, and I went crashing in to him. He got out to a) assess any damage although there wasn't any. just my wheel buckled a bit. and b) to punch my lights out. I managed to talk my way out of that one by saying "I stretched my arm out because of a bit of cramp and wasn't blowing anyone a kiss'

GuyAnswersGirls123 · Accepted Answer

One time I dated a nurse but before we started dating and just in the flirty stage, she told me she was a nurse and then I said impulsively, "You can check my temperature any time." 😅

Then I burst out laughing since that sounded as cheesy to my ears as I said as it probably obviously sounds to everyone else. Thankfully, she started laughing too and I was like, "I'm sorry, that was just lame!" I've never been good at delivering flirty lines and never bothered with pick-up lines (I'd almost certainly botch them).

Anonymous · Accepted Answer

This happened a long time ago when I was only like 12 but, there was this really cute guy I want to go to the dance with. Anyway, we had burritos for lunch at school that day D; and my stomach doesn't sit well with Mexican food any way every one got done eating and was hanging out in th commons area, I go to make my move and ask him out, I get about 3 ft. Away from him and accidentally let out a huge stinky fart right in front of him it was horribly embarrassing!!! :[ but it's ok, I went to the dance with my friend instead, word had it that he he was a jerk anyway who liked to use girls for money lol. Everything happens for a a reason, this is proof. (:

MemeSupreme · Accepted Answer

GOD why remind me... im ODing on cringe rn thinking about it

it's probably me using fuckboy lines on a crush in dms and sending a anime pic of a guy biting his lip after EACH line OR in 8th grade saying corny shit to hint to a guy i liked him lol shit like "im single like a pringle"

jennifer_bloom · Answer

I don't flirt, I smile and laugh and joke and compliment, flirting is romantic and not platonic.

AMS700CX4u2 · Answer

I was definitely at least 3 years behind my peers in high school. It was my senior year and I had gone to the grocery store to pick up a few things for my mom. One of my classmates popped up from another isle and yes she was one of God's beautiful creations. We started a conversation about one of our peers who had always been a braggart. It seems he had ended up one the short end of the stick in one of his adventures. Now came the time for the quip. The time for the funny reply. I meant to say "My Heart bleeds Purple Peanutbutter for him". but that is not what I said. "My heart bleeds People Pernutbutter" is what I said. She looked at me and repeated what I said, then walked away. I felt like a deflated beach ball.

itsclearlynicholas · Answer

And you got his number? Lol. Anyways I for one have had a few awkward flirts, as always everyone's been there, I attempted to flirt with a woman at like an eatery once, smiled politely then turned her back and resumed ignoring me, as if I'd never entered, and thankfully never saw her again and avoided that place for a long while. Lol it wasn't my regular eatery anyway. One time I try to be smooth and ask a woman her name, she eventually says it and also proceeds to ignore me. It seems that women, just not like my looks or the cut of my jib striking convo's that are beyond small talk even though I'm attempting small talk and there ya go. Single as a Pringle i am 🍟 ♂️

Wajahat007 · Answer

My most embarrassing attempt at trying to flirt with a very attractive girl happened during my college days. I had specially put on a tight t-shirt and equally tight jeans to show off my well chiseled body. But I of course forgot to do up my zipper. So I approached this lady with a very confident stride and asked her out. She smiled, pointed at my groin area and just walked away laughing…! I just went red and froze right at the entrance door to the lecture hall. Other girls too noticed my discomfort and quickly realise what was amiss:-) I felt like dying of embarrassment…

Paul09 · Answer

I went camping with my brother. Then we went hiking. Meet 2 girls hiked with them chatted. Half way one friend powers to end the hike. Still talk with one of them. Get to the end. I was curious what one of the Asian girls nationality was. I think I worded it wrong I said like what's your race? She got frustrated and said I'm Canadian! Or was she Muricans. "People always ask me that ". I felt like shit. We said goodbye and left.. I'll never forget that moment. And it's rare I get to flirt, I'm too scared to offended women. So don't really do it anymore

Wiredone · Answer

I've had a few close calls but always managed to turn it around and still get a smile.

I once flirted with a woman who was sitting by herself kinda like in a daze. I said to her " hi beautiful are you thinking about me" As I finished saying it, her husband came over. I told him I just wanted to see if I'd get a response or if I should call paramedics since she seemed out of it.

That happened 4 years ago and I still talk to both of them on a regular basis.

worldscolide · Answer

Good god, that would have made me interested actually, and i would have tried to see if you were okay..

As for me, i dont really flirt, at least i never really did that, i never really did pick up lines either, i was always just straight forward. im weird i guess. lol

dustybiker2 · Answer

I was saved this by being really quiet around men I liked. They never knew I liked them until I forced myself out of that phase. Always joke around with everyone, but took focused manual maneuvers to talk to those that had my attention.

Youngbrain · Answer

I don't think it count has a worst attempt but I gave a letter to a guy and he got teased by all his friend for it so he trew it on the rooftop😅

MatureSexyClassy · Answer

A good guy would be more caring and see if you are ok. I don't care for his reaction. Might be a guy you were lucky to steer clear of, honestly. Just my two cents.

7Phoenix7 · Answer

I don't have one lol in real life I'm not actually attempting, just being myself

Sweetascandy1990 · Answer

I am a very anxious and shy person so I usually am awkward when I like someone. I make no eye contact and stutter when I try to give a guy a compliment. I also get very soft spoken.

Lynx122 · Answer

I knew I was really awkward and didn't understand other people when I was younger so I didn't try this much.

JayBones · Answer

I was a teenager at the Jersey shore. I got whipped out by a wave and crashed into an older chick's legs. I looked up at her and said "bond, James bond" I don't think she even knew who James bond was.

robhazelnut · Answer

Impressing can fail. Flirting is a state within.

MushyKiwi · Answer

oh god... But he is a jerk if he didn't ask if you're okay.

Nikki1989 · Answer

If I ever flirt it is purely by accident.

DarkWinterNights · Answer

Every attempt I make at flirting is worse than the previous.

Anonymous · Answer

when i was 12 or 13 i must have been really bad at it because i would have done anything any boy wanted and no one would even ask me

elaphe · Answer

I called a girl from school and when I told her who I was, she did not know me by name. I had to explain who I was (I'm Lisa's brother from your English class).

What was your WORST attempt at flirting?

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