What are the funniest flirt attempts you have seen/experienced?

[SociableGuy]

Sometimes a flirt attempt just doesn't work out the way you expected and you're left with a very funny/awkward situation (eg. video below). As embarrassing as it might be in that moment, it often turns into a great story that you can humor your friends & family with for years to come.

[Chill_Meta]

Funniest I've seen would been when my marine buddy would come home to visit family and chicks would try to flirt or get his number. One time in particular we went to eat and this girl had her own personal "gain commercial" because of his cologne. She tried to sit down at the table and everything to get his number. When she had to go tend another table he said "hurry up and finish your food we're leaving! If you're not finished by the time i get up I'm leaving you here" lol still makes me laugh to this day.

Funniest I've experienced is when i went to the coast a few years ago. My little sister, at the time, was shooing girls off left and right lol. No matter where i went that day a girl have me her number. The tip of the iceberg that day was me going into a leather store. A pretty little chick made a b-line to me from the back of the store. She walked with me as i looked around and before i left she made sure i got her number as well. That one made me laugh the most.

[Guy13]

I did not know she had a male package... I mean he had a male package. I learned the most beautiful "women" in Asia likely have a man's package. That was embarrassing and fell under "to goo to be true"

[Hrumf]

I was out with a client and we didn’t know where the bus stop was. This guy offered to help and showed us where to go and walked with us. While waiting for the bus he was talking to another guy at the bus station about how his girl wants his money, and he was venting about his girl.


My client got on the bus and I went to go to the train. Keep in mind…I am as pale as it gets being a redhead. This guy, who is Latino and therefore quite tanned, approaches me, puts his arm out, getting ready to compare out skin tones to mine as a way to hit on me.


Can’t make this stuff up…

[Celeste951]

This wasn’t exactly awkward but I was at a highschool football game and some kid dropped something right in front of me then preceded to pick it up, looking at me, then saying “I think I just fell for you”. Probably the funniest thing that night

[Anonymous]

The funniest at the time that it happened was when a really drunk dude tried to hit on me and my best friend at the same time. He wasn't quite sure where to look, since there were two of us, so eventually he just settled for a spot on the wall in between us.

The funniest story I've ever gotten is funny in a more "how on earth did that actually happen," kind of way. I was fifteen and looked about eleven, and there was a twenty year old dude that I used to talk to online. (I thought he was sixteen). Anyway, we used to talk over video chat, and one day he just says, "You know, you have a very strangleable neck." I'm guessing I looked a bit freaked out, because this was immediately followed by, "Don't worry, it's a good thing."

The dude in the second story ended up going to jail about a year later. I don't know exactly what it was for, but I would not be at all surprised if it had something to do with child pornography. He never saw anything from me, and we never met in person, but it wasn't for a lack of trying on his part.

[19magic]

I've had a pm on this site before something like: you like cock then you must be thirsty for mine (insert cock pic), wanna Snapchat.
It was after me posting that no I'm not bi, I like dicks and sex with men. Or something on those lines.

I do have another one though when I was 14 I went to this youth club and one of the guys there said he wanted to see me and that I should date him as he can make me sweety bras and thongs (I can't remember what those necklaces/ bracelets are called, similar sweet feel and taste as love hearts).

[DryGermanGuy]

While standing in line I had to witness a guy (twenties, suit) hit on a girl working in the bakery. He was soooooo green and clumsy, I wanted to dig a hole for myself just to escape that. But mostly it taught me never to hit on salespeople at their job, especially with everybody else listening in... :-o

[yourpalval]

Dudes entire line was "your eyes are a surprise" like he thought all he had to do was rhyme once and I'd drop my panties

[SociableGuy]

I suppose if you told him F U he would be the one surprised :)

[Phoenix98]

It was awkward mainly because my buddy and I were making it that way unintentionally we were being assholes to each other as we do ( it's how we interact with each other ) while at the same time he was trying to flirt with this chick behind a sandwich counter. Oo man it was funny.

Lmao she said we were both weird and when we left I said he should go back in there and get her number and surprisingly she gave it to him to which I applauded him.

[D_Bone_Steak]

I had a very unfortunate old woman try and hit on me recently... I can't explain the cringe I feel and it's not cringing for myself.

[Lickmymeet]

EDP chat logs 🤣

https://www.youtube.com/embed/UthG_pTFqC8

[Jltakk]

I dunno, I find flirting cringe in it of itself tbh.