Flirting Fails: What's your story?

I've decided to make this topic because I think a lot of us on this site struggle with flirting with the opposite gender, myself included. Might as well have some laughs about it! I'll start it off by telling a story about how I goofed up so bad I had to just walk away. So I was at this bar waiting for my brother and a girl came up to me and commented about how hot my butt looked in my jeans. I'm an introverted guy who was totally not expecting to get approached. I just got so nervous I opened up with a story about how I recently ripped an old pair of pants trying to pick up my cat. So smooth.

Alright here it goes....so it all started when myself and a few friends went out to Dennys to get something to eat and so our food comes and the waitress who brought the food out looks at me and says"you have really pretty eyes!" and it kinda caught me off gaurd so I responded with "well...thanks..."! I also added a little awkard laugh afterwards which did not help with the situation. So as she left she said "Enjoy your meal" and my retarded mouth just had to say "YOU TOO!" which did not make any sense due to the fact she wasn't eating anything! At that moment I knew I could never handle the 'YOU TOO' phrase!haha and thats just one of my many fails! Hope everyone enjoyed this story!haha

Haha, mine usually revolve around a girl hitting on me and me not even noticing it. However, there was this girl I had a major crush on in high school. I finally worked up the nerve to go talk to her and when I opened my mouth, I started stuttering over every other word. I don't normally stutter :(

hahaha, I guess you can call that a Denny's disaster. I generally refrain from using "you too" anymore because I know I'll eventually screw it up again. Nate, at least you had the nerve to try. I never got the courage to talk to most of my crushes when I was in high school.

I don't take compliments very well. Actually I usually only get compliments on the shirts I wear. Go figure. But any time a girl says something nice about something I'm wearing all I can say is, "Thanks!" and I walk away. That or I get super defensive, paranoid or downright weird. The last time someone asked if I was a brony what with Derpy being on my shirt, and I was like, "Heck yeah!" And she said, "So's my boyfriend. I dunno why I'm still with him. It's all him and his friends talk about." My brain was all, "Abort! Abort!"

"Hello" Seen at Jun 02 15:36 "Hi" Seen at Jun 27 20:10 "Hello there" Seen 18:45 Or the all time classic "Hey long time no chat" *blocked reported etc*

lol I have the same problem nate, I can never tell, I also have no idea how to flirt I just usually just also say thanks...

I had the perfect set up, but I'm not single. It was simple too...All I did was comment on wanting tortilla chips as I saw some chick get some, to which she replied " I'm just having a lonely movie night." and all I could say was...well...MY GIRLFRIEND would probably want the chips...then awkward silence as we part ways.Not particularly a flirting fail, more like a chance that could have been if not for my situation.You single men need to realise just how much opportunity you really have and how simple it really is.

I don't know, Yaasshat. It's a lot more simple to some people than others. For me, I'm 5'4" and that's a highly unattractive trait, so women over 18 rarely flirt with me. But what you did say in that situation is good for guys who want to open up conversation with women without seeming creepy.

@arc, I don't think the height thing is as big of a deal as you might think it is. After all, if women were just attracted to tall men, no one except NBA players would ever get laid :/