Do you ever feel stupid flirting?

I'm the king of flirting, always have been. I pretty much become a peacock and strut my colorful feathers shamelessly every time I like someone. It never feels stupid in the moment, because one of the secrets to good flirting is genuinely convincing yourself that you're awesome and the other person must know it too, which automatically increases your outward projection of confidence and makes the flirting more appealing and more likely to work. It's only hours later when the fake confidence wears off that I realize what I did and think 'oh my gosh I can't believe I said/did something that ridiculous'.

For example with the hair thing, a basic version would be like

Me: 'your hair is cute'
Her: 'oh thanks, so is yours' (people usually respond with an equal compliment even if they're lying).
Me: 'what's your secret to keeping it so vibrant and healthy looking?' (extra compliments to make them happy, and catches them off guard since people don't go further than one comment usually which makes them pay attention to you more).
Her: 'Oh it's (answer)'
Me: 'That's a good idea, do you want to go out to lunch with me tomorrow so we can keep sharing fashion tips and looking at each other's cute hair?' (peacock mode activated, complimenting her again while also complimenting yourself projecting confidence).

 

Oh and if you ever feel like you said something dumb...I promise people have said much worse so don't feel too bad about it.

Probably the most cringy thing I've ever said was when I was 16. I met an older girl, probably 25, at the zoo who I liked. There was one of those 'pet the animal' exhibits with a cougar so we went and petted it. Afterwards we were talking about it and I was trying too hard to flirt but she didn't seem to be getting it. She said something like 'wow petting the cougar was so fun' and I stupidly looked her right in the eyes and said 'You know, I like to pet cougars too' (cougar means an older girl into younger guys). She just had this expression on her face like wow, those words actually happened, this is real life right now. Then laughed right in my face. Still got her number though haha.

 

I do things like this all the time. Either it comes off as just a platonic compliment, or I just say something stupid and screw everything up. Or I don't know what to say and I just keep smiling at them like a dope. I swear these poor young women must think I'm nuts. I just keep going, and try my best to not seem like a creep or an idiot. But it happens to the best of us. I did almost the exact thing that you did to this woman in the parking lot at Aldi's over the weekend. I just about lost it when I got back in the car, I was so embarrassed. Just remember that we all act like fools when we flirt sometimes.

 

Been there, done that. Pretty much anytime I'm in a store I manage to embarrass myself in one way or another.

 

Exactly! I'm gay, but I feel like I can mesh with guys pretty easily. I can just start talking, everything's fine, but with women I completely clam up and make a fool out of myself.

 

They definitely are.

 

My favorite color is green and each morning I go on a run. I'm not very good at coming up with usernames. You can call me Aaren if you like. Not my real name, but a nickname I use sometimes.

 

Cool, I've always liked the name Hannah. Thanks.

 

I do yoga sometimes, I do a little bit of everything. Not dedicated enough to actually gain muscle from it, but oh well. I enjoy it. I do it more to get out of the house and clear my head. Sorry for the delay, but I had to take the garbage out.

 

I have a very uncommon name due to a generations' old family tradition, so that's why I go with the nickname, but yeah, Hannah has always been one of my favorite names.