Background: recently got out of a very long term relationship, almost 30, have not asked for anyone's number yet and I'm trying to overcome my fear of approaching women in general.

Was out at a pub with friends around dinner time. Waitress was pretty cute, age low 20's.

She brings me the cocktail menu, tells me only the beers chalked on the wall are available, those on the menu they ran out of. I commented something like "Wow you guys polished off all those beers back there? You know you're not supposed to drink on the job right?". Then I ordered an Old Fashioned.

She has some interesting but also weird star earings hanging down from her ears. I say "What's up with those star earings?" She says "Oh yeah these? I stole them from my mom for the night, do you like them?" I say "Well I think they might look better on your mom, mainly because they look just alright on you."

She brings me my old fashioned. I say "There might be a problem here." She says "What's up?" I say "You didn't spike my drink cause I insulted your earings, did you? Will I be okay after drinking this?" She laughs and says "No I don't feel insulted". I say "Well anyways I apologize, those earings actually look kind of okay on you. They match your skin tone. It's just I think you'd look cuter without them."

She actually starts taking off the earings to compare how she'd look without them on. After some back and forth and trying a few things, we settle on her wearing both earings on one ear, which actually looked pretty dope on her. She continued to wear them both on one ear the rest of her shift. Sick.

I'm now totally involved with my friends the rest of our stay, and don't pay anymore particular attention to the waitress. Eventually we want to leave, so we ask for the bills. It's my turn to pay. I say "Looks like you still got em both on one ear. And hey, don't think that I'm gonna give you a bigger tip cause of all the flirting you're doing with me" She says "haha no no I wouldn't do that. And thanks for the fashion advice." I say "You're welcome, you should be tipping me something as well."

And I wanted to ask her number but I didn't. And I feel way shitter not asking than to ask and possibly get rejected. The interaction was mostly strong and polarizing, maybe a bit too much. I feel like I laid it down hard. It feels shitty and I just had to express myself.

Thanks for reading. Any thoughts, positive or negative, are appreciated. Give it to me