So... there's a girl who works at the restaurant in my office building, she's attractive and I've built up a bit of a repertoire with her. But facts are facts; I've waited way too long to "make a move". In truth, I don't even know what "a move" looks like, or if I'm even capable of having any success with one.

In any case, I basically see her once or twice a month for the past year. She definitely had a thing for my old coworker, but he never made a move (in a relationship) and doesn't work here anymore.

Anyways, I'm terrible about just never making a move, or waiting way too goddamn long. But because I've never actually had any success, I'm gonna need advice from you guys about "your best chances".

So, say you meet the pretty waitress/bartender near work like I did:

  • How long until you make any sort of move?

  • What does said move look like? Do you go all-in with "Hey, would you like to grab dinner sometime?", or do you go more chill, like "me and some friends are going to a concert, you should come" (nevermind the fact I don't have friends, or go to see music). Or even more chill, like "My roommates are having a big get-together at our place, drinks and games"?

  • What are everyday situations that are wouldn't be made awkward by asking someone out? For example, there's a woman I met a few weeks ago that just started in our building (not my company), I've bumped into her a couple of times, would it be weird to ask her out in any sort of capacity, like to grab lunch?

  • Really, what situations are there BESIDES BARS that you could realistically expect to meet a woman and get a number or plan some kind of date?

Any and all advice is much appreciated. I have no idea what the fuck I'm doing, and really appreciate you guys' input.