Aw, kid. I know you’re going to kick my ass for this, but take it from me.
Audacity wins the day, or, as I used to say (I used to be a bouncer) to those who didn’t know what “audacity” meant, "You can’t hit a home run if you’re sitting on the bench.
Stop asking so many goddamn questions and just go for it.
The messed-up thing about this whole male-female thing is that we all have unanswered questions. But the scariest and yet most rewarding thing that comes out of that is that there’s only one way to find out what the answers are.
Your whole entire thread is, “well, even if ‘a,’ then what if ‘b?’” And no matter how satisfying an ‘a’ there might hypothetically be, there will always be a fear-inducing ‘b’ as a corollary. But who cares? He’s not standing in your way, you are. You can run all the simulations you want. The only way to get the evidence is in the field. And here the eveidence is close contact and kisses. Worth the risk, I’d say.
Do as I say. Do it now. When you know his shift is up on a day when he’s got at least the next morning off, show up a bit before his shift ends. Be exhausted, parched, whatever. Say, “Hey, D. Gimme a [whatever it is you drink]. But I’m fucking shot, so come across the street and get a beer with me.”
He’s done with work. You’re a girl, and a pretty one. There’s your company and beer being offered and he’s got nothing to do the next day. He’ll go with, and then yu can talk just you and him. And if he doesn’t go with, then say, “Sorry you can’t do it, but I need that beer,” and go get that beer, because he’s not interested. Because no matter what I had going on the next day, if some girl I was interested in asked me for a beer,I’d at least go have one or two, if only to lay the groundwork for when I could spend more time with her.
Get off the bench, kid.