Here's the background: I patronize a restaurant near my work, I come in for lunch once or twice a week, always $5 tips on $11 dollar meals, well liked for giving them a lot of business. Cool with the owner, get a free burger now and then. The coveralls that I come in wearing imply that I've got a good paying job.(It's okay) I think the coveralls combine with tipping well and eating frequently imply that I've got money. My reputation there might also assist in getting any attention from... Tada! The new waitress. Cliché right?

Anyways she works evening so I just decide to be more quiet/stoic when I see her, if I don't prepare myself to run game, I will say some stupid shit. So one night I'm hungry, place is empty, more hanging out with the staff than I am eating. I get her cornered and start teasing/flirting, she moved here recently, bla bla bla, she lives in the trailer park, doesn't have a phone but has an address. Works every day but Sunday so I give the old "com'on let's go out Sunday night we'll have some fun."

The problem is her body language wasn't all there for positivity and I suspect that she really just wants me to spend a lot of money on her. No phone and I know she stays with her grandma in the ghetto trailer park. Maybe she wants to take a slice for herself out of my income. My current plan is to just go have a fun time, see where some escalation gets me, and either take or home or back to my place.

Any helpful advice /r/trpgame, choice words? I'll try my best to follow y'all's helpful directions, but mostly just gonna have fun with date night more than anything. Also this is my first date in a year, looong dry spell, I'm 19 she's 20.

Edit: This was typed on the job so bear with me, feel free to ask me to clear up any details.