Heather you sure know how to get our attention!! LOL
I really don't think it is creepy, maybe I'm missing something and should go back and read.
I think the guy likes your sense of humor and just wants to get to know you better. What is a drink going to hurt. BUT DON'T LET YOUR DRINK OUT OF YOUR SITE! If you get up to do something have your drink gone or take it with you.
I freak about city dating as you can tell.