This may seem kind of dumb based on the title, but I (27, M) work at a truck stop restaurant. My job, let's just say at a major North American chain that starts with a D, isn't associated with the truck stop in and of itself, but is situated off to the side inside the truck stop. We would not be considered coworkers. There's this gal that works in the truck stop area that I think is cute. We've made a few quick small chats, mostly about work. Problem is, since their shifts start at a different time than ours, their break times are different as well. So at any given time, either one of us is on the clock. And of course, that means we have to be professional. She gets off earlier than I do, so her break is usually while I'm working. It's not uncommon for the truck stop workers to sit in a secluded spot in the restaurant from the noise (room behind the lobby) My question is, when and how should I ask her about her status and (possibly) a date?