Ask once. Ask directly. Be unambiguous about the fact that you're asking for a date, not just "want to be friends?" "Hi Jane. Listen, I like you a lot. Would you like to go out for coffee some time? If not, no hard feelings, and I promise not to bring it up again." Yes, it's awkward, but at work ambiguity will create problems. So will gazing longingly at your crush. If you can't work up the courage to ask, then you n…
I'm going to do this. May God have mercy on my soul. Any advice on how to meet her aside from creepily waiting for her somewhere?
Walk over to her desk?