So there's this girl at my office who's almost obviously into me. I catch her looking my way making more than just casual glances frequently. She stares. Recently she mentioned that she would give me a recommendation if I need it - I'm quitting soon. So I said I may need that recommendation sooner than you think - let's get drinks one of these nights.

She said yes. She may be meeting with me because I'm a good contact for her and vice versa. Let's say that she's actually not into me, or maybe she is and doesn't want to hook up with a coworker. If I make a move on her like trying to kiss her and fail, it could mess with my professional reputation to some degree but wouldn't destroy me.

What's the safe way to go about this? I'm decent at escalating and closing, but usually failing doesn't have any real consequences. This time it does.

What if, if it's going well at the bar, I ask her to go to another bar. If she says yes, at the next bar I'll straight up tell her, "listen, I've never done this before, but I'm going to put my cards on the table. I'm interested in being more than just coworkers with you and seeing where it goes. What about you?". I like saying it like that because it's ballsy and assertive, and it doesn't make for as good of gossip. "backinthegame tried to kiss me the other night" sounds much worse than "backinthegame asked me to be more than coworkers last night".

Or maybe instead of saying the above, I could try to hold her hand, and see if she pulls away. Alternatively, there was an old kiss test I learned 10 years ago, if you can touch her hair without her recoiling, she'll almost always kiss you.

It goes without saying that I'm gonna be puttin on the charm and trying to get her to chase me rather than the other way around. If her body language and tone of voice aren't looking positive, then I'll give up and not even bother telling her I'm interested.