I used to be super into him, but never was able to make a move. Now that I don't have to see him very often I might be able to make a move. Would it be weird to tell him we should hang out when we see each other at the office Christmas party?
Most Helpful Guy
It would not be weird. It would be very modern.
Advice on how to do it? Simply, with words, and with no expectation. If he doesn't react well, it's not the end of the world. Just don't have any expectation about an answer one way or the other. If he says cool, that's fine. If he hums and hahs, that's fine. If he says No, i have a girlfriend, that's fine.