<p>OK, here’s what my guy/friend/both did: tested the waters first. Started asking me to hang out with just him, which wasn’t unusual, but we’d do things we would usually have done with a group of mutual friends beforehand, like go out to eat or head up to starbucks, to the point where I couldn’t tell if we were hanging out or going out. After about a month of that he changed his wording slightly: “hey I’d like to take you OUT to this place if you have the time after [insert school function here]” (caps mine). Gave me the perfect opportunity to reject him without being awkward (though, of course, I didn’t say no and we’re still good, and I’m fairly sure he’ll remain one of my best friends even after we break up, so there’s that). So, uh, be smart and subtle about what you do, take hints, and if it gets awkward, back off. But at least give it a try ;)</p>