From Friend to Boyfriend

This amazing girl I know just broke up with her boyfriend. We are friends, though not too close. I really like her very much and I think she'd be cool with being with me too, but how do I broach the subject of going out with her as more than friends without looking too shady? I don't want to wait too long, because she really is special and there will be many entreaties from many guys. Help!

The transition from "just a friend" to bonafide boyfriend can be tricky, but it can be done. However, there's a chance that if it doesn't work out you will lose the friendship you have - you'll have to decide if you're willing to take that risk. In this instance, we're not sure how long the girl in question was dating her former boyfriend or how painful the breakup was - both factors to consider when trying to gauge if she's ready to date someone else, and if that person could be a serious relationship or just a fling.

We think the best course of action would be to try to spend more time with this girl and get to know her better, thus giving you an idea if and when she's ready for a new guy and if that guy could be you. Ask her how she's feeling about the situation with her ex and dating new guys. If you're suddenly interested in spending a lot more time with her after a recent breakup we think she'll get the hint that you're interested in her pretty quickly, and you should be able to judge from her words and actions if you ought to make your move. Let us know how it works out!

Got a question? Need advice? E-mail ask@gothamist.com.