Erm... Maybe. I guess it depends on things like the guy in question, the situation and the song.
Is there any way of singing in front of him but in a less personal setting? It's a good way to get him to notice your talents, without being awkward for either of you.
For example, if your school has a talent contest, or maybe you could organize a live show or performance for friends... That way you'll also benefit from the "group" effect of everyone admiring you on stage, making you even more interesting!