Please Help With Valentine's Crush Idea?

It's a good idea, but that list a little excessive. A song like "Gotta Be Somebody" might be too serious for this particular situation. "I Want You To Want Me" and "Crush" are both really good picks. I personally would narrow the list down to about 12 songs. I think writing a cute note and putting it in the CD case slot would be a good idea. Just don't make too deep and heart-felt since the two of you aren't in a serious relationship, because you don't want to freak him out or scare him away. And that idea about putting something like "Let's hang so you can tell me what you think" is a really good idea.