Help with a shy guy! Will choose best answer.?

I also have a similar problem in figuring out how to have a conversation. But first of all he's obviously interested in you. Second, there are almost always going to be times when you can't think of something clever to say, it's okay. You can just say you can't really think of anything too much. Three, don't get so worked up about it. You want to get closer to this guy and know more about him, and let him know more about you, right? Trying too hard to be something you aren't can backfire pretty badly.