Am I confusing friendliness with flirting?

This guy from school randomly decides he wants to get to know me so he IMs me and we talk. He tells me that I'm pretty and smart and flirts with me. I know he was flirting b/c during part of one our IMing convos he goes "i guess my flirting isn't as good as [insert name here]." He's seems like a decent guy & when we have texted and IMed we've talked for hours so yeah i kinda like him. It's like every guy i take an interest in is a flirt. If he's just a flirt i feel stupid for wanting to talk to him & sitting around hoping he might IM or text me. This isn't the first time this has happened to me & i'm tired of it.