<human>: I am usually interested in cocky, self centred guys but this time is different. I met this guy about 10 months ago and he's very interesting - he intrigues me because i've never met anyone like him. 

From what I can see he is useless with girls. He tries to flirt and although it can be painfully awkward sometimes it's funny and I like that he's out of his comfort zone. Anyway my problem is that I see him about once a week if even that and I want to move the conversation on from just the usual, 

"how have you been?"

but i'm not sure how. He's shy and awkward and I need a little help getting him to talk openly. I think he is interested in me but he skates a lot and seems to not focus on girls at all. 

I would do the "just man up and tell him you like him!" but I honestly think it would scare him away - i need to be more subtle about it.

I think we're incredibly similar in interests and mannerisms but I need to show him this. I'm open to suggestions on how to do so!

Can you give me the gist of the text in a nutshell?
<bot>: Like a guy that's shy and awkward with girls - how do I show him I like him without scaring him off?