When someone winks at you does it mean that they like you
this guy always winks at me when we look at eachother
No, it means; I see you or I notice you, if they like you lots there will be more then a wink. If he tries to get close to you then he likes you
It could be subtle flirting. However, if it is someone you're good friends with, then it could be just a friendly gesture.
Maybe or something deeper than that
I think In your case he wants to have closer relationship to you.