What do you think i should do?

So i haven't seen this guy in forever. We used to be best friends and then just lost touch. i saw him a little while ago and instantly it was taylor swift (enchanted) playing in my head. i really like him and so does my mom (like approves of him) but i don't know where to start. i want to pursue him, but how? we do not go to the same school and i hardly see him, but maybe that's just because we really have no reason to see each other yet.