How to flirt with this guy at the bus stop?

Wow that sounds lame..
I take the bus to and from sixth form college everyday and there is this one guy at the bus stop on the way back home almost every day. I smile at him sometimes upon seeing him, out of recognition, and he smiles back, but we’ve never really talked. I know he is from the all boys sixth form college nearby as last year he wore the uniform for the lower school, so im assuming he moved up into the sixth form college.
Anyway, besides my quasi-stalking of him, how do i initiate a conversation. Please do not suggest anything stupid like winking or licking my lips or whatever other rubbish. I don’t want to chat him up necessarily, just have a run of the mill intelligent conversation with him while waiting for the bus.

My friends suggested maybe i accidentally-on-purpose drop an item to see if he helps me pick it up and start a conversation by saying “oh glad it didnt break” or whatever.
But to be honest this sounds kind of dumb. I am not a very forward person and he seems kind of shy too.
How should I go about it so I dont look weird?