5
It depends
We need a bit more context. What do you mean initiate?
It means he has dealt with people that didn’t want to date him after he tried going on a date with a person that it didn’t work out with
I mean initiate conversations, he’ll be near me sometimes and glance but won’t speak to me unless I say something
Yea that can mean a wide range of things tbh, sure could be that he likes you or it could just as easily be something totally different