I'd be concerned.

Unless there are other facts that suddenly provide a new, different context- the things he's saying seem to be quite subtly emotionally manipulative and also a bit bizarre - did he actually say he was going to come by the places you hang out, specifically to see you? Um, what? I'm struggling to think of any context where this can be a valid thing to suggest to a client.

The very fact that you're a bit worried about it means to me he's not doing his job right by explaining what he means with these comments, even if he means them innocently and the intentions are good he is not communicating effectively (as you're not quite sure what's going on) and that's not okay. Not good enough.