I think your therapist cares but us conflicted because he doesn't want to encourage the belief that this is a friendship and not a client/ therapist relationship. Again, it's not that you're doing anything "wrong" at all. Only your T knows if your pressuring him or not, but if he says it's ok to send texts emails and songs to him, then I'd think he doesn't mind. He does have other priorities however, so I really think you should examine how that makes you feel. If continuing outside contact is what you want you need to understand you may not always get the response you are looking for and be ok with that. If you aren't, then I might back off the contact or take another break.