it sounds like you guys already have a friendship. i can understand your insecurity about being the one who initiates the contact but there can be many reasons for that besides the one you are worried about. for me, i never contact anybody. i dont mind talking to people, i am just fearful of making contact that i am bothering people so i never do it. if people want to be friends with me, they have to be the ones contacting me. also, some people dont need a lot of contact. two times a week is enough. they dont need to talk to the same person every day. ive got somebody who texts me every night and i sit there and wonder what i am going to talk about cause we just talked yesterday. it is a chore for me. so you never know. but you dont sound like he seems to dislike your time together. so why not ask for a meetup in your next conversation, just in a casual way say can we go out for coffee or something. i miss seeing you. the worse he can do is say no. no big deal. and if you do go out then ask if you could do it one a month or so. i dont think that is being too pushy. see how things progress from there.