Dr. Skipper, in my opinion what you're describing sounds a little unhealthy. It sounds like he wants to date, but not for the express purpose of growing closer to you. It almost sounds like a selfish need for emotional support. Basically he can still feel good about himself because he's dating, but avoid any of the emotional ties or work that goes with getting to know someone at an intimate level.

Now you should totally be friends and hang out and be there for each other in that way. But I'm afraid trying to dance that romantic line might end up hurting you or even both of you.