I've realized that my connection issues with other people - feeling left out since a young age and never really being able to replicate the social dance very well - can lead to me becoming obsessed with people. When I finally find someone with whom I feel a close connection I will crush on them, heavily. And then I find that those who readily respond to my obsession tend to have connection issues themselves.
I'm just slowly waking up from a ten months obsession after I left a relationship of three years. I left for many good reasons but getting over him was the hardest work I ever did and on many days I felt I was ready to change the way the universe is put together just so I could be with him again. There was nothing going on in my brain for months, just keeping myself barely alive and thinking about this man and the relationship we had - everything else, skills, knowledge, ability to enjoy things, was gone. And then after much pondering, planning, and most importantly making sure my boundaries were where they needed to be I did return and had my heart broken again in several intricate ways. However returning was the right decision for me. The leaving, and the returning. I learned so much about myself. I watched my own obsession and sat with the grief, and the older grief behind it, and now I feel a little wiser.
You might return, it might not work, or he might say no - and then you get to learn a little more about your obsession and about yourself. It will hurt, you will have to cradle yourself through the heartbreak, but you get clarity about something you now might be missing. Just remember it's your obsession, not necessarily his obsession and you should be accepting of whatever outcome your attempt of re-connection brings. When connection is difficult it's no shame to go out there and experiment, that's how we get better at it and find out about our needs!