You two are not dating!! Your behavior does sound obsessive (not trying to be mean... just trying to be honest with you) and it is likely to offend him. If you hold your friends and loved ones so close that you suffocate them, they'll want to leave. However, if you relax and allow them to come and go... allow them to be free... they'll be much more likely to want to spend time with you.
Are you working full time? I really feel that once you get benefits, you should consider seeing a therapist. I'm not saying you need to be taking psychotropic drugs... just saying that you would most likely benefit from having a therapist who can help you to work on your depression, anxiety, obsessions and relationship skills.
In the meantime, try not to be so anxious about your roommate... constantly remind yourself that everything will be ok. Good luck.