Most Helpful Guy
"Thing is, we decided to keep our thing going. I'm at a crossroad, because the more we hang out, the more he divulges to me about his life and the more into me he seems to be."
He is "off-loading" his unhealed wounds. People do that with their therapists in "talking therapy". It works for some people, re-living their unwanted memories and bringing a closure to them. Some people don't; they are the ones who use this technique to draw attention/care to them, and develop an addiction out of it. This kind is manipulative; they manipulate others using their past wounds, and suck others' energy out.
If he keeps repeating his stories like a broken record, having no intention of healing himself except moaning in eternity, you must put a stop to that. What you hope for, of course, is upon his dumping out his junks he gets healed and develop a healthy relationship with you.
Ask him, after he finishes one such off-loading "session" with you, is "Now that you have off-loaded those wounds, what are you going to do next?" This brings him to the awareness of what he is doing with you, and at the same time tell him you know what he is doing. It also puts him on the track of bringing a closure to the past, and step into a future with no more emotional baggages.
The one thing I am slightly worried about is that he said he knew he isn't supposed to do that, but he can't control himself; evidenced by his doing that. Tell him his happiness is HIS responsibility; not his parents', not his friends', not yours. If things get out of hand, tell him he should be doing this kind of off-loading with a professional therapist, playing the role of a good listener you are willing to do, BUT you are NOT professionally trained to handle "gabbage memories", and their source, namely him.0THIS IS NOT RELEVANT ANYMORE