Have him talk to someone about his issues and have him talk to you about what's been bothering him most. Then listen, you're currently doing everything right. He needs assurance, but searching a certain kind of assurance of some way to reach out to you he is not comfortable doing or feeling like he is certain what he feels.

I've been in similar shoes, but that's how I used to do it, I wouldn't do it, because I'm worried, I don't care what the other person did would leave me or hurt me. I just wanted to feel safe from something that went wrong in my life, and needed someone's assurance, because I didn't received it when I needed it.

but I could be wrong altogether and he justs wants that certain attention like he gets a satisfaction out of making you guilty to come to his needs and if you don't he'll feel disconnect and worried about stupid ****.

I don't think he's a bad guy nor do I think he's reached that point. I'm just saying if he is willing to let go of his insecurities he'll find his own way to do that, and you must let him have room to do that.