I'm trying to get close to someone I know who has shared that he feels like everyone leaves him and there will never be someone who stays, and that it caused him lots of shitty emotions and now he is trying to embrace feeling like it's ok if everyone leaves, he is ok on his own.

I support him in doing that too. I just have wanted to get close to him even before he shared that and have felt like he is affectionate towards me when we are together but does not cooperate when I try to set up meetings when we are away.