We had plans to meet up during a con, but were cancelled due to family issues. Now they are in a bad financial spot. The avoidant attachment style is something that we learned about while watching School of Life (we find them interesting.) in which they struggle with closeness in a relationship. There is a root to his intimacy problem, but I will not discuss it as that is when things get too personal. But he had a poor perception of love growing up, thinking that relationships were a waste of time due to the way people he cared about were treated. And yeah, it is pretty annoying. I’ve already asked him what he meant by “scared of intimacy” and he told me that I wasn’t necessarily the issue, it’s just that he has trouble creating emotional connections for another person. I wish I could get more descriptive about it, but I don’t want to hurt his privacy. To put it simply, even with friends and family, he has had troubles creating bonds with them. Frankly, I can’t say that these people treated him well, and I think that has something to do with it. Scared of being vulnerable. How long should I wait to talk to him then?