Ok, honestly?

It seems quite high-maintenance. I'm not trying to be mean - it just seems that if he's already irritated and upset because of the conversations that you're trying to engage him in, then a letter like this is likely to make it worse.

I can relate to your line of thinking, but being on the receiving end of something so intense can be really draining on the other person. It seems very needy and your friend may care about you very much, but it sounds as though he's made it clear that he only has so much patience to get involved in your neuroses. I do think you have great intentions, but I would probably not send the letter and would check myself when feeling tempted to text questions as you did.

I mean all of this kindly, btw.