I hear what you are saying though. It's about building up that level of trust. Who doesn't want to be the first hello in the morning and the final goodnight of the evening? Which the pattern did set day 1 and 2?

It might be important here to play it "cool". That doesn't come easy as one of your posts mentions worry about being "enough".

He's been single since earlier this month. It's Thursday, what field of work is he in(vague being more than ok)? Payday? Does he exert self control if drinking, for instance? No drunken drama? :\
Basically logically think him over. Oh yeah...nba draft night...is he into sports?
Things like that...