You may be right about feeling that he came to the ride for social pressures, but at least he is not avoiding being with you in public, and still manages to act like a couple with you. That's pretty big.
I don't know where to begin with all the great progress you've had: playful stuff with the sweatshirt, he CAME into the bedroom while you were there, initiated jokes, sounds like you had some in-depth and long conversations, invited to go somewhere with you and stop off at stores. Sounds also like he was letting you in by purchasing something major in front of you, while he has $ probs and you know that.
Is this the breakthrough you've been asking for? Sounds like the ice wall is chipping away....take some time to enjoy your success.
