Most Helpful Guy
He's obviously trying to test the waters with you, to see where you are at with him.
Second I think their is someone else in the picture, which is the reason you don't get to hear him for months.
He's probably uncertain of his position with you and also how things are proceeding with that "someone else" so he's trying to hit 2 birds with 1 stone.
In time everything would reveal itself, you just sit back, relax and watch it all play out on its own, without you being an active participant in his whole fiasco of his.