He's saying stuff that makes him feel better. I don't think he is really trying to tell you anything with it. He wants to think saying goodbye is getting easier. He wants to think that what he is going through is normal. I think the "we" things could well be habit. As far as school goes, he probably sees it as a good thing, whether you are together or not. Even if you are D'd there is going to be a connection between your success and his wallet. (On the other hand, I think he actually does care about you, and the school IS a good thing, right?)
I don't think he is reasdy to say he wants to be with her. I Think there is a little voice in the back of his head saying, "If the baby isn't yours, you can go back to Corey, like nothing happened!"
