I really should have known better. [He really should have. It was kind of his fault.] Both times, now that I think of it.

[You're dead to him. Dead. A pile of dirt, that's you.]

I... suppose. [He can't really argue with that even though he's clearly unsure about it.] I was thinking of asking her to help me in one of our classes, that'd be alright, wouldn't it? [How is he asking Jake for romantic advice. What is this.]