The things he half wishes half dreads she will say.

This just isn't working, is it?
I mean, to be honest, I never thought it would.
But you know what's really great?
I'm not worried about you being embarrassed by me, or not all together interested in me. Because I'm not all together interested in you, either.
Well yes, I would like to say that it's not you, it's me -- but that's just not true. I'm equally guilty, but you certainly aren't innocent.
Your constant need to be the smartest person in the room, and to correct everyone's little mistakes is really alienating.
No, don't make it seem like you're doing us a favor. We know you're smart -- but more than that, we'd like credit for being smart too. Or at least an atmosphere of intelligent equality. No one likes a know-it-all. Especially when you don't know it all.
You know what else, you don't really laugh at my jokes, you just sort of scoff. Sometimes that scoff is paired with an eye roll, or a "you're so weird." The only way I know you think I'm genuinely funny is when you steal my jokes without giving me credit, even though you never tell me it's funny at the time. And I'm not saying I'm hilariously funny, but I have a pretty good handle on wit. Do you feel intimidated by my sense of humor?
I'm quirky and weird and silly, and I like these things about me. You make me feel awkward and stupid for trying to have fun. Cut loose for once and stop taking yourself so seriously -- no one else does.
But besides all that, here's the real clencher -- we don't communicate well, which really throws me off. I'm normally really good at communicating with my friends, and in general. I don't know if it's just me, or if everyone has the same problem reading you. While it frustrates me to no end, in some masochistic way it makes me want to stick around -- to maybe one day crack the code and have everything make sense, or to maybe get close enough so that you'll bring down that wall. But on the other hand, I have to wonder if it's really a wall at all, or if it's just you.
Also I've never heard a genuine or significant "Please" or "Thank you" from you. Not once. Those are two of the easiest things to say. I'm not saying that sort of thing is a deal breaker, but I think it's a pretty good indicator of potential appreciation.
We've had some fun, but let's just agree that we'll probably never agree.