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OK, I have a few:
I have a friend who's a real asshole, and I think he might be gay (those two things are not connected, by the way):
"Dude, you're an asshole. It's not cool, as you seem to think. By the way, are you gay or what? You should really break up with your girlfriend if you are (or at least let her know she's a beard)."
To one of my best friends (and this isn't in a Nice Guy kind of way, in case that isn't clear from the text):
"I think you are one of the most beautiful people I've ever met. I could definitely see us dating, but I understand completely if you don't find me attractive, or don't see me that way, or have some issues you need to work through, or anything like that. I'm completely fine with is being friends for the rest of our lives, I just wanted you to know."
Very annoying guy I've had a couple of Comp Sci classes with:
"Dude, stop trying to be funny. Nobody's laughing, not even the professor. Also, for fuck's sake stop trying to impress the professor with your vast intellect; you're only annoying them, and most of the time your smart-ass questions don't make any sense, and your smug delivery just makes it worse. Seriously, I want to like you, but you make it so hard for me to be civil."
And there are a couple of girls that I would like to ask "So, what is it about me specifically that's unattractive to you? I don't really care about you anymore, certainly not as a romantic object, but I need this information for quality-control purposes."