[He's actually legitimately concerned about the look he's getting and holds his hands up, as though calming someone down.]

Now hold on, that wasn't what I meant at all! [Well, some teachers from Hiccup's memories of high school didn't do much to help when he was being bullied, but he doesn't mention that.] I just meant the teachers could use a hand. No sense in using civilian arrest unless necessary, right?

[He does blink at the order to buy him dinner and pick him up...here? That's weird, then again, he knows where this is, but he could probably find wherever Jackson is staying easily enough. Still, if it was privacy the other man wanted...]

Well in that case, I may just take you up on that. Hope you like Italian, because I'm going to show you the best restaurant in town.