Jamie thinks Hiccup is a pretty okay guy and that his ability to roll with all the terrible shit that happens to him (like having an alien rip out of his chest) is pretty admirable. He's under the impression that he should try to be a little friendlier to Hiccup since they had that thing in Fairplay and Hiccup's been pretty nice to him, overall, but being socially awkward and kind of a jerk Jamie's still figuring out how exactly he should approach this.