I don't know if Caleb was trying to be chivalrous but he pretty much turned it into Amber being into him rather he liking her. I mean, saying "I see you looking at me throughout the day" isn't anyway to try to pick up a girl.
EDIT: Amber's overall demeanor with Caleb talking to her may have her moving on up on my list. Amber is not about the Caleb life, lol.