PARIS: So where is your boyfriend?
RORY: We, um, we broke up.
PARIS: Oh. Well, at least you had a boyfriend for a while.
Although she is socially awkward, I think Paris genuinely means this to be comforting. Notice that Paris has thin braided pigtails among loose hair – the same way Rory did her hair for the Bangles concert, where she and Paris bonded. Paris must admire Rory to some extent to copy her hair style. Also notice that Rory is willing to tell Paris the truth about her break up with Dean, whereas she avoided telling Louise when she asked the same question.