RORY: Maybe Duncan and Bowman aren’t the best people to be hanging out with. They’re not as smart as you Tristan, they don’t have what you have going for you. They …
TRISTAN: You know, I’m gonna have to bail before we get to the whole hugging part. And ask your boyfriend to remind me when it’s coupon day, okay?
Rory tries doing a bit of bad boy renovation, but it doesn’t work on Tristan the way it seemed to on Jess. Unlike Jess, I don’t think Tristan is doing the bad boy act to impress Rory – they hardly seem to have interacted this term until now.
The major difference between her talk with Jess and this one with Tristan is that there is no anger (no passion) like there was when she berated Jess for making things harder for Luke. I think Rory does care for Tristan, otherwise she wouldn’t try talking to him seriously and telling him how smart he is, but it’s gentler and more pitying than the way she is with Jess, or even Dean. Tristan resents this, and is quick to leave (a foreshadowing of his final “bailing”).
Jess has had a much tougher life than Tristan, but Rory never pities him, mentions his past, or gives him a sweet sisterly talking-to, and I think Jess probably appreciates that.