Jess confronts Rory, and asks if she and Dean had agreed to meet up for the winter carnival behind his back. Rory truthfully says no, but admits that she and Dean did go out for coffee and talk, and decided they were going to be friends.
She points out that it’s a small town and they’re going to see each other around anyway, and Dean “never did anything bad to her”. There seems to be an immediate whitewashing Rory and Dean’s relationship after they break up, so that Dean becomes perfect in retrospect.
(Incidentally, I wonder how Rory would take it if Jess stayed friends with Shane, since Stars Hollow is a small town, and Shane never did anything bad to Jess? I have a feeling she would be furiously unreasonable about it).
Rory is worried that Jess will be angry with her (like “perfect” Dean would have been), but Jess says he isn’t. He does say that he would have liked to be told about it though, which Rory agrees to. This is the second time that Rory has seen Dean and kept it a secret from Jess.
She also doesn’t tell Jess that it was she who went to Dean first and asked to be friends. She says they talked “once”, which is pretty close to a lie – although Rory would say the first time they didn’t really talk, she spoke to Dean.
Unfortunately, Rory’s relationship with Jess begins with her keeping things from him and seeing her ex-boyfriend behind his back, so it’s not a very promising start.
The Annotated Gilmore Girls 