“Were you hanging out there with Dean?”

JESS: Were you hanging out there with Dean?
RORY: I was not hanging out with Dean. We were both hauled in there to watch her try out material and we were sitting in the same area so we talked a little, and then we left at the same time. That was it. It was all by accident.

Jess confronts Rory with the knowledge that he knew she was with Dean, something she omitted when recounting the events of her day. Keeping this from him possibly reminded him of the all the times Rory omitted to tell Dean when she hung out with Jess.

Unfortunately, due to Dean’s temper and jealousy, Rory learned not to be transparent with her boyfriend – a legacy which Jess is inheriting (which he sort of deserves, since it’s because of him that Rory was most often lacking in candour with Dean).

Unlike Dean, Jess quickly recovers once he realises it was just by chance Rory and Dean spent some time together in public as part of a community event. He asks her to think about letting him know in future, because it’s a shock reading it off a flyer, and then he asks her to spill all the tea on Miss Patty’s show.

It’s seems like a much healthier relationship for Rory, from this perspective, as she no longer has to fear her boyfriend finding things out and putting a suspicious spin on them.