RORY: I have to go.
JESS: What? Did I do something or –
RORY: No, no. This was . . . you were – are . . . it was wonderful, and I look forward to many similar occurrences in the future, but right now, I have to go. Understand?
JESS: Not at all.
RORY: It’s more fun that way, isn’t it?
Rory has to go straight after the kiss because she is going to see Dean. Jess may not have found that explanation quite so quirky and charming. It feels as if Rory is being emotionally dishonest with Jess right from their first kiss as a couple. Unfortunately, one of the things she may have learned from being with Dean is that it isn’t always safe to be honest with your boyfriend.
Although seriously, apart from plot drama, did Rory really have to see Dean right after her first kiss with her new boyfriend? This also feels like “the games beginning” between Rory and Jess.
The Annotated Gilmore Girls 
“Unfortunately, one of the things she may have learned from being with Dean is that it isn’t always safe to be honest with your boyfriend.” <— Exactly!
When I first saw this scene when it aired all those years ago, I remember how liberating it felt that Jess reacted as if it was no big deal that Rory wanted to go, even though he didn't get why. It was such a stark contrast to Dean's ever increasing controlling behaviour and I felt so relieved for her in that moment.
Then, of course, she learned that there is another side to the "being totally cool" coin when Jess, at times, failed to be a decent boyfriend. But in this moment I think it was so well deserved for Rory to get a respite from having to adjust her behaviour to a guy's temper.
LikeLike
True, there is a feeling of her having escaped from Dean into something more accepting. Unfortunately, it feels as if Rory is still adjusting her behaviour with Jess to placate Dean’s feelings.
LikeLike
I’ve always read it as Rory feeling acutely guilty about being happy with Jess, and feeling the need to go to Dean to clear her own conscience rather than to make Dean feel better. Of course, it wasn’t the smartest move and it kind of backfired because, naturally, Dean doesn’t feel much like forgiving her. But she’s what? 18? You live and you learn. 🙂
Also, how believable is it that Dean hasn’t told his family about the breakup for two weeks and that none of them has heard it through the very chatty Stars Hollow grapevine?
Finally, thanks again for all your hard work with this. I enjoy these frequent deep dives into the Gilmore verse immensely!
LikeLike
Thank you! It isn’t believable at all – but the show always presented the town as having a “hardcore” of residents who gossiped and knew everything, and an outer circle who just did their jobs and minded their own business. The Foresters are in the outer circle. (I guess!).
LikeLike