RORY: Come on, let’s go to the carnival.
JESS: I don’t go to these stupid town things. [puts an arm around her]
RORY: You went to the Bid-A-Basket festival. You went to the dance marathon.
JESS: That was when I was trying to get you. I now have you. That means I don’t have to go anymore.
Well, here’s a chance to do something together besides kissing: Rory asks Jess to attend the Winter Carnival with her. However, it turns out he is quite resistant to the idea, saying that he doesn’t go to “stupid town things”.
When Rory points out that he went to the Bid-on-a-Basket festival and the dance marathon, he says: “That was when I was trying to get you. I now have you”. It’s honest and blunt, but also rather chilling. It makes it sound as if Jess was never really interested in Rory, except as a prize to be won. And being told only two months into a relationship that the other person no longer feels like they have to make an effort for you is pretty harsh.
Jess hasn’t had the best relationship models, so you can understand why he might not be the most romantic boyfriend in the world, but this can’t be what Rory was hoping to hear.