Rory and Jess are the perfect definition of “right people, wrong time”
When they first met, Jess was at a weird spot in his life; his mom was out living her own life (without him). Leaving Jess with no one, since his father left Jess at a young age. He moved to a new town, with an uncle who he had never met until that very event. And because of the way he grew up, with no supporting parents and no true goals, he just never felt the urge to do good in school. Meanwhile, Rory was set on her life goals. She had a supporting mother, and many other loved ones in her town that cared about her. She got advanced learning that would open the way for her to go to Harvard, and other amazing colleges.
Jess was just trying to figure himself out, and what he wanted to do with his life. While Rory already knew. And because of this, both of them just didn’t seem to work-at the time.