Why did Rory and Jess break up? First, a little background on their relationship. Fans first meet Jess, the quintessential misunderstood bad boy, in Season 2. After getting into trouble at school ...

Season 2: Rory Is Caught Up In The Dean/Jess Love Triangle Jess, not Logan, makes his Gilmore Girls debut in season 2. He throws a wrench into the Rory Gilmore boyfriend timeline by turning her ...