While many Gilmore Girls fans enjoy Rory and Logan's relationship, viewers often debate Rory's boyfriends, Dean and Jess, as she dates both of them during her high school years. But Rory has another major love interest while at Chilton, and that's her wealthy and confident classmate Tristan.

Related: Gilmore Girls: Every First Kiss, Ranked

While Tristan seemed like a jerk at first, since he insulted Rory by calling her "Mary" and teased her at every opportunity, Rory got to know him and realized that he might not be so terrible. It's true that Rory and Tristan never officially dated, and she continued her romance with Dean, but what if Rory had made a different decision? When thinking about Rory's love life, it's interesting to compare Tristan and Dean.