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The Most Heartbreaking Star-Crossed Lovers In TV History

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10. Rory Gilmore & Jess Mariano, 'Gilmore Girls'
Okay, so there's still hope that Rory and Jess will end up together on Netflix's Gilmore Girls: A Year in the Life! It's hard to get over how things ended between them, though. Sure, they were teenagers, and it took Jess sometime to outgrow the whole sexy, brooding, jerky vibe, but he eventually became the dude that we all wanted him to be. Still, it really wasn't enough for Rory by the end.