'Gilmore Girls' character Rory never broke up with her boyfriends, they all broke up with her.

Dean breaks up with her the first time because she reacts badly to him saying he loves her. He breaks up with her the second time because of her friendship with Jess. Jess doesn't so much as break up with her as he just disappears and their relationship ends. Then Logan and Rory "take a break" after a fight about Jess, which Logan interprets as a break-up. Then, after they get back together, Logan proposes to Rory, but she turns him down, which isn't technically a break-up but sure is close.

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