17 “Cute” TV Relationships That Really Aren’t Cute At All

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Rory and Dean, Gilmore Girls

Rory and Dean Gilmore Girls

The WB

Rory and Dean started out as an idyllic teen relationship — if there is such thing. Dean was a simple guy, but he was stable. He was always there for Rory, and the two got along well. When they try to reignite their relationship, things don’t go nearly as well. Things start when Dean cheats on his wife with Rory and she even has her first sexual experience with him while he’s still in a committed relationship with his wife.

From there, Dean seems to resent every part of Rory’s life that he isn’t involved in. Their relationship eventually falls apart, in part because it’s clear that Dean isn’t satisfied with his own life. Rory didn’t always engage in healthy relationships, but this time with Dean was the worst.

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