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10. And he was the only one who could talk some sense into her.
Jess knew exactly what Rory needed, even when she didn't herself. Again, the parallelism here is really beautiful –– and effective.

"I know you. I know you better than anyone! This isn't you," Jess tells Rory, breaking through her apathetic facade at a time when no one else can get through to her. (Sorry, Lorelai, you tried.)