“What do you and Dean talk about?”

JESS: Hey, what do you and Dean talk about? … I mean, does he know Björk?
RORY: I’ve played him some stuff.
JESS: Hm. So you got a teacher-student thing going?

Rory completely throws Dean under the bus at this point. She could have said, “Dean is a fan of Nick Drake, he actually got me into Pink Moon. And he loves Liz Phair and The Sugarplastic”.

She doesn’t mention that Dean likes old movies, and that they originally bonded over Rosemary’s Baby when they met, or watched Willy Wonka on their first date. She doesn’t tell him that Dean recommended Hunter S. Thompson to her.

The fact that she makes no attempt to defend Dean’s intellect, or even to tell Jess to butt out of her relationship with her boyfriend, is extremely telling. She does tell Jess that, despite his scepticism, Dean is exactly her sort of guy, but it doesn’t sound very enthusiastic – especially considering Rory couldn’t think of one thing she and Dean talk about.

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