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A couple of random thoughts.
Emily and Richard's fawning over Logan and having him over for dinner was as expected. Their approval of Christopher and Logan and their complete disdain for Luke and Jess is yet another obvious, but appreciated parallel between the boys.
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I never formed this association before you brought it up but it's definitely an interesting parallel. I was definitely annoyed at Emily trying to sabotage Luke and Lorelai's relationship even though it seemed like she liked them together in S1 (with her noticing that they had feelings for each other).
Also Richard never did get to meet Jess? I actually feel like they might've gotten along with their love of literature