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it’s interesting that it’s kind of similar to when like Christopher would visit
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I think Chris was an ok fit in SH because in the beginning we don’t really see him as the heir to a fortune. He was just an immature guy trying to find his place in the world, happy to ride his bike and sleep on Lorelais couch. He wasn’t really made out to be the rich upper class guy until Logan appeared and the father died. In fact I think they made Chris to be more like Logan in the later seasons to fit the narrative, not the other way round.
I see a lot of Logan fans on Facebook say she should be with Logan because he can be just as comfortable in her SH world and her Emily Gilmore world, and I say....well you have just described Christopher.