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even as a Lit fan it still feels a bit forced to me
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It became clear to me at Emily and Richards vow renewal with Rory's conversation with Christopher about his and Lorelais first kiss and then Rory re enacts it with Logan. Even though she was mortified about being with Jess at a party, but I won't get started on that
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I think the bit that was forced is, out of nowhere, Christopher inheriting all of that money, so now both boys are sickeningly rich and can perform grand gestures at will. That was a bit too convenient to happen just as Logan appears on the scene.