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lol EXACTLY. What exactly do they base this "he knows her so well" off of? Like you say, he knows her teenage self, but he doesn't get her at all as an adult. Lorelai isn't the same person she was at 15/16 years old, she has changed since then. Chris gets her on a surface level, but it's Luke who truly gets her. He gets her on a much deeper level.
Luke is the one who has listened to her over the years, has seen her for who she is. Chris, until season 7, spent no significant time with her, so how the heck does he know her so well? And then season 7 showed us just how little he does know her, because both of them basically revert back to being teenagers and obviously as we see, can't make it work. If he knew her, he would have known she didn't want to get married in Paris and more importantly, he would have known how important it was to her to have Rory there.
That's another difference between Chris and Luke. With Chris, his feelings and wants come first. Rory comes second. With Luke, he recognises that Rory is the most important person in the world to Lorelai and will always put her and them first.
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