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I hate that he goes along with the relationship, pushing her, but then later claiming he knew he was pushing her, knew she was vulnerable and he knew she was still in love with Luke. Imo that's worse than if he was oblivious to it all and was genuinely thinking she wanted this.
But he was so desperate to be with her for his own selfish needs, that he pushed the reality of the situation to the side and put Lorelai through all of that. If he truly cared about her, he would not have pushed, let her grieve. Chris is just too selfish to really care about her.
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