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In the earlier seasons of Gossip Girl, Dan and Blair only associate because of their mutual friend Serena. They have a mutual dislike for each other (Dan thinks Blair is superficial and mean, Blair thinks Dan is gross, poor, and boring). Occasionally we see them scheme together to help one of their friends out. In later seasons, during one of the summer holidays, Dan and Blair are 'abandoned' by all their friends and the only ones left in New York. They begin to forge a friendship based on shared movie and intellectual interests. After spending the summer together, they start to question their feelings for each other, after a long history of hate. They kiss each other to see if anything could happen between them. Blair describes the kiss as an "life-changing" moment. Dan misunderstands this as unrequited love and begins to crush on Blair, even placing her as one of the nice main characters in his book 'Outsider'. It is then revealed that Blair found it "life-changing" because it showed her that Chuck was the one for her, not Dan. Dan debates to reveal his true feelings to Blair, but after a talk with Serena, he instead makes it is mission to give Blair and Chuck "the happy ending they deserve". He still likes Blair, but ultimately wants to see her happy, and he realizes this can only happen with Chuck.

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13y ago

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