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In Season 5 , Nelly, still remaining a student at Yale, is invited to return to tryout to become a bridesmaid at Blair's wedding but doesn't show up because she hates her and is replaced by Charlie instead.

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Serena later finds out that he had known about where her father was since before they began dating, but had been delaying the information from her in order to get closer to her. At first he pretends to be a college student called James, but when Blair thinks he is boring, he tells her the truth.

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They start a relationship and she changes Chuck into a better more philanthropic person. That is, until Blair persuades her to help them in a plot to take down Poppy.

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