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On the surface, Nate seems to be the perfect "Golden Boy" of the Upper East Side.He is best friends with Chuck Bass, with whom he attends the elite St. Nate has been with girlfriend Blair Waldorf "since kindergarten".Novels: Sailor and lacrosse captain High school student (at St.

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However, he secretly harbors feelings for Blair's best friend, Serena van der Woodsen.

They shared a sordid one night stand before the show began, which caused her departure to boarding school.

His closest friends are Chuck Bass, Serena van der Woodsen and Blair Waldorf. However, Nate is shown to have deep, unresolved feelings for Serena. He reveals this to Blair in the first novel after Serena returns, and right before they were supposed to lose their virginity to each other, which causes their first breakup.

He gets together with freshman Jenny Humphrey, but later dumps her for Blair for being too clingy.

He is a fan of sailing like his father, and wished to do that instead of attending Yale with Blair, although he expressed interest in attending Brown University.

At the end of the series he sails around the world with a friend of his father's, Captain Charles "Chips" White to avoid getting in between Blair and Serena again.

In I Will Aways Love You, on break from Deep Springs College, Nate chooses Blair in part I and then Serena in part II.

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