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He used to be engaged to Jackie Molina, but she broke off the engagement with him in the Season 3 finale.

In the summer after high school graduation, he had a girlfriend named Maggie who got pregnant, but his mother paid Maggie to leave town and have an abortion.Dan and Serena finally get married in the series finale.Serena is regarded as the "it girl" of the Upper East Side.Serena Celia Humphrey (née van der Woodsen) is a main character in the Gossip Girl series of novels and its television adaption, in which she is portrayed by Blake Lively.Throughout the series, Serena has an on-again, off-again relationship with Dan Humphrey, the two have the longest running relationship on the show.

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