<P> Nate Archibald is a lacrosse player at the elite St. Jude's School for Boys . His mother, Anne Archibald, is a French socialite, and his father, Captain Archibald, is a former Navy captain and a wealthy banker . His closest friends are Chuck Bass, Serena van der Woodsen and Blair Waldorf . </P> <P> He has been dating Blair since middle school . However, Nate is shown to have deep, unresolved feelings for Serena . They have sex during the summer at a wedding . 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 and Blair have an on - again - off - again relationship throughout most of the novels . </P> <P> Nate's family resides in a stately townhouse off Park Avenue on the exclusive Upper East Side of Manhattan in New York City, and his mother's French socialite family owns a summer chateau in Nice . 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 . </P> <P> Nathaniel Archibald was born to Captain Howard Archibald, a successful business magnate, and Anne Vanderbilt Archibald, a member of the Vanderbilt family . 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. Jude's School for Boys . Nate has been with girlfriend Blair Waldorf "since kindergarten". 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 . Nate's feelings for Blair are complicated by his ongoing infatuation with Serena and his parents' determination to keep him on a certain path . He later goes on to attend Columbia University . </P>

What season does nate and serena get together