<P> In the first books, she stays away from Blair Waldorf and Serena van der Woodsen's social scene, resenting the Upper East Side way of life and preferring the company of Dan Humphrey, her best friend, and her sister Ruby . She has had a huge crush on Dan ever since they met on a fire escape when they were both locked out of a party, but Dan had always been too in love with Serena van der Woodsen to realize it . Dan and Vanessa finally get together in the second book, but break up when Dan cheats on her with a writer named Mystery . </P> <P> Vanessa is very fond of making dark films and spends most of her time filming people and objects . She later becomes friends with Blair Waldorf, and they become short - lived roommates . She takes much from her, becoming more open to the Upper East Side way of life and later semi-adapting to Blair's sense of fashion (though she once quipped that she would not be wearing snakeskin Manolos anytime soon) She begins a relationship with Aaron Rose, Blair's stepbrother, only to cheat on him with Dan come graduation . </P> <P> Dan and Vanessa once again become a couple, but with Vanessa taking a job as an assistant for Ken Mogul (and later a babysitter) and Dan cheating on her yet again with a leggy blond named Bree, they break up . Dan has a period of crisis when he thinks that he is gay after kissing a guy at work, but Vanessa stands by him . She agrees to move in with Rufus Humphrey (having been kicked out of her apartment by her sister Ruby and her new fiance Piotr) during the fall when she goes to NYU. Dan turns out to be straight, and they spend the time they have together before college being a real couple . In I Will Aways Love You, it was revealed that Vanessa grew her hair out . </P> <P> After a recurring role in the short - lived series What About Brian, Yahoo! stated her "capitalizing on that minor success" and eventually earned the role of "the stunning and unpredictable aspiring filmmaker ensconced in the highly dramatic lives of privileged teenagers on Manhattan's Upper East Side world". Szohr began her stint on Gossip Girl in a recurring role until her promotion to regular status in the show's fourteenth episode . Szohr said in Nylon magazine: Producers originally didn't want to cast her on Gossip Girl because her straight, shiny hair was too preppy . "I told my agent, you send every picture of my hair short, curly, black, blonde, I don't care ." In Teen Vogue she said the story of how she snagged her breakthrough role on Gossip Girl: "Two of my friends in L.A. invited me to this Labor Day barbecue, but I really just wanted to stay on the couch with my French bulldog," she says . They kept calling, though, so off she went . "I remember hanging out by the pool in an old T - shirt and jean shorts, just talking to people . Three days later, my manager calls to tell me that I'd been with the show's executive producer and one of the creators and they want me to audition ." Less than a week after that, Jessica was on her way to New York . "Nuts," she says . </P>

Who did vanessa end up with in gossip girl