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Serena invites Dan and Vanessa to stop by and they do.Meanwhile, Vanessa is trying to film Dan's life to create a short film to enter in a contest for grant money.They kiss at the end of the night and the next day Nate brings her to the SAT location, where he encourages her to take the test and keep her options open.She decides to take his advice and afterwards the two enter into a relationship.Vanessa makes her first appearance in The Handmaiden's Tale when she comes to see Dan after moving to Brooklyn to live with her sister, Ruby.
They partake in a long-distance relationship as she remains in the city (attending NYU) and he moves to study literature at Evergreen.
She lives in Williamsburg, Brooklyn with her unconvential sister, Ruby, and her only friend is Dan Humphrey, whom she happens to be in love with.
Despite her crush on Dan, Vanessa didn't dare confess her feelings for him, since his infatuation with Serena van der Woodsen had been all too apparent.
However, she hasn't forgotten about Dan confessing his feelings for her before she left for Vermont and is saddened when she hears he's dating Serena van der Woodsen.
When she confronts him about what he said before she left, he replies that he no longer has feelings for her as he's with Serena.
Before Christmas in Roman Holiday, Vanessa secretly submits one of Dan's stories to The New Yorker and it ends up being chosen to be published.