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When she finds out that Georgina Sparks is not who she says she is, Vanessa confronts her and says she knows her real name, as well as her intentions. He tells her that he can't because it will ruin his friendships, and she advises him to do it anyway.
Vanessa confronts Dan regarding Milo's paternity and realizes that Dan has kept his son's existence from his immediate family. She grew up on a commune in Vermont before moving to Brooklyn to live with her sister, Ruby.
As a thank you for letting her keep Nate, Catherine gives Vanessa a check for ten thousand dollars. The Queen of Constance is therefore forced to comply, but conspires with Chuck to destroy Vanessa. She feels betrayed by both of them, since she still had feelings for Nate and since she and Jenny were such close friends. At a poetry reading, the two hook up, and Vanessa witnesses. After Dan sees him kissing Jenny, he gets kicked out of the loft but sends Jenny a letter confessing his feelings for her There Might be Blood.
Dan angrily shoots back at her, saying that his life was better before she climbed into his fire escape years ago. She advises Juliet to release them to destroy Serena but Juliet, worried about losing Nate, deletes them instead. Vanessa pushes him away because of this, but he confesses that he does want a relationship with her. Vanessa happily finds out that Dan loves her and discovers that Juliet was responsible for another blast against Serena, one stating that she was soliciting sex for grades.
As a result, they begin a friends with benefits relationship but finally begin dating in The Sixteen Year Old Virgin. By the end of the series, Vanessa and Dan are still together. She tries to help her plan a dinner for Rufus and his colleagues but Charlie sabotages it on purpose to blame Vanessa. The blond discovers a picture of them kissing on Gossip Girl, however, and embarrasses Vanessa by giving her a see-through dress, which everyone mocks at the Snowflake Ball.
Dan had been reluctant to publish it, fearing backlash against his friends for writing a novel that satirizes them. She decides to take his advice and afterwards the two enter into a relationship.
Willa calls her father to tell him about the snafu and is able to get the committee to review their applications. Fearing backlash against her, Juliet frames Vanessa for the blast, causing Vanessa to leave and effectively ending her relationship with Dan. Their plan works when Vanessa is humiliated but she later tells Dan what happened. At the end of the episode, they make up.
Dan lies about his whereabouts until Vanessa finds out that he will be arriving at a party with Serena. Someone nearly dies at the party, however, and when Vanessa catches a confidential conversation between Chuck and Blair on camera, it becomes the most sought-after item on the Upper East Side.
Later, Serena and Vanessa engage in conversation and get to know each other better. However, Blair feels that Vanessa is harboring feelings for Dan and warns her to back off his and Serena's relationship.
Suspecting a relationship between the two, Vanessa is shocked to discover that they are raising his son, Milo. When Nate, who is dating Serena, finds out, he sends a copy of the blast to Vanessa, who breaks up with Dan over it. When she explains to Dan what Vanessa did, he is willing to confront her himself but she asks to do it instead.
She lies to Vanessa that Dan told Nate he still has feelings for her, and Vanessa and Dan end up having sex. In the season finale, Vanessa and Nate catch up and become friends at the Constance-St. Vanessa and Jenny realize what Juliet did and both try to convince her to come clean. She seems to express some jealousy when she stumbles in on Dan and Serena about to have sex.
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