"Okay, listen. After all we've been through, when you walked away tonight, all I could think is "she's the one I want to be with."
-Nate to Vanessa, It's a Wonderful Lie
Novel Series Edit
While both are central characters in the Gossip Girl novel series, Nate and Vanessa do not have any form of relationship.
Vanessa and Nate first meet in Desperately Seeking Serena, when he drops off SAT study materials for Dan Humphrey while he is studying with Vanessa. When they first meet, Vanessa is rude to Nate; as she thinks he is stuck up. However, she opens one of the study books he gives them and finds a practice essay he wrote on the struggle of constantly being in the middle of his parents. After reading the essay, she invites him out for Greek food and they bond while eating together. They later get together for date to see her sister's band and end the night with a kiss. They continue to hang out, and Nate learns that Vanessa is intelligent and scores almost perfectly on her practice SAT tests. When it's time for the real test, he brings her to the center and convinces her to test to give her more options for the future (All About My Brother). When Georgina Sparks returns to town and begins to blackmail Serena, Nate is able to give Vanessa her real story before she can continue being duped into believing Georgina is really a girl named Sarah (Woman on the Verge). He brings her to Bart Bass and Lily van der Woodsen's wedding in the finale Much 'I Do' About Nothing, but they break up soon after because he didn't have time for a girlfriend and it just didn't work out.
Once Nate returns to Manhattan, he begins to hang out with Vanessa again. However, his affair with Catherine Beaton gets in the way of their budding relationship. At a party at Blair Waldorf's penthouse, he tells Vanessa that he is going to end things with Catherine to be with her. Before he can, Catherine confronts Vanessa about dating Nate and blackmails her with revealing Howard Archibald's location if Nate leaves her. Feeling that she can't ruin Nate's life, Vanessa begins to distance herself from him (The Dark Night). In The Ex-Files, Vanessa learns that Catherine is sleeping with her stepson and Blair's boyfriend Marcus Beaton. She tells Blair, but after she mistakingly assumes that Blair isn't dealing with it, she tells Catherine's husband. However, she soon learns that was a mistake because Blair was able to convince Catherine and Marcus to leave town and pay of the Archibald debt. She tells Nate, who is more disappointed that Vanessa went to Blair instead of him. In The Magnificent Archibalds, Vanessa discovers a letter Nate wrote to Jenny Humphrey about how he has strong feelings for her. Jealous, she steals the letter before Jenny can see it.
Soon after, Nate asks Vanessa to The Snowflake Ball. Meanwhile, Jenny, who still has some unresolved feelings for Nate, teams up with Penelope Shafai, Isabel Coates, and Hazel Williams to bring Vanessa down. She creates a see through dress for Vanessa, and they plan to shine a bright light on her at the ball to reveal her underwear. However, Vanessa feels guilty for stealing the letter after talking to Jenny and plans to tell Nate at the ball. Before she can, the girls spotlight her and humiliate her in front of everyone. She leaves the ball, but is followed by Nate, who reveals that even though she stole the letter he wants to be with her. They enter into a relationship. After a long fight with the van der Bilt side of his family, Nate is convinced by his cousin Tripp van der Bilt to attend the family reunion. He brings along Vanessa and Dan Humphrey, and they meet his family. At a party thrown by his grandfather William van der Bilt the next day, Vanessa learns that Nate might abandon their summer backpacking plans to take an internship at the mayor's office. Angry that he might become a van der Bilt robot, she encourages him not to take it. Meanwhile, Blair is spiraling out of control and Nate is able to talk her back down to earth and they begin to grow closer (The Grandfather). In Remains of the J, Nate breaks up with Vanessa due to him feeling things have come to a natural end. Thinking he dumped her for Blair, she teams up with Chuck Bass to get revenge. At Jenny's Sweet Sixteen party, they stage a kiss in front of Nate and Blair. Nate becomes disappointed with Vanessa, and asks if that's her way of becoming more like Blair.
In the finale The Goodbye Gossip Girl, Nate tells Vanessa and Dan that he plans to abandon his internship after the mayor took an interest in him. He asks her if they can go on their backpacking trip after all, and she agrees to let him come.
In the premiere Reversals of Fortune, Vanessa reveals to Dan that her and Nate hooked up one night in Prague while backpacking but nothing serious came from it. In The Grandfather: Part II, Nate's cousin Tripp allows Vanessa to film his campaign for Congress. On Election Day, Tripp is down in the polls and while taking a walk with Nate, he sees a man drowning in the Hudson River and saves him. Vanessa is the only one who filmed it, and agrees to sell the footage to New York 1. While reviewing the tapes, she realizes the man who was drowning purposely jumped in and faked the whole thing. She warns Nate to help him avoid a public scandal, but reveals she still plans to sell the footage. To prevent this from happening, he sets up a fake reporter to buy the footage. When she learns what he did, she gives it to the real network and the scandal comes out.
After Vanessa is framed for trying to get Serena van der Woodsen kicked out of Columbia by Nate's new girlfriend Juliet Sharp, she is iced out from everyone on the UES. However, after Nate learns that Juliet is a liar, he teams up with Vanessa to help expose her. He takes her out for coffee while Vanessa searches her apartment for anything suspicious, and she finds photos of Serena with her professor, Colin Forrester. Once Nate gets the truth, he calls their plan off but Vanessa keeps the memory card. At the ballet, she tells Nate she plans to inform the dean of Serena's affair and he begs her not to. But tired of losing to Serena constantly, she plans to do so anyway; although she ultimately fails to expose it (Juliet Doesn't Live Here Anymore).