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.
Meanwhile, Dan's mother Alison Humphrey has returned after having an affair in Hudson and only Vanessa knows the turmoil that's causing the family.
When she's not sleeping with her on-again-off-again boyfriend in the novels, Vanessa's taking morbid black-and-white photos and videos, shaving her head, assisting arrogant filmmaker Ken Mogul with his movies, or babysitting spoiled twins.Vanessa is horrified when Dan announces he is gay but remains a great friend to him, and it is her who realizes he isn't when they have sex again.After Nate brings by some of his old SAT study materials, Vanessa discovers a practice essay he wrote; detailing his struggle to choose between his parents and dealing with his father's embezzlement scandal and subsequent arrest.This leads Vanessa to apologize to him for ever judging him before getting to know him and they go to Vanessa's sister's concert to hang out.While filming, she catches Blair confessing sleeping with Chuck and then faking her virginity for Nate.
After being confronted by the two, she decides to give the tape to Blair to destroy (School Lies).
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.
When Serena broke his heart, however, Vanessa swooped in to pick up the pieces, and the two quickly embraced their love for each other.
Since both of them are tormented souls and aspiring artists, Vanessa feels they're meant to be together.
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.