Edit In School Lies , Vanessa films Dan for a documentary she's making to enter in a contest, hoping to win some prize money. Once Dan and Vanessa arrive, they witness an accident in which a boy almost drowns. While everyone is hurrying to leave, Vanessa catches a shot of Chuck holding the pool key used for entry. After the students are given an essay to write as punishment, Blair Waldorf invites everyone to her penthouse so they can work together.
During the study party, Vanessa shares with Dan that Chuck was the one who initiated the party. However, once confronted about it, Chuck denies doing so and says he only took the key so everyone didn't get blamed.
Meanwhile, Vanessa catches footage of a conversation between Blair and Chuck; in which Blair admits she faked her virginity for her boyfriend, Nate Archibald , to cover up that she slept with Chuck first. Once both realize she was filming, they demand that she hand over the tape but she decides to keep it. The next day, Blair tries to manipulate Vanessa into giving her the tape but fails. Later that day, Vanessa gives the real tape to Blair, explaining that the tape she gave Chuck was a blank one.
As a result, Blair pays Vanessa's rent for a month and Vanessa tells her that she used the money from Chuck to create a medical grant for teens with genital herpes in his name. She realizes that her only real chance is to blackmail Blair into helping her, by threatening to expose that her ex, Marcus Beaton , was two timing her with his stepmother, Catherine.
Not wanting to be bested by Vanessa, Blair makes a deal with Chuck for him to seduce and humiliate her as revenge. Chuck initially agrees, bribed by Blair offering herself in exchange, but becomes serious about saving the bar once he visits it and meets the owner, a kind elderly man named Horace Rogers.
Vanessa is impressed when she realizes that Chuck's business proposal includes keeping the bar as is, and accepts when he invites her to a housewarming party at the Van der Woodsen penthouse that night.
At the party, Chuck is told by his father, Bart Bass , that he will not approve Chuck's purchase and that he's disappointed but not surprised at his letting people down. Vanessa overhears the conversation and later tries to comfort Chuck, but he agrees that he is exactly what Bart said he was.
Meanwhile, Blair notices that Chuck and Vanessa are getting closer and calls off their deal, citing boredom. She is also able to delete Vanessa's blackmail off her phone, freeing her from any potential problems in the future. Before the end of the night, she confronts Vanessa to reveal her deal with Chuck, saying that the real estate deal was foreplay and humiliating her was the real goal.
Chuck doesn't deny it, and Vanessa realizes she was used. On Jenny Humphrey 's birthday, Vanessa becomes increasingly concerned over Nate's newly found friendship with his ex, Blair. While visiting Dan, she receives an email from Nate asking her to meet him at his house.
Once she arrives, she finds Chuck instead; who explains that he knows Nate's email password and sent her the email to lure her over in time to see Blair leaving his house, which she does every morning. She brushes this off until Nate actually dumps her, saying it's because things have reached a natural end, not because of Blair.
Knowing he's lying, Vanessa decides to go to Chuck to get revenge. In order to peak their jealousy, Vanessa kisses Chuck in front of everyone. However, Vanessa is unsure if her efforts worked until she sees Blair leave the party without Nate.
The next day, it's revealed that she and Chuck slept together Remains of the J.