Willa makes her first appearance in The Last Days of Disco Stick, when Blair expresses interest in joining the Tisch program. Leader Paul Hoffman explains to everyone that he is planning to have a fairy tale themed cabaret, which he unfortunately cannot get Lady GaGa to attend. When Blair offers the help of her stepfather, entertainment lawyer Cyrus Rose, Paul brushes her off and mentions that Willa's father is Harvey Weinstein. During the cabaret, Willa plays the role of Little Red Riding Hood.
In The Debarted, Willa invites Dan to come with her, Vanessa, and Paul to her country house. He initially says no, but changes his mind after Nate Archibald encourages him to go. She asks Dan to meet her at her dorm before they leave and when he does, he finds her eager to show him an art performance piece of hers. They watch it, and it ends up being a video of herself naked and breathing heavily. They end up making out but nothing else happens, due to Dan stopping and admitting he can't because of his own issues. At the end of Inglourious Bassterds, Willa brings Vanessa a letter from Tisch, and adds that she didn't know she was applying for the playwriting program. Vanessa replies that she's not really telling anyone and Willa wishes her luck.
In Dr. Estrangeloved, Dan admits to Willa to Vanessa only got accepted into the Tisch program because she submitted a screenplay based off one he already wrote. Knowing that submissions have to be original, Willa calls her father to tell him about what Vanessa did. Later, Dan discovers that the piece Vanessa submitted was actually an original and he tried to contact Willa to get her to undo telling her father. He eventually finds her at an art party at Brooklyn, where she explains that she turned her phone off to get into the art zone. He asks her to fix things for Vanessa but she refuses, saying that he deserves to be at Tisch more than Vanessa before trying to kiss him. Startled, he informs her that he's with Vanessa and the notices that Jenny Humphrey is at the party. She says hi to Dan before walking away and Willa rudely asks who that slut is. Dan annoyedly tells her to call her father and walks away. Offended by this, Willa later tells Vanessa about the whole thing. This is Willa's last appearance in the show.