Lily Blair is a theater student in the class of 2022.
While she has been a consistent star of the stage at Winter Lake Academy for the Arts, her real breakout is in "Songs from Down There," where she brings an earnest down-home early-Taylor-Swift charm to the ballad "My First Tampon Experience." She is approached for a record deal based on her performance and is forced to choose between her life-long dream of attending the Hartt School for musical theater and going to Hollywood where she knows nobody.
When she ultimately makes the decision to go to Hollywood, she hits a roadblock when her personal website is edited to make her look bad by a boy she turned down for a date after he helped set up the page. While Rocky gets to work helping Lily make things right on her site, the rest of the staff rallies around her and shares their own embarrassing moments for solidarity.