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The narrative unfolds as a timid young man, Cal, arrives for a date at the penthouse of June whose house resembles a whimsical modern art installation almost like Pee-Wee's Playhouse. He offers her roses, only to have them immediately rejected. What follows is a series of absurd, slapstick-inspired events—breaking a decorative bust, accidentally putting a fish in the June’s drink—that culminate in Cal posing shirtless on her indoor “beach” set, sparking June's creative epiphany and leading her to photograph him for a Vogue ad campaign. This short film was created in 1987 under the mentorship of Martin Scorsese while Gruber was a student at Columbia Film School, and has since earned a place in exhibitions at New York’s MoMA, cementing its status as a noteworthy artistic work.

David Piper has always been an outsider. His parents think he's gay. The school bully thinks he's a freak. Only his two best friends know the real truth: David wants to be a girl. On the first day at his new school, Leo Denton has one goal: to be invisible. Attracting the attention of the most beautiful girl in his class is definitely not part of that plan. When Leo stands up for David in a fight, an unlikely friendship forms. But things are about to get messy. Because at Eden Park School secrets have a funny habit of not staying secret for long, and soon everyone knows that Leo used to be a girl. As David prepares to come out to his family and transition into life as a girl and Leo wrestles with figuring out how to deal with people who try to define him through his history, they find in each other the friendship and support they need to navigate life as transgender teens as well as the courage to decide for themselves what normal really means.