John Cusack and Demi Moore star in this romantic comedy written and directed by Savage Steve Holland. Hoops McCann (Cusack) is no good at basketball, much to the disappointment of his family. He would rather study art and design and needs to write and illustrate a love story for his college application.

As Hoops searches for inspiration, he travels to Nantucket with his friends for the summer, picking up Cassandra Eldridge (Moore), a singer, on the way. She is fighting to save her grandfather's house from greedy property developers and Hoops and his friends cause mayhem as they attempt to help her. Can Hoops find time for love amidst the chaos of summer?