'Casanova, Baby!' follows the story of a high school boy, Zack, whose friend Kyle is bugging him at lunch about his crush on the new girl, Zooey. As Kyle prods Zack to ask Zooey out, Zack pushes this encouragement away because he doesn't know how to ask her out. He falls into various daydreams of how his wooing of Zooey could play out. These daydreams are inter-cut with his conversation with Kyle and brings us to the end of the day and Zack has let Zooey get away without a word.