Fifteen-year-old Robert Hunt is confused after playing Shakespeare's Rosalind in a skit for English class. He liked dressing as a woman and he's good at it. It gives him a confidence that spills into his regular persona as Rob, allowing him to finally go out on a date with Milena.

They attend a gender-bending party, where he discovers that Milena likes dressing up as a guy and his best friend Kevin comes out of the closet.

Robert begins to doubt his new personality after his father learns of his cross-dressing. But he enjoys being Rosalind; how can that be wrong? When he begins to lose sight of who Rob is, he finds that there is a place for all the sides of his personality.

Readers will see that people do not necessarily fit under just one label; rather, they have many layers, or sides. While THE FLIP SIDE does a good job at illustrating the gray sides in everyone, the ending comes almost too quickly and neatly to be entirely believable, leaving readers with a few questions.