Tomboy to the core, Toni Valentine understands guys. She'll take horror movies, monster hunts and burping contests over manicures. So Toni is horrified when she's sent to the Winston Academy for Girls, where she has to wear a skirt and learn to be a "lady" while the guys move on without her. Then Toni meets Emma Elizabeth, a girl at school with boy troubles, and she volunteers one of her friends as a pretend date. Word spreads of Toni's connections with boys, and she discovers that her new wealthy female classmates will pay big money for fake dates. Looking for a way to connect her old best friends with her new life at school, Toni and Emma start up Toni Valentine's Rent-A-Gent Service. But the business meets a scandal when Toni falls for one of her friends--the same guy who happens to be the most sought-after date. With everything she's built on the line, Toni has to decide if she wants to save the business and her old life, or let go of being one of the guys for a chance at love.