Natalie writes the relationship column for her high school newspaper. Then she is accused of knowing nothing about guys and giving girls bad relationship advice, so she decides to disguise herself as a guy and spend a week at Underwood Academy, the private all-boys boarding school in town. And in the process, she learns about guys, though in ways she never expected. But when she starts to fall for her dreamy roommate, things get even more complicated. The fun doesn't stop in this light, lively offering for teen girls.