As if having a younger sibling that's cooler than you isn't already embarrassing enough, Rob is the type who rubs his popularity in everyone's face, even when he's trying to help. He eventually helps his sister Josie (Drew Barrymore), a reporter who's trying to expose the secret lives of teenagers by going undercover as a high school student, get in with the cool kids—after he re-enrolls with her and effortlessly achieves popularity first.