How many of you have thought how great it would be to go back to high school with everything you know now? Everyone. And why? Because then you wouldn't make the same ridiculous mistakes as you did. But, unfortunately, you can't redo the past or go back to the high school, because the real life stirs you into a different direction. This story revolves around Josie Gellar (Drew Barrymore), who is actually 25 and is working for Chicago Sun Times as a copy editor. Now, she gets a chance to enrol into her high school again as an undercover news reporter. But, as she was a total nerd as she was in high school, she doesn't actually know how to be popular ad get the story she needs. That is where her naturally funny brother Rob comes in the action. He gives her total makeover and teaches her how to be popular. Also, he manages to spread lots of rumours about her, telling everyone that she dated a drummer from a famous rock band, that she is a wild child in heart and things like that. But, as they get to party all the time, like back in the days, she also falls in love with one of her teachers- Sam Coulson (Michael Vartan). And with the publication deadline approaching really fast, she must do something or she will lose one of these things- her cover up, her job, or the guy she is falling for.