The only issue? Josie didn’t exactly have the strongest social game as a teen the first time around. And while she totally has been kissed, she’s the type of hopeless romantic that believes she should only be puckering up for “the person you’re supposed to kiss for the rest of your life.”

Basically, she’s totally going to kill it with her fellow youths.

Dressed in an unfortunate all-white ensemble, Josie quickly befriends brainy Aldys (Leelee Sobieski), an aspiring professor, novelist and flautist who has already figured out that her best years lie ahead, and develops a troubling crush on Cool Teacher Sam Coulson (Michael Vartan).

But with prom fast approaching, hanging with the math club (appropriately named the Denominators) and lusting over an English instructor with boundary issues is not going to get Josie the cover story she’s after.

For that she relies on brother Rob (David Arquette), also going undercover, to gain her entrée into the cool kids group, which includes a pre-stardom James Franco and Jessica Alba.