Two college friends, now in their thirties, admire each others' lives and feel trapped in their own. Wes, tied to a demanding career and responsibilities to family, extends a work trip to drag his dispirited artist friend Luke to find Luke's "one that got away."
A woman who is robbed on her way to catch the 1:30 train to Boston is left stranded in New York City. She meets a man who helps her during the course of the night and the two form a romance.
Emma is spiraling out of control amidst the crazy abyss of Hollywood nightlife. After her latest night of regret, she finds herself waking up in the morning to yet another drunk disaster of a man. That same afternoon, she decides she is going to check in on her ex-boyfriend that evening. While figuring out what to wear, Emma shuffles through all of her clothes in her closet. Each outfit brings her back to a specific memory of her promiscuous past. Finally, she reconnects with her ex and they share an unexpected moment. Leading her to further evaluate her current disposition.
Unless Darren can survive New York's largest drug mogul, write a paper on Dante's "Inferno," escape three thugs chasing the wrong guy and sell fifty pills of ecstasy to make his tuition payment, he'll never date the girl of his dreams.
On a bet, a gridiron hero at John Hughes High School sets out to turn a bespectacled plain Jane into a beautiful and popular prom queen in this outrageous send-up of the teen movies of the 1980s and '90s.