As her college valedictorian, Lelaina Pierce (Winona Ryder) should be destined for greatness. In reality she is a lowly production assistant for an obnoxious TV morning show (John Mahoney). In her free time, Lelaina is making a biting, often outrageous video documentary about her peers: (Steve Zahn) and her best friend Troy (Ethan Hawke), a brilliant but unmotivated rebel. Meanwhile, Lelaina meets Michael (Ben Stiller), an ambitious video executive who wants to showcase her documentary on "In Your Face TV". Suddenly, she finds herself at the centre of a very odd love triangle with dependable, fast-track Michael on the one side and a sexy, brooding Troy on the other.