Loser.

About Loser

Loser is a 2000 American teen romantic comedy film written and directed by Amy Heckerling. Starring Jason Biggs, Mena Suvari and Greg Kinnear, it is about a fish-out-of-water college student (Biggs) who falls for a classmate (Suvari), unaware she is in a relationship with their English teacher (Kinnear). The film, Heckerling's first after 1995's Clueless and inspired by the 1960 film The Apartment, was a box-office failure and received negative reviews.