If Lucy Fell (1996)

A comedy for the romantically challenged.

Cast

Sarah Jessica Parker, Eric Schaeffer, Ben Stiller, Elle Macpherson, James Rebhorn

Overview

Joe and Lucy are roommates and best friends. Lucy, whose love life is embarrassingly dull, convinces Joe, who is infatuated with a neighbor he's never met, that if they don't have stable romances within a month, they must jump off the Brooklyn Bridge.