Sarah Jessica Parker portrays Lucy Ackerman, a 29-year-old artist who makes a pact with her roommate to jump off the Brooklyn Bridge if they don't find love by the end of the month.
Eric Schaeffer plays Joe MacGonaughgill, Lucy's platonic best friend and roommate who agrees to the pact to jump off the Brooklyn Bridge if they remain single.
Ben Stiller takes on the role of Bwick Elias, a neighbor of Lucy and Joe who is an artist and loves to cook.
Elle Macpherson portrays Jane Lindquist, an attractive and confident woman who catches the eye of Lucy's friend Joe.
James Rebhorn plays Simon Ackerman, Lucy's father who offers her some advice about life and love.
Robert John Burke appears as the Handsome Man, a character who encounters Lucy in an elevator.
Scarlett Johansson has a role as Emily, Lucy's sister who visits her in New York City.
Dominic Chianese portrays Al, a wise and supportive friend of Lucy and Joe.
Emily Hart plays Eddy, another friend in Lucy and Joe's circle who joins in their adventures.
David Thornton portrays Ted, a friend of Lucy and Joe who has his own struggles with relationships.
Michael Storms appears as Sam, another friend in Lucy and Joe's social circle.
Jason Myers has a role as Billy, one of the friends who gets involved in Lucy and Joe's pact.
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