Jennifer Aniston as Kate

Jay Mohr as Nick

Kevin Bacon as Sam

Olympia Dukakis as Rita

Illeana Douglas as Darcy

Kevin Dunn as Mr. Mercer

Anne Twomey as Sela

Faith Prince as Mrs. Mercer

John Rothman as Jim Davenport

Meg Gibson as Mrs. Davenport

Paul Cassell as Brad

Ivar Brogger as 1st Ad Executive

Peter McRobbie as 2nd Ad Executive

Bray Poor as 3rd Ad Executive

Daryl Edwards as 4th Ad Executive

Jenna Stern as 5th Ad Executive

Bellina Logan as Ad Agency Receptionist

Sean Patrick Thomas as Ad Agency Researcher

Andrea Bendewald as Pregnant Friend

Marcia DeBonis as Rosie

Matthew Sussman as Darcy's Husband

Jim Ryan as Anchor Person

Doug Easley as Maitre D'

Ali Marsh as Snack Lady

Richard Spore as Watch Seller

Amelia Campbell as Susan

Vimesh Thakar as The Maharishi

Faran Tahir as Sajit

David Cromwell as Minister

Jessica Cushman as Bride

Barry Del Sherman as Groom

Kaley Cuoco as Little Girl

Greg Grunberg as Date #1 (uncredited)