Kate Mosley

Jennifer Aniston

Nick

Jay Mohr

Sam Mayfair

Kevin Bacon

Rita Mosley

Olympia Dukakis

Darcy O'Neil

Illeana Douglas

Darcy O'Neil

Kevin Dunn

Sela

Anne Twomey

Mrs. Mercer

Faith Prince

Jim Davenport

John Rothman

Mrs. Davenport

Margaret Gibson

Jackie Davenport

Meg Gibson

Brad

Paul Cassell

Ad Executive No. 1

Ivar Brogger

Ad Executive No. 2

Peter McRobbie

Ad Executive No. 3

Bray Poor

Ad Executive No. 4

Daryl Edwards

Ad Executive No. 5

Jenna Stern

Ad Agency Receptionist

Bellina Logan

Ad Agency Researcher

Sean Patrick Thomas

Pregnant Friend

Andrea Bendewald

Rosie

Marcia DeBonis

Darcy's Husband

Matthew Sussman

Anchor Person

Jim Ryan

Maitre D'

Doug Easley

Snack Lady

Ali Marsh

Watch Seller

Richard Spore

Susan

Amelia Campbell

The Maharishi

Vimesh Thakar

Sajit

Faran Tahir

Minister

David Cromwell

Bride

Jessica Cushman

Groom

Barry Del Sherman

Little Girl

Kaley Cuoco

Date #1 (uncredited)

Greg Grunberg

Ad Executive (uncredited)

Whit Washing

Glenn Gordon Caron

Carter Burwell

Molly Madden

Arleen Sorkin

Ed Barteski

Erwin Stoff

Paul Slansky

William Teitler

Tom Fleischman

Jonathan Gunning