Jennifer Aniston

Kate

Jay Mohr

Nick

Kevin Bacon

Sam

Olympia Dukakis

Rita

Illeana Douglas

Darcy

Kevin Dunn

Mr. Mercer

Anne Twomey

Sela

Faith Prince

Mrs. Mercer

John Rothman

Jim Davenport

Meg Gibson

Mrs. Davenport

Paul Cassell

Brad

Ivar Brogger

1st Ad Executive

Peter McRobbie

2nd Ad Executive

Bray Poor

3rd Ad Executive

Daryl Edwards

4th Ad Executive

Jenna Stern

5th Ad Executive

Bellina Logan

Ad Agency Receptionist

Sean Patrick Thomas

Ad Agency Researcher

Andrea Bendewald

Pregnant Friend

Marcia DeBonis

Rosie

Matthew Sussman

Darcy's Husband

Jim Ryan

Anchor Person

Doug Easley

Maitre D'

Ali Marsh

Snack Lady

Richard Spore

Watch Seller

Amelia Campbell

Susan

Vimesh Thakar

The Maharishi

Faran Tahir

Sajit

David Cromwell

Minister

Jessica Cushman

Bride

Barry Del Sherman

Groom

Kaley Cuoco

Little Girl

Greg Grunberg

Date #1 (uncredited)

Whit Washing

Ad Executive (uncredited)