Christina Ricci as Carolyn McDuffy

Hank Harris as Pumpkin Romanoff

Brenda Blethyn as Judy Romanoff

Dominique Swain as Jeanine Kryszinsky

Marisa Coughlan as Julie Thurber

Sam Ball as Kent Woodlands

Harry Lennix as Robert Meary (Poetry teacher)

Nina Foch as Betsy Collander

Caroline Aaron as Claudia Prinsinger

Lisa Banes as Chippy McDuffy

Julio Oscar Mechoso as Dr. Frederico Cruz

Phil Reeves as Burt Wohlfert

Marisa Petroro as Courtney Burke

Tait Smith as Hansie Prinsinger

Michael Bacall as Casey Whitner

Erinn Bartlett as Corinne

Michelle Krusiec as Anne Chung

Melissa McCarthy as Cici Pinkus

Amy Adams as Alex

Ginny Schreiber as Diana

Shaun Weiss as Randy Suskind

Julia Vera as Ramona Ramirez

Shane Johnson as Jeremy

Elsie Escobar as Sascha Santiago

Margaret Travolta as Vera Whitner

Beverly Lynne as Sorority Sister (uncredited)

John Henry Binder as Newscaster

Job Alonso as Disabled Soccer Player (uncredited)

Paul Michael Bloodgood as Tennis Fan (uncredited)

Lawrence R. Coddens as Customer (uncredited)

David Gibbs as Todd Ridgeway (Kent's Opponent) (uncredited)

Eric Marcel Jones as College Student (uncredited)