Diane Lane as Sarah

John Cusack as Jake

Elizabeth Perkins as Carol

Christopher Plummer as Bill

Dermot Mulroney as Bob

Stockard Channing as Dolly

Ali Hillis as Christine

Brad William Henke as Leo

Julie Gonzalo as June

Glenn Howerton as Michael

Ben Shenkman as Charlie

Jordana Spiro as Sherry

Kirk Trutner as Deli Guy

Victor Webster as Eric

Michael Spound as Marc

Will McCormack as Jason

Ted Griffin as Bill Jr.

Marylouise Burke as Aunt Eileen

Brad Hall as Stanley

Bobby Coleman as Austin

Emma Prescott as Molly

Jaden Sorensen as Justin

Will Rothhaar as Jeremy

Tony Bill as Walter

Patrick St. Esprit as Marshall

Josh Stamberg as Lennie

Anoush NeVart as Mrs. Parseghian

Krikor Satamian as Mr. Parseghian

Jon Lindstrom as Peter

Patrick Fabian as Donald

Steve Schirripa as Vinnie

Bess Wohl as Rebecca

Laura Kightlinger as Marcia

Rubria Negrao as Sonia

Colin Egglesfield as David

Suzy Nakamura as Mai

Jamie Denbo as Bertha

Miles Hull as Timmy

Amy Kidd as Jennifer

Ted Detwiler as Boat Guy

Kate McClafferty as Coxswain

Shana Hiatt as Hostess