Sandra Bullock as Lucy Kelson

Hugh Grant as George Wade

Dana Ivey as Ruth Kelson

Robert Klein as Larry Kelson

Alicia Witt as June Carter

Heather Burns as Meryl Brooks

David Haig as Howard Wade

Dorian Missick as Tony

Joseph Badalucco Jr. as Construction Foreman

Jonathan Dokuchitz as Tom

Veanne Cox as Melanie Corman

Janine LaManna as Elaine Cominsky

Iraida Polanco as Rosario

Charlotte Maier as Helen Wade

Katheryn Winnick as Tiffany

Jason Antoon as Norman

Rocco Musacchia as Fisherman

Wynter Kullman as Tyler

Francie Swift as Lauren Wade

Adam Grupper as Ex-Mrs. Wade's Lawyer

Johnny Dee as Homeless Man

John Cunningham as Justice of the Peace

Mark Feuerstein as Rich Beck

David Aaron Baker as Man Getting into Cab

Teagle F. Bougere as Willie the Bellboy

Mandy Siegfried as Hana the Hostess

Mark Zeisler as Mr. Lowell

Nadine Mozon as Ms. Gonzales

Tim Kang as Paul the Attorney

Libby West as Masseuse

Sharon Wilkins as Polly St. Clair

Mike Piazza as Mike Piazza

Shannon Fiedler as Cookie Girl

Becky Ann Baker as RV Woman

Adam LeFevre as RV Man

Sebastian Rand as RV Son

George Gearhart King III as RV Son

Donald Trump as Donald Trump

Norah Jones as Norah Jones

Bill Bowers as Dance Floor Mime

William Thourlby as Man in Elevator

Elizabeth Owens as Woman in Elevator

Dori Kancher as Farewell Party Girl

Marina Lutz as Lucy's Assistant

José Ramón Rosario as Assemblyman Perez

Craig 'Radio Man' Castaldo as Radioman (uncredited)