Madonna as Abbie Reynolds

Rupert Everett as Robert Whittaker

Benjamin Bratt as Ben Cooper

Malcolm Stumpf as Sam

Josef Sommer as Richard Whittaker

Suzanne Krull as Annabel

Linda Larkin as Kelly

Illeana Douglas as Elizabeth Ryder

Michael Vartan as Kevin Lasater

Lynn Redgrave as Helen Whittaker

Neil Patrick Harris as David

Mark Valley as Cardiologist

Stacy Edwards as Finn

John Carroll Lynch as Abbie's Lawyer

Fran Bennett as Judge Tracey Bennett

Ricki Lopez as Angel

Tiffany Paulsen as Young Mother

Jack Betts as Vernon

Irene Roseen as Lena

Caitlin Wachs as Rachel

Jessica Sara as Kid #3

Kimberley Davies as Hostess

Laurent Schwaar as Restaurant Manager

Rebekah Hoyle as Orderly (uncredited)

Greg Bronson as Pedestrian (uncredited)

Colton Ford as Glen

Lee Lucas as Party Guest #2

Frank James as Dad at Airport

Benjamin Koldyke as Kelly's Boyfriend