James Spader as Mr. Grey

Maggie Gyllenhaal as Lee Holloway

Jeremy Davies as Peter

Lesley Ann Warren as Joan Holloway

Stephen McHattie as Burt Holloway

Patrick Bauchau as Dr. Twardon

Jessica Tuck as Tricia O'Connor

Osgood Perkins as Jonathan

Amy Locane as Lee's Sister

Mary Joy as Sylvia

Michael Mantell as Stewart

Lily Knight as Paralegal

Sabrina Grdevich as Allison

Lacey Kohl as Louisa

Julene Renee as Jessica

Lauren Cohn as First Secretary

Ezra Buzzington as Typing Teacher

Kyle Colerider-Krugh as Mr. Garvey

Steven Fierberg as First Date

Herbert Russell as Second Date

David Wiater as Tomato Date

Shannon Convery as New Secretary

Alison Tatlock as TV Reporter

Christina Gray as Photographer (uncredited)

Cali T. Rossen as Dancing Party Guest (uncredited)

Diane McGee as Woman in the Purple Boots (uncredited)

Steven Shainberg as Richard Arevalos (Sex Therapist on Tape) (voice) (uncredited)

Erin Cressida Wilson as Sitting In Mr. Grey's Waiting Room (uncredited)