Secretary

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

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David Wiater

as Tomato Date

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Shannon Convery

as New Secretary

Alison Tatlock

as TV Reporter

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Christina Gray

as Photographer (uncredited)

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Cali T. Rossen

as Dancing Party Guest (uncredited)

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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)