E. Edward Grey

James Spader

Lee Holloway

Maggie Gyllenhaal

Peter

Jeremy Davies

Joan Holloway

Lesley Ann Warren

Dr. Twardon

Patrick Bauchau

Burt Holloway

Stephen McHattie

Jonathan

Oz Perkins

Tricia O'Connor

Jessica Tuck

Lee's Sister

Amy Locane

Sylvia

Mary Joy

Stewart

Michael Mantell

Allison

Sabrina Grdevich

Paralegal

Lily Knight

Louisa

Lacey Kohl

Jessica

Julene Renee

First Secretary

Lauren Cohn

Paralegal Secretary

Mary Knight

Photografer

Christina Gray

Typing Teacher

Ezra Buzzington

Dancing Party Guest

Cali T. Rossen

Mr. Garvey

Kyle Colerider-Krugh

First Date

Steven Fierberg

Second Date

Herbert Russell

Second Date

Russell Harper

Tomato Date

David Wiater

New Secretary

Shannon Convery

TV Reporter

Alison Tatlock

Woman in the Purple Boots (uncredited)

Diane McGee

Richard Arevalos (Sex Therapist on Tape) (voice) (uncredited)

Steven Shainberg

Sitting In Mr. Grey's Waiting Room (uncredited)

Erin Cressida Wilson