Maggie Gyllenhaal

Lee Holloway

Julene Renee

Jessica

Ezra Buzzington

Typing Teacher

Lesley Ann Warren

Joan Holloway

James Spader

Mr. Grey

Stephen McHattie

Burt Holloway

Jeremy Davies

Peter

Herbert Russell

Second Date

Patrick Bauchau

Dr. Twardon

Osgood Perkins

Jonathan

Jessica Tuck

Tricia O'Connor

Amy Locane

Lee's Sister

Mary Joy

Sylvia

Michael Mantell

Stewart

Lily Knight

Paralegal

Sabrina Grdevich

Allison

Lacey Kohl

Louisa

Lauren Cohn

First Secretary

Kyle Colerider-Krugh

Mr. Garvey

Steven Fierberg

First Date

David Wiater

Tomato Date

Shannon Convery

New Secretary

Alison Tatlock

TV Reporter

Christina Gray

Photographer (uncredited)

Steven Shainberg

Director

Joel Posner

Executive Producer

Michael Roban

Executive Producer

P.J. Posner

Executive Producer

Jamie Beardsley

Executive Producer