Lee Holloway (Maggie Gyllenhaal) is a socially awkward and emotionally fragile young woman who has just been released from a mental health facility following an episode of severe self-harm, a coping mechanism she uses to numb her internal emotional pain.
Living back with her dysfunctional parents (Lesley Ann Warren and Stephen McHattie) and engaging in a dull, unfulfilling relationship with her childhood acquaintance, Peter (Jeremy Davies), Lee tries to find some normality by learning to type.
She is hired as a secretary for the eccentric, rigid, and intensely private attorney E. Edward Grey (James Spader) and finds that his stern, highly critical demeanour unexpectedly arouses her.
Over time, their professional dynamic evolves into an organic, consensual BDSM dominant-submissive relationship, with the obsessive-compulsive Grey doling out ritual punishments (such as spanking) for spelling errors and typing mistakes.
The role-play and structured discipline provide a therapeutic outlet for Lee, helping her channel her internal pain and heal from her emotional issues.
Despite Grey’s initial fears and insecurities about his own unconventional urges, Lee’s public displays of absolute devotion eventually bridge the gap, leading to genuine intimacy, mutual self-acceptance, and marriage.
Mr E. Edward Grey
James Spader Lee Holloway
Maggie Gyllenhaal Peter
Jeremy Davies Joan Holloway
Lesley Ann Warren Burt Holloway
Stephen McHattie Dr Twardon
Patrick Bauchau Tricia O’Connor
Jessica Tuck Jonathan
Osgood Perkins Lee’s Sister
Amy Locane Sylvia
Mary Joy Stewart
Michael Mantell Paralegal
Lily Knight Allison
Sabrina Grdevich Louisa
Lacey Kohl Jessica
Julene Renee First Secretary
Lauren Cohn Typing Teacher
Ezra Buzzington Mr Garvey
Kyle Colerider-Krugh First Date
Steven Fierberg Second Date
Herbert Russell Tomato Date
David Wiater New Secretary
Shannon Convery
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Living back with her dysfunctional parents (Lesley Ann Warren and Stephen McHattie) and engaging in a dull, unfulfilling relationship with her childhood acquaintance, Peter (Jeremy Davies), Lee tries to find some normality by learning to type.
She is hired as a secretary for the eccentric, rigid, and intensely private attorney E. Edward Grey (James Spader) and finds that his stern, highly critical demeanour unexpectedly arouses her.
