This film is part of the Cult Classic Collective strand at the Genesis Cinema.
Chicago Reader review:
This wicked little black comedy (2002), adapted from a short story by Mary Gaitskill, chronicles the perverse attraction between a young typist (Maggie Gyllenhaal) and her uptight boss (James Spader), a sadomasochistic tango that strikes unexpected chords in each character. The young woman is a self-mutilator, and when the attorney spanks her for a minor mistake, she knows she's found the right job. The film's romantic conceit turns on the decidedly un-PC notion of female submissiveness, but director Steven Shainberg (Hit Me) twists the story into a sly and stylized study of two lonely souls who come to realize they're made for each other. Spader is both haughty and tender as the sadistic control freak, and Gyllenhaal is even better as the love-starved kitten, crawling around on all fours and meowing for more. Angelo Badalamenti wrote the creepy score; with Lesley Ann Warren as the typist's overly solicitous mother and Stephen McHattie as her self-loathing father.
Here (and above) is the trailer.