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For Lee (Maggie Gyllenhaal), the young woman who will come to embody the job title from which Steven Shainberg’s Secretary (2002) gets its name, prospects of working provide her with a stability she craves beyond the financial. It was just the other day — on the afternoon of her sister’s wedding, to be precise — that she was released from a psychiatric facility. (Years of kept-secret self-harm had culminated in a suicide attempt.) Stewing at home afterward, where her trying-her-best mother (Lesley Ann Warren) puts on a brave face around an alcoholic, physically abusive husband (Stephen McHattie), only takes Lee back to the brink she hadn’t long ago climbed off. So when she gets a job as a secretary for a lawyer most people just call Grey (James Spader), it feels, to her, like a life raft coming in the form of a desk and typewriter. 

The comforting banalities of the job — her first — won’t last long. Grey’s impossibly high standards create the sort of hostile workplace where a single typo inspires a stormy lecture. Then it becomes something else entirely when an affair begins. Only it isn’t quite a vision of a typical workplace fling. Grey is very into S&M — which turns the typo thing into part of his and Lee’s play — and it’s suggested that his secretaries generally rotate in and out, made into a submissive teammate in his sex games until he abruptly decides he doesn’t want to play anymore. (The secretary preceding Lee is still packing up her things over shocked tears when her successor comes in for her interview.) Lee will not, Grey soon learns, be deterred the same way her predecessors have. It isn’t long before she’s invested everything not just into this job but into him, so rigid in her love that she will not budge until he’s willing to admit that he loves her back. 

I didn’t quite know what to make of Secretary in the moments just after watching it; I still don’t, really. But I knew I liked it — how its characters are damaged and strange but never turned into condescended-to grotesques, how it sees clearly the monstrousness inherent to a predatory boss who sexualizes his women employees but still hears out the perspective of a female lead who sees things differently. By the end of the movie, the pair, spoiler alert, has found a dynamic that works for them. 

Secretary is funny; it lives in a heightened world where outside Grey’s office sits a vacancy sign flashing whether he needs a new secretary, and where he has a button attached to his desk that spritzes the elaborate spread of orchids he rears a few feet away. But its funniness never undermines what’s serious about it, particularly Lee’s history of self-harm. Gyllenhaal, in her breakthrough performance, does great, open-book work; it’s touching to watch Lee, even if it’s easy to wish it were under different circumstances, get to a place in life where she feels like her needs are being met — where she feels like she’s being seen the way she’d like to be. 

Spader does a variation on the man-with-an-unorthodox-relationship-to-sex routine previously seen in sex, lies, and videotape (1989), Dreamlover (1993), and Crash (1996), though it’s arguably here that he’s the most conflicted about said unorthodox relationship. Later in the film, he’ll wonder unhappily why he’s drawn to this specific secretarial kink and the interplay therein. Secretary is an oddball romance where he’ll find a woman who helps him live without shame, and vice versa.