Secretary opens on a young, pretty receptionist named Lee Holloway (Maggie Gyllenhaal). As Lee gracefully prepares coffee and gathers papers, one can see she is both good at and proud of her run-of-the-mill reception job. It also happens that Lee is doing all of her work in a bondage rig — arms outstretched and immobile, hands manacled to a bar with cuffs at each end.
The end of her routine brings her to a dark, stately office. Lee stares out from the private room, her gaze almost cold. She seems to pose for a moment, her hip confidently cocked, before swinging the door shut with her foot. We are not yet welcome into her private sanctum, her inner workings. Thus, Secretary begins with a gaze of defiance from a confident, composed, and kinky young woman.
It’s almost startling to see Lee in a flashback scene moments later. Only a few weeks earlier, we see that the self-assured young woman from the beginning of the film is living in an insecure body — slouched in on herself, dressed in a frumpy cardigan and ill-fitting socks, speaking with a sort of adolescent, unsure tone that permeates her mannerisms.
Released in 2002, directed by Steven Shainberg with a screenplay by Erin Cressida Wilson based on a story by Mary Gaitskill, Secretary follows this character Lee Holloway, a young woman with severe self-harm issues who seems trapped in a state of arrested development. Yet when Lee begins a sadomasochistic relationship with her boss, the stern and strange lawyer Edward E. Gray (James Spader), she is freed from her own punitive mind, and finally finds a sense of purpose and self.
Made prior to our current cultural era of hyper-specific labeling of womanhood — before the endless picking-apart and narrativizing of “Fleabag eras,” dissociative feminism, and the reclaiming of words like “slut” and “bimbo” — Secretary just lets itself be what it is. Secretary doesn’t feel like it’s trying to change the world, normalize anything, or make some grand social point. Instead, it allows for itself to be ethically sticky for the sake of sexy fantasy. Secretary feels special and intimate, a gift of a film for pervy, daydreamy, masochist girls everywhere.
Our protagonist, Lee Holloway, is equal parts sweet and off-putting. At the beginning of the film, Lee mourns her stint at a mental institution ending because she so adored its forceful routine. She chews her nails and her hair, and none of her clothes really fit right. She’s twenty-something years old and taking baths with a little snow globe fairy next to the tub, but she’s also sneaking cigarettes before bed and stealing her family’s hot kettle to scald her own thighs with.
Her new boss, Edward Grey, is equal parts seductively stern and strange. He’s hard to read and inappropriate from his and Lee’s very first meeting, where he grills her inexplicably about her home life. At moments he’s doting and tender (“Are you shy?” he coos to her gently on his office couch at one point early on in his seductions, as Lee blushes and squirms, before assuring her he wants to help her), and at others he’s dismissive and cruel, tearing apart everything about Lee from her work ethic to her appearance, or making her go through the dumpster (which, it’s important to note, Lee does with an almost puppy-like eagerness) when he “accidentally” throws out important papers.
The two are a match made in BDSM heaven, as Mr. Grey’s pleasure in dressing-down Lee and insisting that she performs acts of subservience end up giving Lee a sense of purpose and paradoxically empower her. This flirtatious, slippery play eventually devolves into an actual spanking over one of Lee’s typing errors, which acts as the final catalyst for their full-fledged BDSM dynamic to blossom.
Edward and Lee’s play gradually becomes sexual, but in small and orgasmic fits and starts. Lee daydreams of her boss in her bed as she falls asleep. Mr. Grey masturbates onto the back of her dress shirt, which in turn makes Lee excuse herself to the bathroom and masturbate in the stall. They’re turning each other on, and willing to act on it, yet so much is unspoken. At most, their fingers gently brush after a spanking. At most, Edward tells Lee that her typed letter is finally “good.” Only at the very last moment does their relationship become romantic, but this tension makes their dynamic all the more dizzying.
For Lee and Edward, sadomasochistic play seems to transcend some sort of sexual superficiality. It is inherent to their very spirits, it allows them to make sense of who they truly are. You can almost see Lee becoming spiritually freed in the pink flush of her face, as Edward Grey cooly tells her over the phone that she is permitted exactly four peas for dinner.
To dismiss Secretary’s relationship as something that’s simply smutty or sexy is to not understand it. What makes Secretary so wonderful is its full embracing of fantasy. The film dreamily suggests that Lee can be healed of a lifelong compulsion toward self-harm because her handsome and strange boss likes to spank her during lunch hour. (The New York Times’ review of the film describes Lee as “[blooming] under the spanking hand of her boss”).
This premise is, of course, a little ridiculous. But aside from the sadomasochistic context it sits within, is Lee’s being swept off her feet not ultimately just an alternative iteration of the fantasy romantic comedies feed us? The notion that a man can step in and save you and you will suddenly be freed of the weight of existing, and instead will be able to live free and easy and out of your own head?
And as for the kinky interactions actually presented — they often feel almost coy, tongue-in-cheek. Where a romcom’s usual whirlwind montage of dates would be placed, in this film we instead see Lee and Mr. Grey diving into a montage of playful presentations of BDSM ranging from Lee nibbling food out of her boss’ hand to donning a horse saddle on a bed of hay to crawling about on the floor with stationary in her mouth. It’s both perverse and silly.
With twenty years behind it now, Secretary could, in many senses, be seen as a harbinger for a handful of pop culture crazes to come. It feels like a striking coincidence, if it is one at all, that the Fifty Shades of Grey film franchise’s sadist has the same last name as the lawyer in Secretary. In fact, some modernized marketing for Secretary that followed on the heels of the craze of Fifty Shades coyly calls Edward E. Grey “the original Mr. Grey.” That said, even in 2002, the world seemed ready for this kinky premise; Maggie Gylenhaal recalls her plans to defend the film against a wave of conservative criticism that never really came. It seems even twenty years ago that people were quite pleased with what Secretary had to offer, and seemed understanding of its fantasy-like nature.
Beyond the film’s direct ties to representation of kink and BDSM in art, Secretary also seemed like an early entry into the millennial dissociative feminism fantasies of a life where someone else handles your decisions for you — a theme that currently artistically en vogue. Masochist girls partaking in ethically sticky situations are now a labeled aspect of the zeitgeist, easily found in characters like Normal People’s Marianne (Daisy Edgar Jones) and her endless insistence that she would do whatever to make her partner Connell (Paul Mescal) happy, or Fleabag’s titular character and her iconic pleading with The Priest (Andrew Scott) to help her find someone who will tell her what to do forevermore, down to what she eats, wears, watches, and listens to.
While a sense of cultural foreshadowing can certainly be plucked from Secretary, the film honestly continues to feel like its own special, weird little slice of cinema, as if it hovers above the discourse. (In fact, the only cultural touchstone I would argue that has a direct correlation to Secretary is the Christmas-special episode of The Office “Christmas Wishes” where an older James Spader, playing the strange and aloof CEO Robert California, coerces the people-pleasing, ditzy office secretary, Erin (Ellie Kemper) into letting loose for a night with a sort of cooing but stern speech that feels ripped almost directly from Secretary. I cannot imagine this is an accident).
It takes a long while for Secretary to become a love story at all. For the vast majority of the film, it’s a crush story, it’s a coming-of-adulthood story, it’s a burgeoning sexuality story, and it’s also something beyond all that. The interactions between Lee and her sometimes pushy, sometimes cold, and sometimes doting boss are slippery and hard-to-define, even before he begins spanking her for her spelling errors.
Secretary feels like its own special, magical cinematic space, almost pure in intention. It is silly when you least expect it, sexy when you don’t think it will be, and tender when you need it most.
Much like the film opens with a look of defiance, it ends with one, too. After completing the final test for Mr. Grey— a day and night spent without food or water, sitting at Mr. Grey’s desk in a wedding dress and not permitted to move until he returns — Lee finally gets the guy. They marry (at a courthouse, in a black dress, and then rush to go have some freaky, bondage-y sex out in the wilderness), and begin life in an unassuming house in a Florida cul-de-sac, creating an insular and kinky world where Lee stays at home with the pillows fluffed just right and the sheets tucked carefully.
Moments after waving goodbye to Edward for the day from their little front porch, Lee turns to look directly at the camera. Her pretty and parted lips press into a thin, challenging line. Her head cocks slightly. She is daring us to pass judgment, to sneeringly accuse her of failing to find happiness through conventional means.
This moment is striking, and borders on beautiful. Lee’s final defiant gaze posits that Secretary is a fantasy of finding salvation through something that is all your own, even if that salvation is found in spankings and the occasional constructed berating. You may not understand it, but that’s irrelevant to Lee and her happy, freaky little life.
