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Devotion Through Dysfunction: Secretary

Secretary is one of my favourite films of all time. And no, not because of its kinkiness or because it’s cool to like it. No, Secretary had a truly profound effect on me. Of course, I watched it because I’d heard it was kinky and cool, but something else happened. There, on the screen, was a woman just like me. Lee Holloway, with all her quirks and oddities, made me feel ok to be me; with all my quirks and oddities.

A fairly controversial film at the time of its release in 2002, Secretary is a romantic comedy in the way that Donnie Darko is a teen movie, or Fight Club is a buddy film. Many viewers will totally miss the point of the movie, and be up in arms about the imbalance of power between the lead male and lead female character, even though the imbalance is entirely an illusion and part of their thrill. Some people may fail to appreciate the passion, humour, and unorthodox eroticism of a film about a most unusual relationship, which would be a real shame as I truly believe that this is one of the most beautiful love stories ever told.

It begins when a complicated but unassuming young woman (Maggie Gyllenhaal) takes a secretarial position with the perplexing Mr. E. Edward Grey (James Spader). As the film basks in the luxuriant atmosphere of the law offices and Lee and Mr. Grey inch closer to each other, we gradually learn who they are.

Even those not partial to the appetites portrayed in the film may find it sexy because Secretary is not a movie about fetishism. It is a movie about intense passion. It is also a tease. A patient film that never drags, Secretary sweetly nurtures its story, revelling in every moment of the audience’s anticipation. It is a rare romance that leaves you never knowing what to expect next and eager to find out.

Lee Holloway wearing restraints carries a letter in her teeth

In the opening scene, we encounter Lee Holloway (Maggie Gyllenhaal) looking prim and proper in secretarial attire, but wearing a collar with a horizontal pole extending from it to her left and right. Her hands are cuffed to each end as if she’s being crucified. She floats around an opulent office awash in vibrant colours, carrying out menial office duties. She staples with one hand and makes coffee with the other. She grabs a letter from a typewriter with her teeth and disappears down the corridor. The peculiarity here isn’t the fetish gear she is restrained by; it is the peaceful look of contentment on her face.

Six months earlier, we meet Lee again, looking a lot mousier, leaving the hospital. We learn that Lee grew up in a highly dysfunctional family. Her overprotective mother and alcoholic and abusive father have caused her much pain—leading to her low self-esteem and deep depression. After an accident during a routine case of self-harm, Lee was sent to “The Institute,” where she was given the best psychiatric care available.

Lee returns home, but preferred life in the psych ward: everything was more comfortable there. Now she’s back at home, having to deal with all of life’s subtle and disturbing complications. She’s awkward, shy, and extremely fragile. She finds little comfort in her dysfunctional family life and finds it hard to assert even the mildest amount of independence. 

Lee and her mother have dinner, Lee eats a tiny morsel of food with pleasure
Lee treats herself to a morsel of potato and two peas

She attends her drearily conventional sister’s dreary, conventional wedding. These few minutes are so dull in comparison to the opening scene—and distinctly less colourful—that you’re tempted to see the introduction as a surreal dream. And because Secretary lures you into dismissing the beginning, what happens later is still surprising.

Mr. Grey would be for most people the worst boss. He’s a lawyer, yet the first questions he asks Lee in her job interview are enough to justify a mammoth sexual harassment lawsuit that would ruin the career of every living male—even if they were the world’s greatest feminist. Every query is illegal. Are you pregnant? Do you plan to get pregnant? Do you live in an apartment? He probes Lee’s personal life, and poor naïve Lee responds dutifully. When he warns her that the work is boring, she becomes more spirited, insisting that she wants to be bored. A simple secretarial position is ideal—a job that will enable her to be an adult without complicating her life. All she wants to do is follow instructions and perform mundane tasks. Herein lies the beginning of my spiritual sisterhood with Lee. It is a running joke here at 25YL that I will be the one eager to do the most tedious of tasks. It is not martyrdom; I want and need to do this. I can’t really explain the satisfaction and calmness I feel when I have to endure a mass data entry exercise.

Mr. Grey’s requirements of Lee, however, become preposterous and demeaning. Only typewriters are permitted in his grandiose offices—none of those new-fangled word processors—so Lee must retype letters in their entirety if she makes a mistake. Mr. Grey enthusiastically circles errors with red markers, thrusting the letters back in her face. He cruelly sends Lee to the trash to fetch a folder, only to tell her he has found another copy when she returns. He chucks Lee’s gift of doughnuts into the bin without any regard for how that would make her feel. He orders Lee to stop sniffling and start wearing a hairnet because he can’t stand her playing with her hair. We watch, growing more and more horrified, wondering what terrible abuse is going to come next, not yet realising that there is something else going on here.

Lee Holloway on her hands and knees with an envelope in her mouth in Secretary

But there are some clues. The previous secretary’s tearful exit as Lee arrives; Mr. Grey’s strange reaction whenever Lee follows an unreasonable order without complaint (and his erratic behaviour in general); his feeble attempts at controlling the impulse to violate Lee’s work with the red marker. There are signs, too though that Mr. Grey is no monster. He nurtures his beautiful plants with such love and care; he carefully frees the mice he catches in his Have-A-Heart traps, unharmed. His surrealistically lavish offices become an exotic sanctuary for Lee.

Lee and Mr. Grey are forging a strong psychological and sexual bond. Though she doesn’t yet understand it, Mr. Grey is giving Lee what she wants, even needs. Their deep connection first emerges when Mr. Grey helps Lee stop the self-mutilation. He forces her to discuss it, demonstrating that he understands exactly why she cuts herself in the brief monologue that pours from him. Is it that sometimes the pain inside has to come to the surface? Yes. And when you see evidence of the pain inside, you finally know you are really here? Yes. Then when you watch the wound heal, it’s comforting, isn’t it? Yes, it is. Mr. Grey tells Lee gently but firmly that she is not going to do it anymore. Walking home after their exchange, Lee realises that she feels nurtured and held by Mr. Grey. Despite his treatment of her, he’s the first person who has really cared about her and what she needs.

It is ludicrous to think that someone who has been cutting herself since she was eleven years old can just stop at someone’s say-so. Past efforts to conquer her compulsion, including her six-month spell in hospital, have all failed spectacularly. The very first day of her release from the institution, she presses a boiling teapot against her thigh, driven to compulsion by yet another skirmish between her alcoholic father and battered mother. Yet it works. It works because it is an order from him, and Lee’s desire to do what he says has become stronger than the compulsion to hurt herself. Mr. Grey must sense it, because the next day, he summons Lee into his office for her first spanking. Their dominant/submissive relationship is finally explicit—but not overtly sexual. Not yet.

Lee bends over to be spanked

You could argue that Lee has merely replaced one harmful urge for another. That might even be true…if the dominant party were someone other than Mr. Grey. He sees straight away that there’s something unusual about Lee, even remarking on it during her job interview. There’s something about you. You’re…closed. “I know,” Lee admits. Mr. Grey may have his own needs to feed, but he is attuned to Lee like nobody else in her life—not her parents, not her sister, and most certainly not her wimpy boyfriend, Peter (Jeremy Davies), whom everyone assumes is a perfect match for Lee because he is similarly mousey and shy.

Despite their S&M role-playing, we never once sense that Lee is unsafe with Mr. Grey—on the contrary. With him, she is learning to accept who she is and to express her masochism in less harmful activities. In contrast, Secretary plays out the appallingly abusive relationship between Lee’s mother and father. What Lee has with Mr. Grey isn’t anything like that.

Mr. Grey, however, does not accept himself. Like Lee, he struggles against conventional ideas of what is normal. Even though Lee makes it more than obvious that she is a keen participant in their games, a part of him is still caged by socially-imposed inhibitions. He stops playing the games for a time, but Lee provokes him ever more strongly by “misbehaving,” finally resorting to giving him an earthworm in an envelope. It’s too much for Mr. Grey—he masturbates onto her naked buttocks instead of spanking her, but he still can’t admit to his sexual and emotional need for her.

Lee Holloway bends over the desk and looks over her shoulder at Mr Grey

Mr. Grey loathes himself so much that he cannot believe that Lee really craves what he gives her. Perhaps she’s so unable to stick up for herself that she can’t say no. It is not the sign of a bad person that he didn’t want to take advantage of a vulnerable woman. Mr. Grey may be the dominant party, but he is even more insecure than Lee. Wracked with guilt, he goes so far as to fire Lee, because he says he won’t stop if he doesn’t. “I’m sorry. I don’t know why I am this way,” Mr. Grey apologises. Lee is furious—no evidence of the weakling she is supposed to be—yet Mr. Grey still doesn’t trust it. “We can’t do this 24 hours a day,” he argues. “Why not!?” Lee asks but gets no response.

Lee tries to replicate her relationship with Mr. Grey by meeting new men through the classifieds, but they’re slaves to their hilarious sexual kinks and not interested in her as a person. At the other end of the relationship spectrum, Lee has a great friendship with Peter, but no sexual chemistry. She reluctantly agrees to marry him, but in the climactic sequence of events, Lee finds the power within herself and thrusts Peter aside. She returns to Mr. Grey’s office to declare her love for him. His response is to say she only thinks she loves him, but it’s not real.

The ending is about Lee proving otherwise. Mr. Grey, still uncertain about their relationship, tests Lee by commanding her to sit in his chair without moving her hands or feet until he returns. Lee willingly complies, despite being forced to wet her dress since she is not allowed to use the toilet. He then summons Peter to his office, assuming that Lee’s fiancé will make her change her mind. Peter does not. When he manages to dislodge Lee from her position at the desk, she hits him. Lee is no meek wallflower—not anymore. During her employment at The Law Offices of E. Edward Grey, she has matured, found confidence and is in touch with her needs.

Lee submits to Mr. Grey not from a position of weakness, but a position of strength. Peter asks her why she’s doing this, and she replies, “Because I want to”. This is a declaration of empowerment. She sits at the desk because she wants to follow Mr. Grey’s orders and because she loves him. She is not being compelled to do anything. She is not handing over control of her life to someone else; she is in control for the first time.

This is the message Lee sends with her three-day vigil. Hours pass, as several family members, friends, and complete strangers sometimes, individually visit Lee to attempt to dissuade or encourage her while Grey watches from afar. He is completely taken by Lee’s compliance. Lee’s refusal to leave the office has gained news coverage from the media, which they believe to be a hunger strike. Three days later, Grey returns to the office and takes Lee to a room upstairs where he bathes and feeds her. The pair marry and happily continue their dominant-submissive relationship.

Mr Grey carries Lee Holloway home in her wedding dress

So that’s the romance taken care of, what about the comedy? Well, Secretary is funny too. In addition to the understated humour and dry wit in the performances and language, screenwriter Erin Cressidy Wilson and director Stephen Shainberg play around with extraordinary and ironic situations. One of the funniest is when Lee is hanging out by the pool with her sister and her sister’s friends, who are discussing sexual harassment at work. One of them, they feel, should sue her boss for making mild sexual insinuations. Lee enthusiastically pipes up that Mr. Grey is representing a woman in a sexual harassment case and is an excellent lawyer. “He’s the best!” Gyllenhaal delivers the line sincerely, with barely a hint of the colossal irony in her remark.

During Lee’s three days sat at Mr. Grey’s desk, a woman drops a pile of feminist literature in front of her and implores her to read about the struggle of women. Traditional feminist thinking would, of course, see Lee’s behaviour as incompatible with feminine equality. The assumption would be that Lee is objectified, used, and the living treasury of all Mr. Grey’s abusive male desires. There may even be a grain of truth in that initially, but their rapport blossoms into something much greater than a vehicle to fulfil frustrated needs. The dynamics of their relationship are distinctly individual and have nothing to do with gender.

You could make almost exactly the same movie with a male ‘Lee’ and a Ms. Grey…or with two men…or with two women. Only when the male is dominant and the female is submissive do people insist on seeing the relationship as an expression of society’s patriarchal power structure.

A tougher question is whether a healthy relationship can grow from desires born of illness. Most mental health specialists would agree that Lee and Mr. Grey’s impulses are probably a product of dysfunctional family situations and abusive childhood experiences. What if they are? If sexual turn-ons are imprinted in our psyches by our early formative experiences, there’s little any of us can do to alter them. The goal in most other cases would be not to suppress them and deny our true nature, but to channel our desires healthily. There is nothing wrong with alternative sexuality, Secretary argues, if it is consensual and no one gets hurt (at least, no one who doesn’t want to get hurt). Lee reads a book about “coming out” as a dom/sub, making the case that S&M is just another sexual preference among a multitude of human desires.

Lee bends over the desk with Mr Grey behind her, she smiles erotically

Regardless of how you feel about S&M, it’s hard to argue that Secretary is not erotic. It’s rousing to watch two people bond so intensely—their sexual wiring is electric and through it, their passion and devotion awaken. What I love most about this movie is that Secretary embraces its characters instead of condemning them or fixing them. Rather, Lee’s “issues” lead to something beautiful; two people coming together in body and soul—a miracle under any circumstances, and about as enchanting and tender a love story can get.


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Written by Laura Stewart

Laura is the Assistant Editor-In-Chief, a Writer and Hand to the Webmaster at 25YL. She has been part of the team since May 2017 when she began writing about her favourite TV show of all time: Twin Peaks. She currently Heads the Film, News and Gaming Departments.

Lula Fortune (Wild at Heart) and Lee Holloway (Secretary) are her spirit animals. Her other hobbies include singing horribly and rarely sleeping.

Laura lives down by the sea in Gower, Wales, with her husband and very special little boy.

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