Throwback Thursday: Way Before Fifty Shades, Maggie Gyllenhaal Was Our Perfect Secretary

Let’s throw it back to a modern kinky classic!

Hey Fleshbot fans! I consider it my mission in life to tell people about way better kinky smut than the Fifty Shades movies or books so that brings us to the topic of this week’s Throwback Thursday pick, the 2002 film Secretary starring Maggie Gyllenhaal and James Spader. I will say that Secretary comes with a content warning for the depiction of self-harm. Please take care of yourself and choose another movie if you need to.

At the beginning of the film, we meet a young woman called Lee Holloway who has just been released from an inpatient mental health program for self-harm issues and is now seeking employment. Her family is a bit of a trainwreck (aren’t they all?) and they are still treating her like a fragile child even though she is a young adult looking to move forward with her life. Her mother is still locking up the knives. And to top it off her sister is getting married. And then there’s the sorta-loser-but-sorta-sweet dude named Peter who likes her a lot more than she likes him. Life on the outside is all she remembers and less.

Lee enrolls in secretarial school where she does very well and then begins looking for jobs. She happens upon the law office of E. Edward Grey (Spader) and during their interview, he tells her that it is a very dull job and his office only uses typewriters. Lee’s up for the challenge and things move along until one day their boss-and-employee relationship veers into the sadomasochistic. We see big changes in Lee as she gets more confident in her abilities at work, stops dressing like an Amish person, and takes such submissive delight in letting Grey give her orders, but also playing brat games in her own way. Also, one of Grey’s first orders is that she will never, ever, self-harm again.

As we mentioned, Peter is still hanging on to hope, and Grey is a basket case, so he dumps Lee, afraid that their relationship has gotten too close. A heartbroken Lee agrees to marry Peter just to not be lonely. Shortly before the wedding, she tries on her gown, and something clicks in her brain and she needs to prove her devotion to Grey. I won’t spoil the end of the movie, but it’s worth the watch. Is it a perfect depiction of a perfect dynamic between two perfectly sane humans? All nope. Secretary is fundamentally a love story about two kinda fucked-up people finding their complementary human. The lid finds the pot.

Secretary is loosely based on a short story by Mary Gaitskill. Interestingly enough, Gaitskill wrote a sequel to the story telling us what happened to Debby (Lee’s name in the original story) since the end of the original story. It’s an interesting read.

Secretary is available to stream (at press time) on free streaming channel Tubi.