Twenty years ago, Valentine’s Day at the movies would have been very different. A sexually explicit drama about young lovers who engage in BDSM play would have mustered a niche release, probably straight-to-DVD or late night on HBO following an episode of Real Sex. Meanwhile, an innocuous rom-com starring Hugh Grant would have opened on over 3,000 screens and been #1 at the box office. Obviously, a lot has changed. Fifty Shades of Gray was an enormous success last weekend, bringing in over $80 million domestically, while The Rewrite, starring Grant and Marisa Tomei, screened at only one Manhattan theater and was otherwise available only on VOD.

It would be tempting to extrapolate from this a thesis on the changing state of American sexuality, but the truth is that The Rewrite is just not very good, and its low-key release is more likely the result of its poor overall quality. The script is filled with clichés, relying so heavily on the conventions of the ‘90s rom-com that it borders on a Seltzer-Friedberg parody of the genre, while its lack of a visual style would be considered inadequate even by the standards of a network sitcom.

But The Rewrite does succeed at one thing: It makes the best argument for killing the traditional rom-com once and for all. It’s not just that the movie is bad. Rather, it demonstrates how impossible it is to square the progressive gender politics required of films today with the regressive tendencies of the rom-com.

These days, films that rely on antiquated, regressive social values are a major non-starter with pop culture critics. The popularity of the Bechdel Test, which measures a film’s commitment to gender equality, has brought these values into the mainstream, and Hollywood has responded by producing a wide variety of stories with strong, female protagonists over the last few years. Many of these seek to reverse specific tropes that have dominated film for much of its history; Maleficent, Snow White and the Huntsman, and Into the Woods recast fairy tales with a feminist slant, while the success of The Hunger Games and the Divergent series provide strong, complex female heroes for America’s youth.

To its credit, writer/director Marc Lawrence tries to reflect these realities in The Rewrite, but the restrictions of his genre make it impossible. His protagonist, Keith Michaels, is an Oscar-winning screenwriter who can’t get a new project greenlit because the brainless studio executives all want something with “a kickass girl.” Lawrence makes it clear that this type of feminism is not rooted in any real quest for equality; the execs are just shameless capitalists trying to cash in on the latest trend. So the audience is supposed to sympathize with Keith, who refuses to give them a female-centric story and instead seems more capable only of making a male film like, well, The Rewrite.

Out of options in Hollywood, Keith eventually takes a job teaching at an upstate New York university, where he quickly emerges as a full-blown misogynist. Tasked with picking his students based on screenplay samples they submitted, he ditches the scripts and simply creates a roster of attractive young coeds, with a few nerdy guys thrown in for cover. His first night in town, he sleeps with one of his students, but his misogyny doesn’t go public until later that night at a staff cocktail hour, where he runs aground of an esteemed Jane Austen professor (Allison Janney), whom he tells that he is “a little tired of female empowerment.”

The film does not explicitly endorse Keith’s misogyny. We’re not supposed to approve of his behavior, although, since he is our protagonist, we inevitably empathize with him and root for him to succeed, as we often do with the loveless middle-aged men in need of redemption that have populated rom-coms since the 1930s.

And at first glance, The Rewrite is an improvement on those, at least when it comes to gender relations. In an old-fashioned rom-com, our protagonist would find redemption in a much younger woman who teaches him how to enjoy life again. In The Rewrite, Keith falls for Molly (Marisa Tomei), a single mom of two daughters finishing her degree in her forties (A sign of Keith’s gender bias: When Molly tells him that she loves to watch his movie with her “girls,” he wishfully assumes at first she is a lesbian).

But while it could read as progressive for the protagonist of a rom-com to fall for some someone closer to his own age (in real life, Tomei is only 4 years younger than Grant), Molly is really just a slightly more wrinkled version of the notorious Manic Pixie Dream Girl. She lives by a carefree, live-for-the-moment ethos that is usually attributed to younger people in our society. While there is some logic behind this character attribute – a person reinventing herself in her forties might very well embrace such a lifestyle – it reduces her to a one-note character that exists only to serve Keith’s journey to redemption.

More troubling is the film’s shocking sex-negativity in its depiction of Karen (Bella Heathecoate), Keith’s first lover. Karen is the only female character who is interested in sex at all (Keith never actually sleeps with Molly in the film). She aggressively hits on him the first night she meets him, and they engage in a short-lived but presumably energetic love affair. Pairing an aging male celebrity with a young coed is problematic from the start, but the more disturbing stuff is still to come. When he breaks up with her, she becomes vengeful, threatening, and even unstable. Keith ultimately diagnoses her attraction to him as a sublimated desire for affection and acceptance from her remote father. In other words, The Rewrite can only understand female sexuality as some sort of misplaced psychological dysfunction.

But at least dysfunction implies some sort of inner life. Karen is still one of the most complex female characters in the film. As noted above, Molly is just a bubbly vehicle for Keith to improve his life. Meanwhile, Keith’s female students are a roster of clichés seemingly designed to fill quotas. There is the death-obsessed Asian goth girl; the perky but dumb Jewish brunette; the bubbly redhead; and the um, black girl, who has no evident personality at all.

Of course, some of these mistakes are purely artistic failures, not social ones. It is certainly possible to draw even minor characters with specificity, and a more generous, less spiteful portrayal of Karen would certainly have produced a more sex-positive message. And yet it is hard to imagine a romantic comedy with a male, hetero protagonist being read as anything but misogynistic in our era of hyper-sensitivity to social progress in pop culture. Such a film inevitably revolves around a male character finding self-actualization through a woman, a notion that our current wave of feminists have roundly – and rightly – rejected.

Still, I believe there is hope for the rom-com. Last year’s What If and 2012’s Celeste and Jesse Forever employ dual, male-female protagonists and approach love and sex from a more equitable perspective. And it is easy to imagine a real modernization of the genre arriving through an exploration of same-sex relationships or transgender protagonists. Until then, the artistic and financial failures of The Rewrite should drive a stake through the heart of the ‘90s-era rom-com once and for all, and I doubt anyone will complain.