For a movie that features a professional pickup artist as its romantic leading man, Hitch has a surprisingly insightful central thesis: It’s sleazy, misogynistic dudes who make contemporary dating difficult for both women and men. The existence of these creeps forces women to be guarded and to couch their true emotions in social niceties in order to protect themselves. That sucks for women, but it also sucks for genuinely well-meaning men who also have to participate in the confusing social dance of modern dating—all because terrible men have ruined everyone’s ability to be honest and vulnerable.

With When Romance Met Comedy, Caroline Siede examines the history of the rom-com through the years, one happily ever after (or not) at a time.

It’s an intriguing idea around which to build a movie about modern courtship. It’s not, however, something this goofy 2005 Will Smith vehicle is even remotely capable of handling with the nuance it requires. For one thing, the idea that men can be easily divided into “good guys” and “sleazy guys” is a myth that ignores the complicated ways in which ingrained sexism actually operates, while giving men who view themselves as “good guys” an excuse for not analyzing their own behavior. For another, it’s hard to invest too much in the philosophical musings of a movie that thinks the height of comedy is Kevin James forgetting to put his pants on before walking out of a bathroom.

Hitch is Will Smith’s first and so far only foray into the romantic comedy genre (give or take a Jersey Girl cameo). So in addition to positioning him as its romantic lead, the film also finds a way to get Smith into the familiar buddy comedy dynamic that had become his signature thanks to movies like Bad Boys, Independence Day,  Men In Black, and Wild Wild West. Smith plays Alex “Hitch” Hitchens, a professional dating consultation (a.k.a. “date doctor”) who helps awkward men win over the objects of their affection. His most hapless client is Albert Brennaman (James), a schlubby tax consultant who’s pining after one of his firm’s clients, the gorgeous celebrity heiress Allegra Cole (Amber Valletta). But as Hitch improves Albert’s dating game, he suddenly finds himself unable to maintain his own level of suaveness as he tries to woo no-nonsense gossip columnist Sara Melas (Eva Mendes). Sara, meanwhile, decides to write an exposé about the mysterious “date doctor” she’s heard rumors about—not realizing he’s actually the man she’s currently dating.

Hitch was released in the midst of the early 2000s rom-com boom, as Hollywood started trying to capitalize on the genre’s 1990s creative renaissance in increasingly formulaic ways. It remains the sole credit of screenwriter Kevin Bisch, and was directed by rom-com vet Andy Tennant, who had previously helmed Fools Rush In, Ever After, and Sweet Home Alabama. Although it received mixed reviews, Hitch was a huge financial success. Domestically, it remains the third-highest-grossing rom-com of all time (behind My Big Fat Greek Wedding and What Women Want). And it grossed a worldwide total of over $368 million on a $70 million budget. A big part of that is no doubt thanks to Smith’s superstardom. And while in many ways Hitch feels like an average, slapstick-reliant early 2000s rom-com, Smith’s casting immediately sets it apart in one major way.

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The romantic comedy genre is notorious for its lack of diversity, and while there have been some great rom-coms with black leads, they tend to be unfairly treated as a subgenre aimed mostly at black audiences. Given Will Smith’s mega-stardom, Hitch was very much designed to break that trend and appeal to a broader audience. Thus a lot of thought went into who should play Smith’s leading lady. According to Smith (who also produced Hitch), the filmmakers discussed whether casting a black female lead would hurt the film internationally and whether casting a white female lead would be too controversial for American audiences. In the end, they went with Cuban-American Eva Mendes for the role.

There’s certainly a much larger conversation to be had about Hollywood’s trend (particularly in the early 2000s) of casting Latina women against black men and potentially freezing out black women from roles in the process. But within the rom-com genre in particular, it’s refreshing to see a romance centered on an interracial couple in which both members are people of color, which is still relatively rare on screen. Mendes is one of the best parts of the movie, and when Hitch works, it’s thanks largely to the easy chemistry she and Smith have together. But the film is also very much aiming for a “color blind” ethos. Hitch never overtly references race, even as it can’t seem to stop discussing its central battle-of-the-sexes gender dynamic.

Hitch has a tricky tightrope to walk with its protagonist. Hitch’s arc is about learning that love isn’t an equation you can solve because there aren’t actually any rules to romantic attraction—it turns out Allegra likes Albert because of his flaws, not because of any of the “coolness” Hitch coaxed out of him. But Hitch doesn’t want its protagonist to be too much of an asshole either. Thus it takes great pains to establish him as the most ethical pickup artist in the world. (The film never actually uses the “pickup artist” moniker itself, just “date doctor” or “consultant.”) Hitch works exclusively with good-hearted men who are looking for long-term relationships, and he actively disdains playboys who are just looking to trick women into sleeping with them. Yet more often than not, Hitch’s methods are successful and his nerdy clients do wind up in bed with the far more conventionally attractive women they’re pursuing. That’s one of the many things that leaves Hitch feeling so muddled. The film ends with Hitch humbly admitting that there are no rules to dating, but the beginning of the film shows that Hitch’s rules do indeed work. So which is it?

To its credit, Hitch has its protagonist offer some genuinely good advice to the men he’s coaching: Listen to women; treat them as human beings, not objects to be worshipped or ogled; and make sure they always feel physically comfortable and able to consent. (Hitch advises Albert that when a man initiates a first kiss he should move in 90 percent of the way and then let the woman come the other 10.) Yet Hitch definitely still positions women as prizes to be won, leaving little room for the idea that women might have their own foibles, hang-ups, or preferences when it comes to dating. In his opening monologue, Hitch announces, “No matter what, no matter when, no matter who—any man has a chance to sweep any woman off her feet.” That’s after he informs men that when women kindly reject their advances, they’re lying to them or at the very least just confused about what they actually want.

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Again, the fact that Hitch eventually has Hitch refute his own philosophy is what makes the film’s thesis so hard to parse. (There’s also a whole through-line about Hitch hawking romance while himself being a guarded cynic who’s traumatized by a failed college relationship.) But it’s certainly not hard to see someone coming away from the film with the message that “no” doesn’t actually mean “no” in a romantic context, which is a deeply troubling social norm with some terrible real-world implications.

Even for those who don’t take that message from the film, Hitch serves as a reminder that women are seldom given the same wish fulfillment narratives as men—even in a genre explicitly marketed to them. When Hitch offers the female equivalent of someone desperately in need of a “date doctor” in Sara’s friend Casey (Julie Ann Emery), she’s likable, thin, and conventionally attractive. As the rom-com genre perpetually reminds us, lovelorn female protagonists don’t get to look like Kevin James. They look like Drew Barrymore or Ginnifer Goodwin or Katherine Heigl or Renée Zellweger with a couple extra pounds.

Yet in a weird way, Hitch winds up underserving its men as much as its women. The movie is so caught up in capturing the moments in which Allegra starts to fall for Albert, that it never actually stops to explain why he’s so in love with her in the first place, other than the fact that she’s stunning. Hitch shames women for what it believes to be their overly judgmental natures (Hitch claims his job is to get women out of their own way so great guys like Albert have a fighting chance), yet it simultaneously takes it as a given that all men want to be with the hottest women possible, regardless of whether they actually have anything in common.

Hitch isn’t entirely lacking in insights about the female experience. There’s a good scene where we watch Sara’s frustrations slowly build as a bar patron refuses to take her “no” as a “no.” And the film’s ultimate message about our flaws and vulnerabilities being what makes us lovable is fine fodder for a breezy rom-com. But in a genre that at its best regularly allows women to be protagonists in their own stories, it’s frustrating to watch Hitch return to the more common cultural script about men being subjects and women being objects in romantic narratives.

In other words, Hitch is a mess, and not just because of its overly complicated plot mechanics, underdeveloped subplots, and vanishing supporting characters. It’s not unwatchable. Smith delivers his signature charisma and Mendes brings a huge amount of humanity to a character who could otherwise have been just a type-A stereotype. The film uses Kevin James well without overusing him. And Hitch ends with a final dance montage so charming that it almost makes you forget about all the problematic stuff that came before it. Yet the fact that Hitch falls back on lazy gender stereotypes while leaving just enough wiggle room for viewers to misinterpret its message probably means the bad outweighs the good on this one. Parks And Recreation once imagined a future where Jaden Smith stars in Hitch 2: Son Of A Hitch. If Hollywood ever gets around to making that one, hopefully it will have better gender politics.

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Next time: The beautiful melancholy of Breakfast At Tiffany’s.