It’s often said that fashion and the popular culture influenced by it exist on a 20-year scale, whereby the clothes we wore and media we consumed two decades ago suddenly begin to come back in style. It happened in the 2000s with the ‘80s and again in the 2010s with the ‘90s. But if we’re given to believe that now, inexplicably over a year into the 2020s, that the fashion and pop culture of 2001 are back, two words spring to mind: brace yourselves. Because while certain cultural texts do stand the test of time and are never finished saying what they have to say, others persevere only out of sheer youthful nostalgia and we tend to ignore their blaringly problematic elements. The Wedding Planner is part of the latter.

It’s not news: The Wedding Planner was made as merely a cozy romantic comedy with an expected happy ending. And like all romcoms of its era (and any era, really), its purposely simple formula contributes to the enduring appeal of the genre at large: yes, most are similar and predictable, but they often feature loveable and compelling characters in situations some viewers relate to or, at best, aspire to relate to. This is why it’s often difficult to judge what’s being fed to us, especially when we’re young, because all we see is the formulaic characters in the formulaic setting headed towards their formulaic ending. And for the most part, that’s fine. But once you grow up and rewatch a picture perfect romcom with fresh eyes, its flaws are often hard to ignore.

The Wedding Planner was surely designed to be an endearingly loveable movie. Jennifer Lopez, in the midst of a blooming career in pop music, became the first and still the only person to achieve a number one film and a number one album in the same week: a star whose versatility as a performer is still underrated. Matthew McConaughey, well, speaks for himself: he was gorgeous then and he’s gorgeous now. Judy Greer makes her first of several supporting romcom roles as the best friend and a pre-“Grey’s Anatomy” Justin Chambers co-stars as a childhood friend of Lopez’s character, featuring quite possibly the worst Italian accent ever committed to film. It’s doubtful if The Wedding Planner would still feature so prominently under grown-up sections of streaming platforms if the studio had gotten either of their first two choices of lead actors: Jennifer Love Hewitt and Brendan Fraser, or Sarah Michelle Gellar and Freddie Prinze, Jr.

So why is it a terrible movie, you ask? Well, first and foremost, we must consider the fact that dreamy Dr. Steve or “Eddie” (McConaughey) completely leads on Mary (Lopez) into believing he was available to her, despite the fact that Mary is already knee-deep in planning their wedding with his fiancée Fran (Bridgette Wilson-Sampras). It’s a silly romantic comedy after all, and at the time holding men accountable to their garbage actions was supposedly not as trendy as it is now, so we can just roll our eyes and excuse that, right? But then it gets worse.

As Mary—a stereotypical, anal-retentive young wedding planner to whom everyone reacts in shock at the fact that she’s still single—continues to plan the wedding for the man she so obviously has feelings for (even persuading them to chose the world’s worst wedding song, Olivia Newton-John’s “I Honestly Love You”), her Italian father (Alex Rocco) keeps trying to set her up with Massimo (Chambers), the infamous “boy who ate mud.” Massimo offers Mary a heartfelt proposal, one that makes her father and family act like she would be a fool to turn down and one that prompts her father to confess that he and Mary’s mother had an arranged marriage that caused her mother great pain. And yet, here he is, now trying to throw his own daughter into that same toxic culture, a gesture that implies the viewer is supposed to sympathize with him because his heart was in the right place. It’s hard to tell which is worse: a father trying to spin a cautionary tale about arranged marriage into an excuse for his daughter to marry the first guy who offers, or the fact that we’re supposed to buy that Jennifer Lopez is Italian.

It’s no secret that The Wedding Planner makes clear that a woman’s life only begins when she gets married or finds love. No matter how far feminism progresses, it’s hard to watch any romantic comedy from the last 30 years and not find that that’s still the only takeaway. The implication here is that Mary can’t possibly be happy working as a single wedding planner in an industry that profits from and thrives on heterosexual dominion. She’s gifted at making weddings look as perfect and magical as possible, so the logical conclusion is that she must have a rich and happy personal life: only to cut to a scene of Mary arriving home to an immaculately organized apartment, making dinner and watching “Antiques Roadshow.” The film wants us to believe that every woman deserves (read: needs) a happy ending with another person, especially a woman who has dedicated her life to creating magical weddings for other couples. Even if it’s to a man who completely led her on while being engaged to someone else, or to a simple-minded immigrant whom she hasn’t seen since childhood. The moral of the story is: Mary Fiore deserved better choices.

The Wedding Planner is far from the first romantic comedy to reinforce toxic, heteronormative gender roles and ceremonies, and it will be far from the last. Seven years later in 2008, 20th Century Fox released a similar story starring Katherine Heigl called 27 Dresses in which a similar professionally dedicated 30-something devotes all of her free time to being a bridesmaid. But that film ends up being more of a cautionary tale about the perils of people-pleasing and featured more male characters you could actually root for. (As opposed to Steve Edison, who deserves nothing.) As romcoms from the early ‘00s like The Wedding Planner begin to enter their golden age of nostalgic rebranding, it’s still important to remember that very few cultural texts hold up perfectly through time and that some do worse than others. In other words, if you’re looking for a J.Lo romantic comedy to rewatch, pick Maid in Manhattan.

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