The Wedding Planner exists in an alternate universe. It’s a universe where Jennifer Lopez not only plays an Italian woman, Mary Fiore, but one where she also wears pastels and hot pink lip gloss—all anomalies. Mary nerds out over her Scrabble matches (it’s how her parents learned English after moving here from…Italy), but she’s also hip to the latest trends for her job as a wedding planner. Everything about Adam Shankman’s debut feature feels just a little off; it’s strangely wrong in an ethereal way, fit only for the rom-com genre. As The Wedding Planner celebrates its 20th anniversary, it’s time to catch up with two rom-com legends (J.Lo and Matthew McConaughey, of course) and unpack some of the film’s unearthliness.
The rom-com is about Mary, a wedding planner who helplessly falls for one of her clients, Steve (McConaughey). Whereas there might be some leeway in other work relationships, romance with a client is usually prohibited in the wedding business—because, obviously, they’re engaged. Adding to the many surreal elements of The Wedding Planner is Mary and Steve’s meet-cute, which feels like it could be stripped straight from a superhero movie’s introductory action sequence. A helpless civilian, stranded in the middle of the street. Impending danger headed her way. A handsome stranger bound to catch her breath and save her life in one charming swoop. The Wedding Planner’s meet-cute is one of the finest specimens of the trope, primarily because the bizarre sequence feels like something straight from a fever dream. Because what’s a meet-cute, if not incredibly surreal?
Mary and Steve’s romantic fate all comes down to one pesky ice cream cone. Mary, always the workaholic, breezes across town with her phone attached to her ear, chatting up her coworker Penny (Judy Greer). She dons a pastel purple dress with a beige overcoat—again, something J. Lo would never wear—and, notably, brand new Gucci heels. Caught in a world of wedding planning, as always, Mary’s too busy to notice a huge dilemma headed her way. As she dashes across a hilly San Francisco street, her little heel slips into a grate. No, not her new Gucci shoes! In agony, she crouches to fetch the shoe from the grate, but it’s too stuck to retrieve.
Planted in the middle of the street, trying to yank her shoe free, Mary has naively put herself in grave danger. While I’m no San Francisco expert, this looks like a major road. There are no cars headed her way, yet there’s bound to be one soon. But even if there were a car coming, a driver could stop, honk or yell out the window before ramming into J.Lo, ever the shoeaholic. So The Wedding Planner raises the stakes: Instead of a car (which has brakes) headed her way, it must be a large, unstoppable inanimate object. Like a dumpster.
We have to rewind to the ice cream mentioned earlier to discover the origins of this rolling, rambling heap of garbage. While J.Lo tugs at her shoe, the film cuts to a nearby taxi driver enjoying a vanilla cone. Only, his car is in motion—don’t eat and drive!—and this sweet treat is distracting him from the road. Spilling a glob of cream into the seat next to him, the guy swerves and brushes his cab into a roadside dumpster, freeing it and sending it flying towards our helpless wedding planner. Do not forget: This movie is set in San Francisco, where there are many hills. So many hills, in fact, that random objects are (apparently) constantly in deadly motion. One blink and you could miss a dumpster headed straight to knock you out.
Now, just like I’m no San Francisco expert, I’m no dumpster expert. But I’m contemplating how a small sedan taxicab could release a wheeled dumpster lodged on a curbside, full of heavy garbage and probably rusted enough to be stuck in one place. Wouldn’t the wheels be locked? The car brushes the side of the garbage mound, sending it in the opposite direction towards Mary. The taxi doesn’t even hit the thing at full force—the car just sideswipes it. This doesn’t add up.
Nevertheless, here comes the dumpster, and Mary is still trying to rip her new Gucci shoe from the street. She needs to stop tugging on it and gracefully maneuver it through the hole; alas, under pressure, Mary is not as thoughtful as the weddings she so carefully executes. Nearby, a gorgeously sun-soaked man exits his parked vehicle (hope he didn’t forget the parking brake—this is San Francisco!) and notices Mary’s dilemma. Though there are plenty of other folks around to assist Mary with her shoe, the handsome man dashes up in the nick of time, sweeping Mary out of the dumpster’s path right before it clocks her. And look! She even saved her Gucci shoe.
The good-looking man who saved Mary was Steve, naturally, marking their chaotic first interaction of many. The hubbub ends with Steve on top of Mary, an important touch of physicality to introduce their chemistry. They get up, Mary says he smells of sweet plums and grilled cheese, then promptly faints in his arms. Then, there is Steve’s pediatric hospital, more flirting and Judy Greer, who busts into the situation shouting, “What I don’t understand is how she got near the dumpster. And what happened with the shoe?” just like the rest of us. Thank you, Judy Greer, for always being the voice of reason.
There’s plenty of drama after this incredible meet-cute sequence—like a scene where Steve accidentally castrates a statue and, in the process of tacking it back on, Mary glues her hand to the figure’s nether regions—but for now, it’s best to bask in the glory of a fantastically wild meet-cute. J.Lo’s stellar performance in The Wedding Planner went on to garner a few awards nominations: She nabbed the Kid’s Choice Award for Best Actress, and was even nominated for the Razzies’ Worst Actress category for this film and Angel Eyes. That unforgettable meet-cute is undoubtedly to thank for these accolades. If The Wedding Planner has taught us anything in the past two decades, it’s to beware the hills of San Francisco, never eat and drive, and avoid grates while sporting Gucci heels. May all of our dreams and our love lives be as berserk as this wonderful scene.
Fletcher Peters is a New York-based journalist whose writing has appeared in Decider, Jezebel, and Film School Rejects, among other spots. You can follow her on Twitter @fIetcherpeters gossiping about rom-coms, TV, and the latest celebrity drama.