Dark tower demolished.
I shouldn’t be surprised that my nineteen-year old self wasn’t a fan of The Wedding Planner when it came out. Romantic comedies weren’t my genre of choice and I surely didn’t pick it upon going to the theater with friends. So I probably watched with an immovable bias, honed in on its familiarity, and ignored its strength with an agenda to walk out without laughing. Watching it almost twenty years later removed from that teenage boy mentality, however, reveals how strong preconceptions can prove. That’s not to say Adam Shankman‘s film is a masterpiece—far from it. But it’s also not a failure to deliver on its promise of romance or comedy. While the latter is definitely more successful, there’s enough charm for the former to satisfy too.
Screenwriters Pamela Falk and Michael Ellis get the ball rolling with the opposite of love: cutthroat business. Their lead Mary Fiore (Jennifer Lopez) built a career on planning weddings, but any magic that celebration used to bring as a little girl is gone. Does she care whether or not the bride and groom belong together? Nope. She’s been doing this long enough to understand the odds of divorce and has hardened herself to no longer caring beyond her ability to turn every event into a smoothly operated machine minus hiccups. If that means drugging family members to keep them from ruining things or manipulating someone out of his/her cold feet with a carefully manufactured lie, so be it. Mary’s an artist who paints with lovers rather than love.
That in and of itself puts a nicely cynical spin on the proceedings. This isn’t the first film to thaw its jaded protagonist into reclaiming the hope for happiness that’s been rendered fantasy. Nor is it the first to mock itself on that journey with an abundance of absurdity via a cartoonish supporting cast motivated by silliness above narrative purpose. Despite its structural conventions, though, it still works to keep us engaged and entertained. A big key to this can be attributed to a shocking level of authenticity where complexity of its central love triangle is concerned. Because when most rom/coms like this would tirelessly show the lead as our champion, this one can’t stop from making her the pettily jealous third wheel devoid of humility.
As such, the comparisons to My Best Friend’s Wedding are unavoidable. Like with that 1997 Julia Roberts starrer’s “other woman” beyond reproach, this one seeks to supply the same. The result isn’t as effective since Fran Donolly (Bridgette Wilson-Sampras) comes with the baggage of being a Type-A personality from a rich family unafraid to coerce her fiancée into getting her way. But she is still likeable as far as being someone in love. There’s no road with which to let Mary earn our sympathy if she decides to sabotage Fran’s wedding (which she’s ironically planning). That she would coincidentally run into the groom (Matthew McConaughey‘s Steve Edison) and unknowingly go on a “date” with him to spark mutual feelings doesn’t give her sufficient cause to ruin Fran’s life.
What The Wedding Planner does get unequivocally right is its authentic depiction of how this difficult (but hardly impossible) situation would unfold. Because Mary and Steve’s interaction didn’t end in a kiss (although his putting himself in the position where one was possible shouldn’t be understated), there’s nothing to stop the business relationship connecting them. The ensuing awkwardness therefore allows the audience to enjoy some nice barbs on behalf of both characters while Fran smiles in the background, completely oblivious to the underlying intent. The animosity is interestingly less about Mary and Steve’s connection, though, than the desire to rub their respective hypocrisy in their faces (a misunderstanding involving Alex Rocco as her father arranging a match with Justin Chambers‘ Massimo makes it appear she too is engaged).
But that banter never risks treachery. She’s not trying to steal him from Fran and he’s not trying to dump Fran because he loves Mary. They’re actually learning about themselves and understanding their desires as individuals instead. So rather than jump from one relationship to the next, they’re using the fact that they almost did to step back and figure out what’s wrong. Why has Mary become so indifferent to love? Why has Steve drifted from a relationship that’s become more about routine than want? It’s specifically because they would never act on their impulses by making it about removing Fran (a good person at heart) from the picture that lets us respect them and hope for their happiness regardless of whether it’s predicated upon them being together.
The fact that it’s a Hollywood studio film of course means that it must be, though. (But how great would the ending have been if the happily ever after for both was specifically one away from each other?) So despite some really poignant moments of looking inwards at the end, the pieces do ultimately fall exactly where you know they will the moment Steve saves Mary from a runaway dumpster. Thankfully the journey to that overwrought inevitability gives us enough to laugh at and think about so as not to overshadow the emotional work being done. That we can find Fran and Massimo endearing to the point of wanting their happiness above the leads is a victory in my mind. Wilson-Sampras and Chambers quite often steal the show.
Because it’s about Mary and Steve, however, we must take a leap of faith as far as excusing a lot of their actions. Between his “being a guy who saw an opportunity” and her using Massimo’s love as something she can benefit from, it’s not easy to remain in their corners. We do because the film demands it and because they do the right thing every once in a while to make up for past transgressions. They’re ultimately the least interesting characters of the whole (a supporting cast rounded out by Judy Greer, Joanna Gleason, Fred Willard, and Lou Myers ensures it), but that’s okay. The others needing to have epiphanies to clear Mary and Steve’s path towards each other is convenient, but the reverse would have been worse.