Re-Watching My Best Friend's Wedding 20 Years Later — I Have Some Questions

7. Jules’ gay friend George should have been the lead. (Image credit; YouTube/MovieClips)

7. Jules’ gay friend George should have been the lead. (Image credit; YouTube/MovieClips)

When My Best Friend’s Wedding debuted in theaters, I was in middle school. I went to see it with my mom and older sister, and I loooooved it. The setting was Chicago — I was enamored with cities. The genre was rom-com — my lifelong devotion to their cause was just beginning to bud. The lead was Julia Roberts — no one can resist peak Roberts.

So on Monday night, at home and too tired to read, I was delighted to see My Best Friend’s Wedding playing on cable, and settled in to relive the good times.

But the times were not good, friends. The times, I realized (1997, to be precise), had not been good at all.

It’s extraordinary the way 20 years can impact one’s response to a movie. Of course, I’ve changed (one hopes, at least...). More importantly, the culture has also traversed a ways since the late 90s.

Watching My Best Friend’s Wedding now feels akin to culture shock. But I was alive then! So insists my brain. But… was I? Have I somehow wiped certain aspects of my beloved 90s from the ol’ memory?

Because, I gotta tell you, I do not remember all this mess:

1. Leading man Michael is blah and blech. 

Image Credit: YouTube/Movieclips

The plot of My Best Friend’s Wedding is pretty well summed up in the title. Jules (Julia Roberts) and Michael (an unforgivably unlikeable Dylan McDermott) were besties in college and throughout their early 20s. They’ve had a pact that if both were single when they turned 28 (28!), they would get married. Jules remembers said backup plan upon the cusp of their birthdays, right before Michael calls to announce he’s engaged to preternaturally chirpy Kimmy (Cameron Diaz), and won’t Jules please come to the wedding (happening basically the next day)? Jules thinks she’s in love with Michael and sets about trying to break the “happy” couple up.

Where do I begin with the problems with this? Michael’s a solid starting place:

A. He’s handsome, but not jaw-droppingly so. Which means he must be charming, except…

B. He is not charming at all. He is beige; vanilla. Which means he must be warm and kind, except…

C. He is one of the most selfish male leads I’ve ever encountered. His confidence and self-obsession rival that of Jacob (Ryan Gosling) from Crazy Stupid Love, except Michael has none of Jacob's gruff Bond suave and sensitive soul lurking just behind the douche suit. Which means he must offer some other winning quality, except…

D. Michael has zero winning qualities.

How am I supposed to believe two women played by Cameron Diaz and Julia flippin’ Roberts would flop all over their gorgeous selves for this dude?

2. “Love” apparently means letting someone hug you in public.

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When Jules asks Michael what makes Kimmy so special, he says she lets him “hold her as long as I want,” even in public.

Shakespeare this is not.

3. Michael is begging Jules to end this wedding, but then marries Kimmy anyway.


Question One: How would the average woman feel if her fiancé entered the dressing room of his ex, stayed even after noting said ex was in just her lingerie and scrambling to cover up, then slyly commented on how he’d seen her “more naked” than that — all before sauntering out with this relationship-killing admission: “You look good… without your clothes on.”

Question Two: How would the average woman feel if her fiancé admitted to his ex that he felt “crazy jealous” when he found out she was engaged?

Question Three: How would the average woman feel if her fiancé spent the afternoon before his wedding with his ex, on a boat, slow dancing to the tune of his own voice singing “their” song — “Just Thinking Of You,” aka Sinatra’s top tribute to true-blue love?

Question Four: How would the average woman feel if her fiancé removed her wedding ring from his ex’s finger by sucking it off with his mouth?

I could go on. Michael is desperate for Jules to give him a reason to leave Kimmy, but Jules is too chicken to admit her feelings (until it is apparently too late), and so Michael ties the knot with a woman he obviously doesn’t have the deep feels for.

My guess is if Kimmy were a coherent and even marginally honest person, and she learned of all these enduring feelings between Michael and Jules getting explored just 48 hours before the wedding, she’d react like any other coherent and marginally honest person:

Run for the hills. 

4. The wardrobe department should have asked for better funding.  

Image Credit: YouTube/Quickflix

I’ve personally known middle school assistant principals with better fitting suits than what “rumpled old” Michael wears.

And Julia Roberts is the only person on planet Earth who could pull off Jules’ outfits. Multiple blazers appear in various shades of beige and brown, all roughly five sizes too big, draped over baggy pants.

Was this the look of “serious” people in their late twenties? Why, 90s? Why?

5. Sober grown woman sits on lap of ex's father at a rando baseball game, then they share a brief a lip-on-lip kiss. (???)


I’m not here to judge. I have just never plopped down on the lap of any older fella, let alone my ex’s father, not to mention in a public setting.

Papa Joe, I don’t hold it against you. We’re talking about Julia Roberts here.

But… I mean. Did this happen? Like, out there in '90s reality?

6. Kimmy is not old enough to be at the karaoke bar.

Image Credit: YouTube/Nikola

It’s a key scene in the film, and Kimmy orders alcohol, but we all know Kimmy is only 20. And this seems pretty lazy from a directorial standpoint, to skip over the little I.D. hurdle and pretend no one gets carded.

I’m 34 and I get carded, and I don’t even have Cameron Diaz’s porcelain skin. So I want to see Kimmy get carded. I want to see Michael explain she’s his underage fiancé. I want to see the bouncer and other bar flies give him a much deserved stink eye.

I get none of this.

7. Jules’ gay friend George should have been the lead.



If I asked anyone who has ever seen this movie if they are more excited to see Michael or George walk into a scene, the answer would be George. Always, always George.

He’s hilarious, he’s smooth, he’s honest. Besides Diaz, he’s the only one who can hold his own in a scene with Roberts (a pretty impossible feat, to be fair).

But look, the rationale is right there in the title. We can focus on the "wedding" or we can focus on the "best friend," aka George: the new and epically improved replacement for Michael. 

8. A straight-up dysfunctional relationship “wins.”



If it’s not clear yet, Michael and Kimmy aren’t on the same level.

In a brutally painful (and PUBLIC) fight, Michael responds to Kimmy’s request that he take a stable job with her father over his endless travel with this:

“What am I supposed to do with my job, huh?... You’re damn straight that’s how I feel. Just come out and say it. My job’s not good enough. I’m not good enough… I’m supposed to just roll over and drool? Alright. I’m the asshole. I’m the insensitive sexist asshole, and you’d be better off without me.”

Gee, when you put it like that, Michael...

He says all of this in a tone best described as “snarling.” By the end, Kimmy is in tears, whimpering, and he still looks damn near ready to throw something at her.

Kimmy’s response to this beratement is to scream, “NO, NO!” and literally beg Michael to stay with her, because otherwise she’ll “just die.”


In fact, WHAT?! was my reaction to pretty much this entire film. 

I don't know what I was thinking in middle school, but let's add my evolution on this film to the long list of reasons I'm glad I don't have to live there anymore.

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