The Audacity of Dermot Mulroney

You thought you didn’t need another ’90s romcom take, but oh, you do.

I mean, who gave him permission?

I was a tomboyish teenager who grew up wearing cargo pants and sneakers, listening to Nirvana, and priding myself on my love of edgy indie films like Eraserhead and El Topo. So imagine my surprise when, in my late teens, I happened across a mainstream romantic comedy starring Julia Roberts that changed my life forever. My Best Friend’s Wedding opened an unlikely door to what would become my sincere (and somewhat secret) appreciation for romcoms, especially when watched in the fall. When I mentioned to our romcom-loving managing editor, Aly Sarafa, that this might become the subject of October’s essay for our Substack newsletter, even she—who knows so much about what makes me tick—was shocked to learn this about me. (Not the feminist poet and cultural critic into cheesy dialogue and swooning storylines!)

In the film, Julia Roberts plays Julianne, long-ago-fling-turned-lifelong-best-friend to Michael (Dermot Mulroney). For two decades, Julianne and Michael have been there for each other through thick and thin. They even have their own song—“The Way You Look Tonight” by Tony Bennett—a not-so-subtle nod to the complexities of their friendship. That’s the kind of song you might find yourself drunkenly singing with your guy bestie at a karaoke bar, only to turn and look him in the eyes and suddenly think, Oh God, we should be together, shouldn’t we? 

Aly and me screaming like hormonal teenagers in the Google Doc while editing this essay.

So goes the story of Julianne and Michael. But when Michael suddenly tells Julianne that he’s fallen in love with a woman named Kimmy (Cameron Diaz) and plans to marry her in just a few days, Julianne is forced to confront her feelings for Michael and figure out a way to stop the wedding. We watch as Julianne spends the entirety of the movie trying, in hilarious and horrifying ways, to break up Kimmy and Michael, all of which backfire spectacularly. By the end of the film, Julianne has learned a lot of hard lessons about life and being honest, and that the old adage is actually kind of true: sometimes if you love something, you really do have to let it go.

In my opinion, almost any actress can rock a leading role in a romcom—hell, I’ve even sort of been in one!—because the storylines are, in some ways at least, true to our lived experiences or mirror our unconscious fantasies, whether they speak to our romanticism, our unmanifested desires, or fulfill our emotional needs. But it takes a certain kind of man to play a believable love interest, someone who any woman would swoon for and not just because of his looks. In our romcom leading men, we need cheesy lines of dialogue delivered believably, physical affection like something out of a Danielle Steel novel, and definitely some kind of mysterious depth that makes us feel like only we can crack his code. They also need to be captivating and charismatic enough to get the audience to let their guard down and root for them, despite some very questionable decisions they may make to move the plot forward. 

The character of Michael O’Neal, perfectly played by Dermot Mulroney in My Best Friend’s Wedding, checks all these boxes and more, thereby becoming the greatest leading man in romcom history. This is where I would normally say “Don’t @ me,” but honestly, @ me all you want because I will win this argument. Unlike many of the actors who have starred in some of the most iconic romcoms over the last several decades (Bill Pullman, Hugh Grant, Billy Crystal) there’s something about Dermot’s brooding onscreen presence and offscreen persona that hypnotizes you, catching you off guard, like the football quarterback with a heart of gold you never knew you always wanted.

Allow me to enter into evidence the following receipts: Mulroney is very handsome, yes, but not in the typical pretty boy way you might assume a leading man would be; it’s this surprising ruggedness that makes him feel like an accidental romantic hero. There’s the scar that cuts into his pouting lips, the hint of a southern accent in his baritone voice, the bangs that fall perfectly across his weathered brow like he’s some worn-in cowboy hot off a day’s work teaching wild horses how to obey. There’s his dark brown eyes conveying a wealth of emotional intelligence, his swagger that cannot be defined, only felt, and his smile—like Elvis Presley with a secret, and you, dear reader, are that secret. In real life, Dermot Mulroney even has the audacity to be an accomplished cellist, possibly the most romantic musical instrument there is. (Insert me thinking about being played like a cello by Dermot Mulroney here.) What’s next? His own line of genuine leather and flannel picnic blankets that smell like his neck? Honestly.

In My Best Friend’s Wedding, there’s a scene where Michael (Mulroney), in his deep voice and slight southern drawl, tells Julianne why he loves his fiancée, Kimmy, so much: “When I hug her, even in public, I don’t have to let go right away. She lets me hold her as long as I want.” Pullman, Grant, even McConaughey could never. It is only the Depths of Dermot™—that moody, old-souled, Irish Catholic aura—that could say a line like that and get away with it.

Later in the film, the Depths of Dermot™ are proven once again in what is honestly one of the sexiest scenes in the history of film and TV, and that’s including the infamous “kneel” scene with Hot Priest from Fleabag. (I can hear my husband sarcastically saying, “Thank you for your honesty, Amber.” YOU’RE WELCOME, DAVID.) Despite a last-minute change of heart and attempt to undo her latest effort to sabotage the wedding, one of Julianne's schemes actually works, prompting Michael to (momentarily) call off the wedding. After breaking up with Kimmy over the phone from his hotel room, Michael opens his door to find that Julianne had been sitting against it waiting for him. As the door swings inward, she instantly falls back into his room, landing flat on the floor. He gets down next to her, telling her the wedding is off. Then, he asks for the ring that he’d planned to give Kimmy. Julianne, his best woman, reluctantly holds up her left hand to him with tears in her eyes, the band around her bruised ring finger, and whispers with embarrassment, “I tried it on and it won’t come off.”

Without a word, Michael leans in closer and lifts her hand up, putting her whole finger in his mouth, removing the ring slowly, revealing it clenched in his teeth as he stares deeply into her eyes. This could have been the stuff of a Fifty Shades of Grey nightmare, but instead, thanks to the Depths of Dermot™, it is one of the most touching, honest, and heart-wrenching moments in romcom history. The prosecution rests its case, Your Honor.

O, to be Julia Roberts’ finger.

Around this time every year, I watch My Best Friend’s Wedding and some of my other favorite romcoms, from the straightforward to the unexpected, the classic to the most recent: While You Were Sleeping, When Harry Met Sally, The Apartment, Sleepless in Seattle, The Big Sick. In fact, some of my favorite romcoms are not just about romantic relationships, but the romance that can also be found in friendship, like Harold and Maude or Withnail & I (two of my all-time favorite films). These kinds of movies feel like the perfect antidote to the fall equinox, when, as Dr. Mindy Nettifee beautifully explains, the natural world begins to go to seed, mirroring our own internal shifts. As the world begins to cool off, romcoms extend a kind of warmth, a sense of still-heating-up in a cooling world, if only for a heart-palpitating, butterflies-in-the-stomach-filled hour and forty-five minutes. Even naysayers like my husband, David, can’t resist the draw of a damn good romcom; he will often walk in while I’m watching one of these movies, poke fun at it, then leave. But he somehow always finds an excuse to come back into the room and watch just a little bit more.

The romantic comedy genre can transcend the corny dialogue and hard-to-believe plots because it connects us to a common, universal desire: to feel needed, loved, and awakened during a time when the natural world tells us to go inward, to quiet our cravings, and hibernate. Romantic comedies say the things we never could or never would. They are the manifestations of the risks we were afraid to take for the ones that eventually got away. They give us hope, nostalgia, and sometimes even a path toward some kind of personal closure.

In the middle of My Best Friend’s Wedding, Julianne and Michael take a scenic boat tour down the Chicago River to have a now-or-never conversation about their obvious but unsaid feelings for each other. It’s a critical moment—Michael is about to get married to Kimmy, but he still has complicated feelings for Julianne. “Kimmy says if you love someone, you say it. You say it right then, out loud. Otherwise, the moment just . . .” Michael says to Julianne. Her signature curly red hair blows in the wind as the boat floats under a bridge, shadowing them in darkness, “. . . passes you by,” Julianne whispers, finishing his sentence.

“Passes you by,” he echoes. “Yeah.”

They stare at each other in silence, as we all wonder alongside them if this is the moment they will finally tell each other the truth. But that silence goes on for far too long, and before you know it, their boat comes back out into the blinding sun of reality, and the moment is lost. The scene ends when Michael takes Julianne in his arms and softly sings their song—that song—as they begin to dance, slowly and quietly, on the deck of the boat among the crowd of tourists, knowing some things might be better left unsaid, never fully finished.

What are some of your favorite romantic comedies and why? Come cuddle up with me in the comments and tell me everything.

Speaking of romcoms, I celebrated my eleventh wedding anniversary this month with my husband, David, by forcing him to join me as the first guest on Further Ado, our new interview series. If you missed it, never fear! It’s available for All Subscribers to watch now.

And here’s a few reminders and announcements of some of the fun things we have coming up: 

• Good Riddance: Join us in the Chat for a weekly space to let go of something that’s been bugging you. Every Saturday, I’ll share something I’m letting go of and invite you to do the same. It can be big or small, serious or silly—an interaction that left you feeling not so great, a piece of clothing you’ve been hanging on to for too long, or your anger over a tragically canceled TV show that ended on a cliffhanger. For All Subscribers.

• Further Ado: Every month or so, I’ll interview an exciting guest for our video interview series on topics that aim to exhilarate, inspire, and entertain. We’ll cover everything from how to cross new creative thresholds, how to remain politically activated within the boundaries of self-care, behind-the-scenes stories from film and TV sets, and so much more. For Paid Subscribers.

• Readings + Prompts: A couple times a month, I'll share a new video made just for you reading something I've written over the years—a poem, an essay, an unpublished work (GULP)—as well as a unique prompt based on that work. Come get entertained and creatively energized. For Paid Subscribers. 

• Here, Take This, I Love You: Every month we will give away memorabilia and artifacts from the vaults of my office. A signed Joan of Arcadia script! Limited edition broadsides of poetry! Some gum Alexis Bledel once chewed! (I would never.) For Paid Subscribers.