Watching My Best Friend’s Wedding With Rom-Com Director (and Superfan) Leslye Headland

My Best Friend's Wedding. Photo: Maya Robinson and Photo by TriStar Pictures/Courtesy Everett Collection

This post originally ran in April 2015. We are rerunning it with the theatrical release of Sleeping With Other People this weekend.

Leslye Headland grabs the remote and rewinds. "Wait, something is really interesting here," she says, "because I think they may have used the F-word. It’s huge!" We're watching the beloved yet divisive 1997 rom-com classic My Best Friend’s Wedding, and Headland is right: Julia Roberts (as lovelorn protagonist Julianne) dropped the expletive while explaining why her friend George (Rupert Everett) — now posing as her fiancé — has swooped down to accompany her to the big wedding. “He just came in for a few hours," said Julianne, "to, uh, fuck me.” We scream. What we have here is not just an F-bomb, but the kind that implies actual sex

It's all a little bit scandalous — not that Headland should be blushing, since her films aren't afraid of F-bombs in the least. In her directorial debut Bachelorette, Kirsten Dunst, Lizzy Caplan, and Isla Fisher played some very-R-rated bridesmaids; Headland's new film, Sleeping With Other People, which premieres at the Tribeca Film Festival tonight and opens in theaters on August 21, follows "love addicts" Jake (Jason Sudeikis) and Lainey (Alison Brie), and features a centerpiece sequence where Jake teaches Lainey how to masturbate by fingering an empty green-tea bottle. Rom-com fans will recognize that moment as a modern homage to When Harry Met Sally’s famous orgasm scene, something Headland is well aware of: “It’s not whether or not you create new tropes," she says, "but how you reinvent or execute them.”

And the film we’ve chosen to watch together subverts the single most important rom-com trope there is: Our two protagonists don’t end up together in the end. Not to mention, Roberts plays Julianne as a Marlboro Reds–smoking, F-bomb-dropping, vest-wearing ice queen. “My big thing about this movie is that today it would never make it past development. First of all, she’s smoking," says Headland, who is also smoking. "And she’s kind of a hater. [Marriage] is just not something she feels like is a priority.” My Best Friend's Wedding also takes great pains not to vilify Kimmy (Cameron Diaz), who's planning to marry Julianne's best friend Michael (Dermot Mulroney). “This movie isn’t scared that your allegiance will go back and forth," says Headland. "It’s not afraid to let you make a decision about whether or not you like someone, and then what ends up happening is that it becomes not about female friendship or sacrifice, but about identity. Does it really define you that you’re not with this person?”

My Best Friend's Wedding does fall into a number of rom-com traps. Michael isn't exactly the most compelling male lead, for one — “He is like a walking dildo, which I love," says Headland — and Kimmy warms to total stranger Julianne with such speed, you could get whiplash. “Look, do I think that it’s extremely believable that Cameron Diaz would throw her in a car and then ask her to be maid of honor?” Headland says. “No. But it does make the movie better.” Headland faced the same criticism with Bachelorette, when asked why bride-to-be Rebel Wilson would invite all these "awful women" to her wedding in the first place: "It’s a movie. That’s the conceit."

In another time, Headland sighs, during a more golden era for rom-coms, we were more accepting of such tropes. “We stopped having actual love triangles," she says. "Because the notion that a woman could move secretly between two love interests made her seem ..." Headland pauses on this one, the word unlikable on the tip of her tongue. “Okay, not unlikable, but just complicated,” she finally says, rattling off the basic loglines of rom-com classics: “Meg Ryan’s gonna marry a guy she’s not sure about, falls in love with another guy over the radio, secret; Julia Roberts is concerned her best friend is marrying someone else and she might love him, secret; Sandra Bullock tells the entire family of a man in a coma that she’s his fiancée and then falls in love with his brother, secret.”

So what happened to our rom-com golden era? When did we go from Meg Ryan faking orgasms in When Harry Met Sally to Cameron Diaz with semen in her hair in There's Something About Mary? “We’re in a weird place where the comedy overtook the romance of the rom-com," says Headland. "And so you get people like the Farrelly brothers and Judd Apatow — who are all geniuses, but they’re run by comic thread.”

We bring our attention back to My Best Friend's Wedding, waiting intently for the movie's pivotal scene: the one where the wedding party breaks out in song. “I really feel like you need to have a musical sequence in every rom-com, a dance or a sing-along,” Headland says — and she took her own advice. In Sleeping With Other People, Lainey and Jake go to a child's birthday party while high on ecstasy, and she ends up dancing to David Bowie’s “Modern Love” with a troupe of similarly sugar-addled preteens. “You need a spectacle! The musical number is something we don’t really see anymore in an earnest way.” As Rupert Everett soars through “Say a Little Prayer” on the screen in front of us, Headland notes, "Everyone is singing except for Julianne and Michael. Besides being fun and silly, [this scene] actually deepens the bond between them.”

After the song-and-dance, there's only one big scene left to anticipate: “Choose me, marry me, let me make you happy," Julianne begs Michael as we cringe, knowing it won't work out for her. I ask Headland if she could imagine writing a rom-com where the two leads don’t end up together forever. “Oh, absolutely,” she replies. Deep down, we both respond to My Best Friend's Wedding as an ode to platonic love, and when the movie ends with Michael heading off to his honeymoon, Julianne finally gets to hang with the man who's arguably her actual soul mate: George. You know, the one who happily plays fake boyfriend, gives her crucial advice, and shows up exactly when she needs him. Headland sighs, watching Julianne and George reunite for one last dance. “This moment right here," she says, as the two friends hold each other. "This is truly the most romantic moment.”