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When Romance Met Comedy

With When Romance Met Comedy, Caroline Siede examines the history of the rom-com through the years, one happily ever after (or not) at a time.

I thought long and hard about what movie I should pick to cap off this column’s four-year journey into the rom-com genre. Should I make a nostalgic play for a ’90s favorite like Never Been Kissed? Delve into Hollywood history to explore an influential classic like It Happened One Night? Finally figure out how the hell to talk about Woody Allen? In the end, I decided to go with something that best represents the type of movie I’ve been most interested in exploring in this column: a good-not-great studio comedy that puts women front and center—one with a little more emotional and artistic depth than its naysayers might acknowledge. A movie like 2016’s How To Be Single.

The stars and writer of How To Be Single would argue that it isn’t a romantic comedy at all. They preferred to think of it as a female-led comedy for Valentine’s Day. How To Be Single was released at a curious turning point —a few years after the contemporary concept of feminism had become mainstream, but two years away from the rom-com revival that kicked off with Crazy Rich Asians and Netflix’s “Summer of Love” slate. After the heyday of the 1990s renaissance gave way to the glut of the 2000s, rom-coms had to go underground for a while. By 2016, the genre didn’t exactly know what it was anymore, which is a fitting time to release a movie all about finding yourself.

Though the poster sells How To Be Single as a Sex And The City-style story about four female friends making their way in New York together, the actual structure is less formulaic than that. It’s a companion piece of sorts to 2009’s He’s Just Not That Into You, one of the big ensemble rom-coms that sprung up in the wake of Love Actually’s Christmas domination. A lot of the same creative team are involved, including producer Drew Barrymore, who was set to direct at one point. But where He’s Just Not That Into You felt cloying and a little desperate, How To Be Single is sweet, funny, and surprisingly wistful. It feels like a movie that was made by a cast and crew who actually cared about what they were doing, which is perhaps the biggest factor separating a mediocre rom-com from a good one.

At the center of it all is Alice (Dakota Johnson), a self-proclaimed relationship girl who spent all four years of college dating her boyfriend, Josh (Succession’s Nicholas Braun). Determined to spend at least some time on her own before settling down, Alice requests a “break” as she and Josh both head to New York City. (“Uh, there’s no such thing as a ‘break,’ season-three Ross,” one character retorts after hearing that rather naïve plan.) Once in the city for her “sexual Rumspringa,” Alice encounters all sorts of living examples of what single life can look like: Her proudly irresponsible party-girl co-worker, Robin (Rebel Wilson); her career focused OB/GYN older sister, Meg (Leslie Mann); a hot playboy bartender named Tom (Anders Holm) who becomes her on-call hook-up; and Lucy (Alison Brie), the Type-A, marriage-obsessed serial online dater who catches Tom’s eye even though she’s a far cry from his usual type.

There are other characters in How To Be Single’s tapestry of New York. Jake Lacy’s Ken is the affable, much younger guy who falls for Meg just as she gets pregnant via IVF. And Damon Wayans Jr.’s David is a successful single dad who meets cute with Alice at an alumni event. Though some critics dinged the movie for lacking a strong central through line, I actually think that’s a feature, not a bug. Particularly in your 20s, there’s a certain fluidity to your life, as friendships fall by the wayside when you find yourself in a new relationship or a casual hook-up toes the line between friendship and something more. How To Be Single plays around with structure and tone in order to capture that experience. Sometimes, Tom feels like one of the potential romantic interests vying for Alice’s heart, and other times he’s more like the lead in his own rom-com subplot with Lucy—one that offers a pointed subversion of a nearly identical thread in He’s Just Not That Into You.

Of course, How To Be Single has many of the rom-com genre’s pitfalls, too. It’s aggressively heterosexual and egregiously white, especially for 2016. It’s also the rare romantic comedy that I wish were longer, as just about every character could’ve benefited from about 10 more minutes of screentime (especially Wayans Jr.). Yet I also appreciate that its unusual structure means you can never quite put your finger on where it’s going. Between director Christian Ditter (Love, Rosie), initial writers Abby Kohn and Marc Silverstein (Never Been Kissed, He’s Just Not That Into You, I Feel Pretty), and later writer Dana Fox (The Wedding Date, What Happens In Vegas), How To Be Single is the work of creators deeply steeped in rom-com tropes. And they have a keen sense for when to lean into them and when to playfully subvert them.

Ditter also brings a welcome visual flair, favoring location shooting and amber-hued natural lighting over the kind of flat, front-lit faces you often see in studio comedies. As in a movie like (500) Days Of Summer, a little style goes a long way towards jazzing up a genre that can sometimes look same-y. There’s a gorgeous crane shot near the end of the film where Alice retreats to a fire escape several stories up and the camera frames her like she’s floating in the sky.

Working on set with Fox and a cast of game improvisers, Ditter also encouraged a wonderful naturalism from his actors. The characters do that great rom-com thing of actually laughing at each other’s jokes. And Johnson and Mann particularly excel in the chemistry department, giving Alice and Meg the kind of loving sisterhood that’s fueled rom-coms like Sense And Sensibility, 10 Things I Hate About You, and Your Sister’s Sister. How To Be Single can get away with heightened punchlines because it’s taken the time to ground its characters in quieter, more casual moments first. There’s a two-minute scene of Mann just talking to a baby that’s one of the most charming things I’ve ever seen.

On the other end of the spectrum is the over-the-top yet underdeveloped Robin, who’s funny but also a scene or two away from totally working as a real character. Still, How To Be Single at least paved the way for Wilson’s future collaboration with Fox in the meta rom-com parody Isn’t It Romantic—one of my favorite romantic comedies of the past few years and a movie I strongly considered covering for this final column. Isn’t It Romantic pokes fun at romantic comedy tropes while celebrating why we love them, with career-best work from Wilson to boot. How To Be Single isn’t genre-breaking in the same way, but it has a similarly refreshing off-kilter energy, never more so than in its willingness to actually leave a handful of its characters single by the end.

Like the best romantic comedies, How To Be Single does more than just romanticize romance. It romanticizes normal life. If this movie’s version of singledom is just as glossy and idealized as any rom-com love story, well, that’s kind of the point. What makes the genre special is the way it combines the kind of heightened fantasy you might find in a superhero flick or musical with storylines that intersect with our most common lived experiences. It’s a delicate balancing act that the genre’s detractors miss when they simply dismiss it as “unrealistic.” Romantic comedies are kind of like metaphor-heavy science fiction movies: The worlds they create don’t necessarily reflect reality, but the emotions and themes they evoke do.

“Why do we always tell our stories through relationships?” Alice ponders in her opening voiceover, and How To Be Single takes that question seriously, rather than as a means to a rom-com end—an approach that dovetails with what The A.V. Club’s Katie Rife dubs “the friend-com,” female-led comedies that try to account for the “de-centering of romance in 21st-century lives.” There’s a nice balance in How To Be Single’s ultimate messaging: Take the time to really get to know yourself, but don’t be afraid to change your mind either. Meg starts as someone who thinks she’d prefer to be alone, only to get swept off her feet by an unexpected connection. Lucy wants a partner and gets one, even if he’s nothing like she’d imagined. And Alice goes from wanting to experience single life in a surface-level way to genuinely grappling with what it means to be a truly independent person.

It’s a choice that’s both quietly revolutionary and part of a grand rom-com tradition. 1953’s Roman Holiday, 1987’s Broadcast News, and 1997’s My Best Friend’s Wedding also end with their heroines on unexpected paths to happiness. In fact, in many ways, How To Be Single isn’t so much breaking the mold as just highlighting what rom-coms have long done best. The gender role reversal in Meg and Ken’s sweet dynamic echoes 1945’s Christmas In Connecticut, while Alice and Robin’s “best friends above all” bond rings out just as loud and clear in 1953’s Gentlemen Prefer Blondes.

If there’s one thing I’ve learned from writing about over 100 romantic comedies from five different countries across 83 years of filmmaking history, it’s that few actually fall neatly into the stereotypical boxes that we think characterize the genre. Sure, there are trope-filled movies like How To Lose A Guy In 10 Days and The Wedding Planner, along with terrible rom-coms like The Ugly Truth, Something Borrowed, and Failure To Launch. And, of course, there are some romantic comedies, like When Harry Met Sally and The Wedding Singer, that deliver a straight-down-the-middle love story so perfect it’s impossible to fault them for it. But more often than not, the romantic comedy genre has much more to offer than just romance.

There are rom-coms about friendship (The Best Man, Four Weddings And A Funeral), rom-coms about family (Saving Face, My Big Fat Greek Wedding), rom-coms about careers (His Girl Friday, Love & Basketball), and rom-coms about morality (The Apartment, Dirty Dancing). And once you immerse yourself in the genre, you can see how much these movies are all in conversation with each other, echoing and elevating stories that date all the way back to Shakespeare and Jane Austen.

I began this column with Bridget Jones’s Diary because I wanted to make the case that, above all, romantic comedies have long been our greatest haven for women’s stories. They’re the place where generations of Hollywood actresses have most consistently been able to show off their comedy chops, from Katharine Hepburn posing as a gangster in Bringing Up Baby to Regina Hall stealing the show in About Last Night to Rebel Wilson climbing through a car window in How To Be Single. And they’re one of the few genres where complicated female protagonists reliably get to experience the kind of big screen self-actualization journeys that are usually reserved for men.

From the outside, romantic comedies can look like cheap fairy-tale wish fulfillment hawked at an undiscerning audience. From the inside, however, they’re a place where Tracy Lord, Holly Golightly, Monica Wright, Claudine Price, Cher Horowitz, Andie Walsh, Marisa Ventura, Stella Payne, Lucy Moderatz, Jane Nichols, Lara Jean Covey, Loretta Castorini, Elle Woods, and Alice Kepley can claim the cinematic space to find themselves. The real love story of the rom-com genre is between its audience and the three-dimensional female protagonists it’s created over the years. And the true comfort behind these comfort watches is the idea that, just like these films’ complicated leading ladies (whether partnered or single), you’re going to be okay, just as you are.

Goodbye for now: Thank you so much for following along on this four-year journey into the romantic comedy genre. It’s been a joy to read your insightful (and funny!) comments, and I’m incredibly grateful to The A.V. Club editors who’ve given this column such a supportive home over the years. If you’d like to keep up with me, you can find me over on Twitter or on my podcast Role Calling (where I’m currently chatting about Meg Ryan’s career!). And if you need a rom-com to watch tonight, my top five favorites are The Wedding Singer, When Harry Met Sally, Love & Basketball, Notting Hill, and The Philadelphia Story, with honorable mentions to Saving Face, Boomerang, Long Shot, Moonstruck, and Breakfast At Tiffany’s.

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