What does it take for a romantic comedy to be both conventional and surprising at the same time? It takes a smart application of familiar ingredients, a couple risks (not all of which pay off), and a surplus of appealing actors. In this way, How to Be Single is an instruction manual on assembling something that feels sort of progressive while also delivering exactly what we’re expecting.
A film that name checks Sex and the City at least once, How to Be Single operates as kind of a millennial version of that show, though only Rebel Wilson, the erstwhile “Fat Amy” from the Pitch Perfect movies, fits neatly into her package as the Samantha. Though I suppose Dakota Johnson (herself an “erstwhile,” of Fifty Shades of Grey fame) maps out to being the Carrie, Alison Brie the Charlotte, and Leslie Mann the Miranda. These women are indeed navigating single life in the city that never sleeps, their approaches to finding a man (or many men) differing from one another based on experience and general life philosophy. Johnson, like Carrie, is the main character, the one who provides occasional narration and seems to make the most disastrous decisions on the road to self-discovery. Brie, like Charlotte, is the organized one with a systematic plan, which of course is also destined to fail her. Mann, like Miranda, seems to be the oldest and most mature (just don’t check Wikipedia, which will tell you that Cynthia Nixon is actually the youngest of the four Sex and the City actresses). And Wilson just wants to party and wake up next to as many unknown penises as she cannot quite remember. On the way to finding the right man – or not – each has her worldview challenged in some way before emerging with a truer understanding of herself.
It’s the not finding the right man part we might want to focus on here. Most romantic comedies are schematic enough that it’s easy to telegraph who will end up with whom, because a meet cute followed by playful dislike always ensues, and during the “rough” initial period of flirtatious fighting, that soul mate usually demonstrates some perfect way he or she gets the essential personality of the other. Obstacles will be thrown between them, but we know those people are destined to be together, simply because that’s satisfying, and a romantic comedy is nothing if not eager to please. How to Be Single, on the other hand, is unafraid to fake us out on a couple apparently destined couplings, even to leave some of its characters possibly still searching by the time the end credits roll.
Of course, for every risk a movie like this takes, it has to double down on something familiar just to hedge its bets. And so indeed we get Wilson playing the brassy, overly confident comic relief once again, we get Johnson and Mann tugging at our heart strings with moments of exquisite sentimentality, and we get Brie bringing massive quantities of charm. Each actress has done something like this before, and yet each kind of feels like they’re collaborating on something new. And yet a second time, everything we expect in the modern version of one of these stories is also present: the female friendship that must be privileged over any romantic relationship, the character who decides to have a baby without a man (right before meeting just the right man), and the character who makes spreadsheets on what she wants from a partner, only to meet a contender who doesn’t tick any of her boxes. To remind us of how musty this all is, the soundtrack is replete with on-the-nose selections, and nearly every holiday on the calendar is celebrated, with the notable exception of Valentine’s Day (even though this film was released in the U.S. just before the 14th of February).
And yet yet again, there’s a freshness and likeability factor about this film that actual grows as the narrative unfolds. It must be traceable to the cast. Johnson and Mann are the standouts, though they’ve got some supporting players worth mentioning as well. Damon Wayans Jr. is particularly touching as a suitor who’s grieving the death of his wife while raising his daughter as a single dad, and Jake Lacy brings a buoyancy that gives him great chemistry with Mann, more than a decade his senior. Many of the relationship norms of a movie like this are thus challenged. A cynic might consider this just a PC answer to the overly safe pairings in most rom coms, but How to Be Single is the type of movie that tends to squash cynicism. It might even awaken your inner romantic.