‘Sleeping With Other People’ (2015), ‘When Harry Met Sally…’ (1989), and the Mortifying Ideal of Being Known

One of the persistent conventions of romance is that romantic love and friendship exist exclusively. In popular media especially, it’s almost a foregone conclusion that the desire for friendship precludes any possibility of romance and vice versa. It’s why the idea of ‘the friend-zone’ exists, why any mention of being “just friends” stings would-be lovers as sharply as outright rejection; it’s why film after film centers its story on the sweet torture of longing for a friend or the painfully cathartic journey from friends to lovers. There is something endlessly watchable about the metamorphosis of a relationship, about seeing one thing become something else completely. Of course, the choice between platonic companion and romantic interest is by no means an inherently difficult one, nor does it necessarily entail transformation; sometimes, in love romantic or otherwise, the answers are easy and clear-cut. But whether the choice is a struggle or no choice at all, whether it’s love at first sight or something a bit more complicated, it would seem that every relationship must eventually boil down to the inevitable question: are we friends or are we something more?

Harry and Sally pictured on a split screen talking on the phone in bed.
Harry and Sally commiserate over the phone while watching Casablanca. Image courtesy of Columbia Pictures.

The problem with this question is, however, the same as with all dichotomies: the choices it presents are limited at best and obstructive at worst—despite their mutual tendencies for metamorphosis, friendship does not always become romance as the caterpillar becomes the butterfly. That type of change denotes inevitable forward progress and irreversibility, and it fails to acknowledge the world of ever-shifting possibilities that exists in between. Friendship and love are not the immutable steps of a relationship’s life-cycle, but rather two ends of a spectrum: our relationships an ever-shifting point on a line that, at any given time, will veer towards one end or the other. The two experiences are intimately involved and inextricably connected and surprisingly malleable, even and especially when they seem firmly at odds: the same stories that put romance and companionship in opposition by taking their audiences through the lovely agony of the friend-to-lover arc also consistently show the sublime points of intersection, the dazzling spaces in which romance and friendship not only coexist but intertwine. Even the most rigid friend-lover divides wander into these hazy in-betweens, where being friends and being in love feel much like the same thing. It is in that space that we’ve gotten some of the most moving and tender friendships and romances the genre has to offer, including Rob Reiner’s beloved 1989 film, When Harry Met Sally… (furthermore referred to as WHMS) and Leslye Headland’s woefully under-sung 2015 film, Sleeping with Other People (furthermore referred to as SWOP).

WHMS, of course, is a blueprint for films like SWOP; as one of the great friends-to-lovers romances, it’s easy to see where Nora Ephron’s screenplay would inspire hundreds more like it. It’s a masterclass in subtlety, patience, and the delicious burn of longing. The film focuses on Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan), who, after years of casual acquaintance, make the purposeful decision to become friends, despite Harry’s protestations that it’s biologically impossible. Of course, in a way, he’s right—as they become closer, the question of sex—and by extension, romance—looms larger and larger, but they silently ignore it in order to preserve their friendship. SWOP borrows from this premise and gives it a more modern, almost grittier sensibility: Jake (Jason Sudekis) and Lainey (Alison Brie) fall out of touch after losing their virginities to each other in college, only to meet up again years later at an anonymous sex addicts’ meeting. They go on a date, but it quickly turns into a sort of confessional in which Jake and Lainey reveal to each other their unhealthy sexual behaviors. At the end of the night, they, too, make a choice: neither of them needs another opportunity to worsen their destructive habits, so they actively resist them in becoming friends instead of lovers. Unlike Harry and Sally before them, Jake and Lainey openly admit their mutual sexual attraction as a way to cope with the lures of their base impulses, but they still end up in the exact same place: with each wondering how to be in love with their best friend.

Jake and Lainey hold hands while dancing at a child's birthday party.
Jake and Lainey dance at a friend’s child’s birthday party. Image courtesy of IFC Films.

These films occupy radically different spaces in the romantic comedy canon—one being a critically-acclaimed classic and the other being a newish, well-liked but generally unknown entry—but they are natural peers for more than just their shared genre: both meditate on the idea that, despite the premiums that society places on them, sex and romantic love have their limits. Harry, Sally, Jake and Lainey all discover that it is not enough to be physically attracted to someone or to get along with them or even to love them; compatibility is something wholistic, something deeper than, “Is this person marriage material?” or “Will this person satisfy me?” Of course romance is not all dramatic kisses in the rain and running through airports—but it should certainly be more than a guaranteed date at family reunions or an escape from the wilds of the dating world. This is Sally’s reasoning for breaking up with her longtime boyfriend Joe (Steven Ford), but still, her foolish-but-wise friend Marie—played with care by the inimitable Carrie Fisher—laments her loss: “But you guys were a couple. You had someone to go places with. You had a date on national holidays!” It should be a quick, casual line, insignificant bordering on throw-away, but this is an Nora Ephron screenplay, where every syllable counts, so Marie’s funny protest cuts to the quick of the issue: sex, dating, and romance are often used an easy escape from the heavy burdens of loneliness and uncertainty, and as such, they do not consistently foster meaningful relationships. Attraction is all about putting our best foot forward, and so, by design, emotional depth is difficult to come by, for being open and honest means laying bare for lovers our less lovable, decidedly unmarketable traits. This is what makes Harry clear on the best part of his and Sally’s friendship: “The great thing is, I don’t have to lie because I’m not always thinking about how to get her into bed. I can just be myself.” With friends (read: without sex) there is no pressure to fulfill some perfect romantic ideal, no pressure to be a caricature of ourselves; everything comes easily and without judgment. If attraction is about putting only our best foot forward, then friendship is about stepping fully into the light, warts and all.

In this way, Sally’s Joe and Lainey’s Matthew Sobvechik (Adam Scott) are romantic partners in the purest, most traditional sense: they offer sexual intimacy, a sense of desirability, the prospect of stability. They are there, to go places with, to sleep with, to date on national holidays, to do a satisfactory job in fulfilling a temporary need, but these are empty offerings. Matthew’s constant presence at the fringes of Lainey’s life creates an illusion of possibility, a future in which his terminal boringness and cruel indifference will fade away to something more—“I guess… I guess, I just thought he’d eventually choose me. And so I always chose him,”—but in the end, being there is not the same as being present. Matthew and Lainey have undeniable connection, twisted though it may be, but it offers no emotional vulnerability. He doesn’t want any part of Lainey that doesn’t serve his needs. There is no sense of understanding. The same goes for Sally and Joe: she tells Harry that, at their beginning, she and Joe wanted all the same things—no traditional relationship trajectory of marriage and kids. “We’d say we were so lucky we have this wonderful relationship, we can have sex on the kitchen floor and not worry about the kids walking in. We can fly off to Rome on a moment’s notice.” It felt like the perfect relationship, and at certain points, it probably was. But as time went on, authenticity came creeping in, and the version of Sally where no marriage and no kids was enough, where the excitement of loving and feeling loved seemed like reasonable substitutes for openness and vulnerability, was no longer the version she saw in the mirror, and her illusion of possibility was shattered: “I went home, and I said, ‘The thing is, Joe, we never do fly off to Rome on a moment’s notice.’” “And the kitchen floor?” Harry asks. “Not once. It’s this very cold, hard Mexican ceramic tile.” The idea of romance is an intoxicating one, but, as WHMS and SWOP show, it does not guarantee the things we crave most in our partnerships. What, then, makes the ideal lover?

Harry runs his hand through Sally's hair on her bed as she cries about her ex-boyfriend's engagement.
Harry comforts Sally after she learns of her ex-boyfriend’s engagement. Image courtesy of Columbia Pictures.

The answer, as Harry and Sally and Jake and Lainey demonstrate, is friendship. Each couple discovers their compatibility not because of love at first sight or physical attraction—although those are certainly elements of their relationships—but because of the emotional bond forged in vulnerability. With the possibility of sex out of the way, a sort of bubble of security emerges between each couple, a safe space in which there is no need for editing or embellishing or artifice. They feel endlessly at liberty with each other, aided by the crowded anonymity of the city setting, an anonymity well-understood by both Reiner and Headland who, even in bustling restaurants and congested streets, manage to create engrossing frames where their protagonists feel like the only people left alive. Intimacy comes in big moments as well as small: Jake talks Lainey through a panic attack brought on by a text from Matthew, and Sally helps Harry put down the rug at his new bachelor pad. They talk, they wander, and they become more of themselves. The ease and comfort between them is palpable and contagious, so that watching each film feels like opening the door into an impenetrable friendship and being welcomed with open arms.

Harry and Sally talk while walking through Central Park in the fall.
Harry and Sally alone and anonymous in Central Park, getting to know each other. Image courtesy of Columbia Pictures.

And then, suddenly, there is a shift. Harry and Sally and Jake and Lainey look up to find themselves in that place on the spectrum of friendship and romance where the two become almost indistinguishable, and suddenly the question of sex—and romantic love—is once again front and center. Harry comforts Sally after she learns of her ex-boyfriend’s newly-minted engagement, and as she rambles on about her un-loveable traits and the ravages of time, you can see the depth of the love in Harry’s eyes, a depth made possible only in friendship. When they finally fall into bed together, it feels natural; they already know each other so well, of course they would want to know each other in that way. Jake comforts Lainey after a particularly cruel encounter with Matthew, and as he sweetly, sensuously, and affectionately puts his friend to bed, she asks, “Are we in love with each other?” It’s a lovely, deeply poignant moment that surpasses even Ephron’s screenplay and that best captures the pathos of both films: Jake give a silent confirmation, and when Lainey asks what they should do about their love, he answers with a sad smile: “Nothing. There’s nothing to do. I love you for free, Lainey.”

Lainey kisses Jake's hand in front of a moving truck.
“Thank you for teaching me how to love.” Image courtesy of IFC Films.

So we arrive back at our original question: are they friends or are they something more? But it is no longer a question of “or”; both couples are both friends and something more, and for that, their love is all the better. They each love the other for free, warts and all. Harry tells Sally, “I love that you get cold when it’s 71 degrees out. I love that it takes an hour and a half to order a sandwich. I love that you get a little crinkle above your nose when you’re looking at me like I’m nuts… And it’s not because I’m lonely, and it’s not because it’s New Year’s Eve. I came here tonight because when you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible.” What WHMS and SWOP teach us is that this is love at its best: complex and uncompromising. These are stories about learning to be friends, learning how to love, and learning that, in the end, it’s really the same thing.