Sleeping With Other People, and the Asshole's Quest for True Love

“Men and women can’t be friends, because the sex part always gets in the way,” Harry famously tells Sally at the beginning of Nora Ephron’s classic 1989 romantic comedy When Harry Met Sally. “Men and women can’t be friends,” parrots Natasha Lyonne, best friend to the Sally of Leslye Headland’s new movie Sleeping With Other People. It’s natural that with time, the line’s gotten shorter and more to the point; Headland’s versions of Harry and Sally (Jake and Lainey, played by Jason Sudeikis and Alison Brie) are much more upfront about the limits of their friendship than their predecessors, though that doesn’t stop them from going through the whole complicated rigamarole anyway.

The premise of Sleeping With Other People appears less complicated than it ends up being. Jake and Lainey lost their virginities to each other in college in a one-night stand. Over a decade later, Lainey is still involved in a complicated fuck-buddy relationship with a guy who won’t commit to her (played by an almost unrecognizably cold Adam Scott), and Jake finds himself cheating on every woman he gets involved with so he can avoid breaking up with them. As is typically the case in this oeuvre, we are dealing with the issues of privileged New York City dwellers, where the careers and lives of those involved in the film’s central relationship play the role of tertiary characters.

Lainey and Jake bump into each other again at a sex addiction meeting, and while the pair each have issues that they lovingly stroke like pets they’re claiming they really want to give up—the way many of us do with our neuroses—the issue of whether or not they are really sex addicts is quickly forgotten. Instead, it’s replaced by their burgeoning codependent relationship, set up at the beginning with the acknowledgment that they’re attracted to each other but will not act on it.

Phone calls late at night, walks through Central Park, and explicit conversations about orgasms ensue, none of which appear to be accidental homages; Headland admitted at Sundance that the film was “basically When Harry Met Sally for assholes.” Headland’s strength, as it was in her play-turned-film Bachelorette, is theatrically funny one-liners and complex, uncomfortable relationships between her characters. But despite the subject matter here being just as full of potential as her last film Bachelorette, that movie was darker, with more edge. Though Bachelorette also had comedy mainstays Will Ferrell and Adam McKay producing, Headland’s lost some of her bite with this second feature. Sleeping With Other People loses speed at the end, twisting and turning around plot changes that start to feel wholly unbelievable, no matter how invested we’ve become in Lainey and Jake, or Jake’s very funny best friend and his wife (played by Jason Mantzoukas and Andrea Savage), or even his prickly boss (played by Amanda Peet), who he persistently tries to woo even while emotionally attached to Lainey.

“Want to talk about it?” Lainey asks Jake at one point. “Talk about what?” he counters. “We’re not a couple but we act like it,” she says matter-of-factly. On the one hand, its refreshing how the two don’t dance around their relationship, but the degree to which they acknowledge their attraction without acting on it also stretches the limits of believability with regards to human self-control.

It’s timely that just this week, Rob Reiner, the director of When Harry Met Sally, called modern romantic comedies “soft-core porn,” listing Sleeping With Other People and Trainwreck as movies that are more sexually explicit than he’d apparently like. The film certainly warrants its R-rating for its sexual content, but despite Reiner’s protest, that’s not really the hardest part to swallow. What’s the crassest is Headland’s devotion to her characters getting what they want despite their often terrible choices and poor treatment of others (she did call them assholes, after all). It takes until the end of the film to realize that although they’re very witty, you might not actually think Lainey and Jake are particularly good people. (In a rare turn of events, Headland’s made a movie where a female character’s motives and drives are better explored and fleshed out than those of the male lead.)

That’s a direction romantic comedies of yore were perhaps less willing to explore. For all her anxiety, Sally wasn’t more self-destructive than she was sweet and earnest. For all his neuroticism, Harry was more absent-minded than he was hurtful. Lainey and Jake might just be self-involved people who think they’re funnier than they are, but they found each other, and they get to get their happy ending too, even if we don’t always want to hear about it.