Sleeping With Other People: A Rom-Com By Any Other Name

Editor’s Note: Sleeping With Other People opened in limited theatrical release September 11, 2015.

When all is said and done, a rom-com by any other name (or description) is still a rom-com. Sleeping With Other People, Leslye Headland’s second film – after the raunch-filled, women-centered comedy, Bachelorette – plays the genre subversion game sophisticated moviegoers tend to enjoy until the inevitable third-act climax embraces the same genre tropes and conventions previously upended, twisted, and tweaked along the R-rated, profane way. It’s all the more disappointing because Headland’s ear for truth-revealing dialogue, while heavily stylized and anti-naturalistic, and the charming, winning performances she elicits from Alison Brie and Jason Sudeikis as a non-romantic duo trying out the “Let’s be friends” premise explored by When Harry Met Sally several decades ago, goes to unfortunate waste by the pat, semi-earned finale that gives moviegoers what they (or we) want rather than what they (or we) need.

Headland crams Sleeping With Other People with R-rated frankness and bluntness about sex, commitment, and modern dating (e.g., hook-up culture, technological distractions, etc.), albeit among people of the affluent, Caucasian persuasion.

When we meet Brie and Sudeikis’ characters, Lainey and Jake, respectively, they’re unconvincingly playing college students (Sudeikis especially) who meet non-cute in a college dormitory. She’s a hot mess, desperately searching for the teaching assistant she wants to bed while he, alone and lonely, sees a perfect opportunity for a one-night stand, albeit one with the aforementioned truth-telling and awkward tenderness typical of first encounters (they’re both virgins, too). They part ways, only running into each other 12 years later at a sex addicts meeting. He’s just there to score (he’s an inveterate womanizer), while she’s sincere in her attempts to break a self-destructive pattern (she serially cheats with her former teaching assistant turned OB/GYN, in turn ruining any number of relationships with other men).

Rather than jump into bed together, less a mistake given how closely aligned their worldviews and interests are, they decide to remain friends, in large part to sort out their respective tangled lives. In Jake’s case, that means romancing his new boss, Paula (Amanda Peet). Jake owes his small, tech-related fortune to Paula’s company (she brought him and his partner out). While he jokes his way through meetings – he’s nothing if not perpetually non-serious – she tries (and fails) to keep him at arm’s length. A kindergarten teacher with a trust fund (the only way to explain her super-spacious NYC apartment and money non-woes), Lainey decides to go the abstinence route, turning away multiple romantic opportunities and hook-ups, including with the OB/GYN, Matthew (Adam Scott), who treats Lainey purely as an occasional sexual partner and not a long-term one.

. . .if we look more closely, the same old rom-com patterns disappointingly emerge.

Headland crams Sleeping With Other People with R-rated frankness and bluntness about sex, commitment, and modern dating (e.g., hook-up culture, technological distractions, etc.), albeit among people of the affluent, Caucasian persuasion. Minus Brie and Sudeikis’ appeal as actors, both individually and collectively, the overwrought, entitled narcissistic characters at the center of Sleeping With Other People would have resulted in an entirely different film altogether, one without relatable, root-worthy characters (an obvious prerequisite for successful romantic comedies). Luckily for Headland and, by extension, the audience, she chose well, making Lainey and Jake’s superficial, shallow, self-indulgent characters (Jake more than Lainey) and the journey they take together toward self-awareness and self-actualization, with one or two segues into memorable, soon-to-be-classic set pieces (e.g., self-pleasuring fun with a juice bottle, a children’s party mixed with non-legal drugs), more than bearable.

But if we look more closely, the same old rom-com patterns disappointingly emerge. By the end, we, as moviegoers, are dutifully expected to root for Lainey and Jake to walk, arm in arm, into the sunset together, with decades of happy monogamy, not to mention children and one to two pets, in their immediate and long-term future. Headland feints at a different, far more honest ending for Lainey and Jake, one filled with lessons learned and maturity earned, but like Amy Schumer’s Trainwreck, those rom-com tropes and conventions prove impossible to overturn completely. It doesn’t help that Jake’s womanizing comes off as just a shrug-worthy character quirk while Lainey’s obsession with Matthew borders on the neurotic, if not the outright pathological, both surprising and discomfiting given that a woman wrote and directed Sleeping With Other People.