Writer-director Leslye Headland’s Sleeping With Other People is the second romantic comedy in recent months (following Trainwreck) that sets out to reinvent the genre only to succumb to all of the same old formulas, serving up the clichés of the form without managing to deliver any of its satisfactions. Sleeping With Other People is a better movie than Trainwreck—at its best it cuts deeper, and it doesn’t have anything as embarrassing as Trainwreck’s bizarre final musical number or misplaced celebrity cameos—but in a way that makes its failures all the more obvious. It comes so close to being a good movie that Headland’s constant tonal missteps become not only dispiriting but downright irritating. She constantly sets up opportunities she then squanders before the audience’s very eyes.
The movie opens with a prologue in which we meet Lainey (Alison Brie) and Jake (Jason Sudeikis), a pair of college students who lose their virginity to each other and then lose touch. Twelve years later, Jake is a serial womanizer (allegedly—like many other things we’re supposed to take on faith via the dialogue, we don’t actually see much of this in action) and Lainey finds it impossible to avoid cheating on her current boyfriend (Adam Brody) with her now engaged ex (Adam Scott). Lainey and Jake run into each other when they attend a meeting for sex addicts, a clunky sequence that unfortunately sets the tone for most of what is to come.
The notion of sex addicts falling in love is a promising one for a romantic comedy—so promising, in fact, that another, far better movie, 2013’s Thanks for Sharing already beat Headland to it. In that film, sex addiction is an integral component of the characters, leading to both hilarious and devastatingly sad scenes in which the condition gets in their way. In Sleeping With Other People it’s just a gimmick, a way of getting around the difficulty of creating viable obstacles for lovers in a contemporary romantic comedy. Virtually the minute the idea is introduced it’s dropped. We never buy that either of these characters actually are sex addicts or would even be at the meeting; it’s just a way for Headland to create a meet-cute scene in an unusual setting.
Herein lies my issue with this film and two of Headland’s earlier works, Bachelorette and the About Last Night remake, which she co-wrote: She’s always willing to forgo careful characterization in favor of a cheap laugh or easy effect. That might be okay if the cheap laughs were funnier, but the comedy in Sleeping With Other People is agonizingly strained; characters constantly drop intrusive pop culture references or do things that make no sense for the sake of a laugh, but the laughs never come because they’re not motivated by anything. To be fair, what Headland is up to here requires a tricky balance, because I’m sure that defenders of the film would say what I see as inconsistent sloppiness is in fact an expression of the messiness and complexity of contemporary relationships, and that real people (and some of the most interesting movie characters) often act against their own self-interest. Fair enough. But there’s a difference between messy, contradictory characters and incoherent filmmaking, and Sleeping With Other People doesn’t have the sense of craft to pull off what it’s attempting.
What Headland seems to be going for is the kind of combination of laugh-out-loud comedy and genuine poignancy that Blake Edwards and Paul Mazursky used to excel at, or that Nicole Holofcener and Noah Baumbach have mastered in their recent work. There’s no reason a movie can’t contain both the broad humor and the painful moments of emotional nakedness that Sleeping With Other People tries to combine—the aforementioned filmmakers did it over and over again. But Headland doesn’t have their patience or care; instead of following through on the implications of her ideas, she constantly cops out and goes for the obvious. After all of the movie’s straining to establish an edgy, modern rom-com premise, it settles into what it really is, a half-baked When Harry Met Sally retread.
Again, I’d even be okay with that if it was a decent retread; the problem is that Sleeping With Other People thinks it’s smarter than it is and condescends to movies that are in fact far superior. (It’s to When Harry Met Sally what When Harry Met Sally was to Annie Hall.) Headland isn’t going to fall for all of the old clichés, but she doesn’t offer up anything in their place; there are occasional moments of truth, but they’re not connected to each other in any meaningful way—they feel like islands unto themselves. If the idea is for the movie to be a truly unconventional look at contemporary relationships, the conceit fails because Headland doesn’t have the courage of her convictions; she still, in the movie’s final act, goes straight for the formula. It’s like trying to be John Cassavetes and Nora Ephron in the same movie, and it doesn’t work.
For all of Headland’s attempts to make this a “real world” comedy, she runs from the real world every time it gets too complicated; a late-in-the-game subplot involving Jake’s romance with his boss (Amanda Peet) sets up all kinds of intriguing practical complications (not only emotional but financial, since Jake is dependent on her for his livelihood), but Headland dumps them all in favor of a pat resolution that audiences would have seen coming 50 years ago. It turns out she wants us to believe in all the fantasies after all—but she’s spent so much screen time acting superior to them that by the time they arrive, we don’t believe in them any more.
Director: Leslye Headland
Writer: Leslye Headland
Starring: Jason Sudeikis, Alison Brie, Adam Scott, Amanda Peet
Release Date: September 11, 2015
Jim Hemphill is the writer and director of the award-winning film The Trouble with the Truth, starring Lea Thompson and John Shea. He has written about movies for Filmmaker Magazine, Film Comment and many other publications. You can follow him on Twitter.