College student Jake (Jason Sudeikis, "Horrible Bosses," "We're the Millers") comes to the aid of Lainey (Alison Brie, TV's 'Community,' 'Mad Men'), a distraught young woman about to be thrown out of his dorm. He can't believe she's obsessed with Matthew (Adam Scott, TV's 'Parks and Recreation,' "The Overnight"), a guy he deems the most boring guy on campus. The two lose their virginity to each other on a rooftop, but when Jake awakens Lainey's gone and he won't see her again for twelve years, when they meet outside a sex addiction workshop as they've each had problems "Sleeping With Other People."
Since its Sundance debut, writer/director Leslye Headland's ("Bachelorette," 2014's "About Last Night") latest has been described as a raunchy "When Harry Met Sally." If only. While it's nice to see Sudeikis stretch from his usual comedic roles into something more heartfelt and real, the film frequently makes no sense. Even worse, it's not funny. I'd have much rather watched a movie about supporting characters Xander (Jason Mantzoukas, "The Dictator," "Adult Beginners") and Naomi (Andrea Savage, "Step Brothers," Showtime's 'Episodes') whose marriage is refreshingly modern and whose closing credit roll banter is better than most of what has come before it.
It's difficult to ascertain why Lainey views herself a sex addict as twelve years after first meeting Jake she's still obsessed with Matthew, a prig of a doctor she meets up with frequently (the attraction is a problem, the only indication we get for Lainey's obsession a late coming verbal recollection of his lovemaking). Jake is one of those guys who'll sleep with as many women as possible. The two go down that old road of agreeing not to have sex with each other because they always lose sexual partners, even though their chemistry is unmistakable. Their mutual support gets Lainey back on an educational path while Jake finally commits to his lovely single mom boss Paula (Amanda Peet, "2012," "The Way Way Back").
In addition to the closing credits, there are exactly three good scenes in the entire film. When Jake discovers Lainey's never had an orgasm, even on her own, he teaches her the 'dirty DJ' using an empty iced green tea bottle. Later, hopped up on E before a birthday party for Xander and Naomi's child, kindergarten teacher Lainey takes control of the unruly kids by leading them in an inappropriate dance lesson to Bowie's 'Modern Love,' a song used before for dance expression in better films. The two actors also share a touching moment as they declare their love for each other - as friends - in a scene that features Headland's best writing ('I love you for free').
But that's far from enough to sustain a film that goes exactly where we expect it too, without even finding a soft landing for an unfairly treated romantic partner (as romantic comedies generally do). The film employs Natasha Lyonne ("But I'm a Cheerleader," Netflix's 'Orange Is the New Black') as Lainey's sounding board Kara without giving her anything to do. Sleeping would be a far better use of time than "Sleeping With Other People."
Robin gives "Sleeping With Other People" a D+.
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