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Review: Sleeping With Other People Wants to be the When Harry Met Sally for the Oversexed Generation

Sleeping With Other People has been jokingly summed up as starring Jason Sudeikis and Alison Brie as “two garbage people who fall in love.” That seems like a particular specialty of writer-director Leslye Headland, a former Harvey Weinstein assistant who made a name for herself as a playwright before adapting one of her plays into the Bridesmaids-esque comedy Bachelorette.  It was supposed to be the next big thing until people saw it at Sundance in 2012 and realized how little they cared for the three main characters (played by Kirsten Dunst, Lizzy Caplan and Isla Fisher) who endure a bachelorette party gone horribly wrong on the eve of their friend’s (Rebel Wilson) wedding.

Aside from a screenwriting stint on 2014’s About Last Night, Sleeping With Other People is Headland’s follow-up project, and she has thrown her proverbial hat into the ring of filmmakers attempting to put their own spin on When Harry Met Sally. In fact, while on the promotional trail Headland frequently referred to Sleeping With Other People as “When Harry Met Sally, but with assholes.”

The basic story is similar. A guy (Jake, played by Sudeikis) and a girl (Lainey, played by Brie) in college share a moment together before parting ways, forever as far as they’re concerned. Years later, they improbably run into each other again, surprised to discover they are both at the same basic station in their lives. Instead of pursuing a romance together, they agree to be friends, quickly forming an emotional bond which they fear would be ruined by sex. Along the way, they have several frank conversations about the differing male and female perspectives on relationships and sex, sometimes in person, other times over the phone (or, in this case, via text). At one point, one member of the duo teaches the other member an invaluable lesson about the female orgasm. When they each finally get separate spouses things get complicated. You have a sneaking suspicion that it’s all heading toward some kind of grand, romantic gesture.

To be fair, it’s not exactly like When Harry Met Sally has exclusive authorship over the “Can a guy and a girl just be friends?” story, but it is now the consistent cinematic reference point. In recent years, there have been multiple efforts in the indie realm to update the story for the modern generation since the rules of courtship have become infinitely more complex, yet also simpler than ever (swipe left or right to find your true love on Tinder).

daniel-radcliffe-what-ifThe title which immediately comes to mind is Michael Dowse’s 2013 rom-com What If with Daniel Radcliffe as a med-school dropout burned by love and unwilling to be anything more than friends with the cute new girl he meets (Zoe Kazan), who happens to already have a boyfriend anyway. Oddly enough, Sleeping With Other People also has a med-school dropout in its central pair, although this time it’s the girl, not the guy.

Headland’s new angle on the material is to layer a story about sex addiction over the familiar When Harry Met Sally narrative.  Jake and Lainey actually lose their virginity to each other in college, and when they find each other again it’s because they are both attending a self-help group for sex addicts.  By that point in the movie, we’ve already seen Lainey break her sensitive boyfriend’s (Adam Brody) heart by admitting her rampant infidelities, and we’ve seen Jake try and fail to talk his way out of being punished for sleeping with his girlfriend’s sister.

Lainey responds to the emotional turmoil by closing down and immediately texting a booty call to put off dealing with her feelings whereas Jake cracks jokes and quickly moves on to flirting with his new boss (Amanda Peet). When Jake and Lainey fall back into each other’s lives, they outwardly state that maybe they can help each other learn how to just be friends with the opposite sex. In practice, it feels like Jake is Lainey’s sex addicts sponsor, helping her from relapsing back into the arms of the quirky, married Doctor (Adam Scott) who’s clearly using her.

Sleeping With Other PeopleSudeikis and Brie have an easygoing chemistry together, which is important since a movie like this rests entirely on the believability of its central duo. For example, if you can’t get behind Radcliffe and Kazan as friends on the verge of becoming something more then What If won’t hold together for you. In the case of Sleeping With Other People, Brie and Sudeikis don’t necessarily make for an implausible pair, although the obvious 7-year age difference doesn’t help. It’s more that Brie appears to actually be trying to create a character while Sudeikis is mostly running through an aggressively confident, motormouth bravado before taking a stab at emotional growth in the final act. It feels too much like schtick, even if that’s the point.

That being said, Lainey and Jake’s occasional negotiations over the politics of their friendship (e.g., Is it weird if he takes a date to what is more or less “their restaurant”?) feel emotionally honest, and Headland tries very hard to subvert rom-com cliches, e.g., the couple has sex in the first scene, Lainey’s cliched giver-of-advice best friend happens to be a rather proud lesbian (Nathasa Lyonne), etc. There is arguably more drama on display than comedy, although it doesn’t go quite as dark with its depiction of sex addiction as the 2012 Mark Ruffalo-Gwyneth Paltrow dramedy Thanks For Sharing.

thanks-for-sharingFor the supporting cast, there is an odd “Who’s Who” of the indie comedy scene feel to most of it, with Andrea Savage and Jason Mantzoukas easily emerging as the funniest part of the movie. Even the comedy centerpiece of the film’s trailer – Jake and Lainey getting high before attending the birthday party of a friend’s young son – is upstaged by Savage and Mantzoukas’ likely improv-driven one-liners, fondly (and not so fondly) recalling their prior drug experiences.

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Savage and Mantzoukas riff for several minutes over the closing credits, and it’s arguably the most purely funny moment in the entire film

It ultimately feels like Sleeping With Other People is trapped between two poles, a sweet-natured romantic comedy on the one side (like What If) and an indie-leaning examination of sex addiction (like Thanks For Sharing) on the other. It ultimately tips toward the former in the end, arguably to its detriment, but my personal fondness for the performers involved made up for it.  If you are, however, not already a fan of Brie or Sudeikis or Mantzoukas then Sleeping With Other People might have a limited appeal.

THE BOTTOM LINE

Sleeping With Other People doesn’t completely work, but there are flashes of honest and entertaining observations on the current state of romance, even though the serious drama doesn’t always hold up well next to the rom-com shenanigans.

CRITICAL CONSENSUS

63% – “Sleeping with Other People has likable leads and flashes of inspiration, but seems unwilling or unable to surround them with the truly subversive rom-com they deserve.”

THE TRAILER

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About Kelly Konda (1853 Articles)
Grew up obsessing over movies and TV shows. Worked in a video store. Minored in film at college because my college didn't offer a film major. Worked in academia for a while. Have been freelance writing and running this blog since 2013.

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