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Sleeping With Other People

Sleeping With Other People poster

Directed by Leslye Headland

(1st January UK – Gloria Sanchez Productions, IM Global, Sidney Kimmel Entertainment)

Written by Leslye Headland
Starring: Alison Brie, Jason Sudeikis & Adam Scott
Synopsis: A good-natured womanizer and a serial cheater form a platonic relationship that helps reform them in ways, while a mutual attraction sets in.

Taken on face value, you’d be forgiven for giving Sleeping With Other People a wide berth. A seemingly generic romantic comedy starring Jason Sudeikis and Alison Brie is not an inspiring prospect on paper, but it’s the involvement of firebrand writer/director Leslye Headland that makes this worth consideration. Headland received ample critical praise for her 2012 film Bachelorette, but it unfortunately was overshadowed by Paul Feig‘s widely successful, similarly-themed Bridesmaids which came out just the year before. Bachelorette was not only raunchier, but also a lot smarter. Alas, it was never really given the same shot at mainstream acceptance that Bridesmaids was, and so it was back to the drawing board for the passionate young filmmaker. Now she returns with a decidedly more emotional project but not one without its flaws.

Sleeping With Other People starts simply enough with our leads in their college dorms back in 2002. Lainey (Brie) is making a scene because her older teaching assistant Matthew (a barely recognisable Adam Scott) won’t take her virginity (the spectre that looms over the entire film). Jake (Sudeikis) prevents the hysterical young girl from being thrown out of the dormitory and the bond between the two is formed after mocking her for wanting to have sex with the weird Matthew, he admits that he too is a virgin. Naturally, they aren’t virgins at the end of the night, but they also never see each other again – until the present day.

In 2015, each of them get a separate scene highlighting their respective dysfunctional and problematic relationships. Jake is a womaniser that struggles to remain faithful, and Lainey is still obsessed with (the oddly unsettling) Matthew, now a successful married gynecologist, with whom she is having an affair. They fall back into each other’s lives when Jake spots her at a sex addiction meeting; a place he traditionally frequents for hook-ups.

Ultimately, because they both struggle with commitment and sex in their relationships, they decide to become best friends, and essentially perform all the respective parts of a strong relationship, minus the act of bumping uglies. Unlike past romantic comedies that have taken a similar tact, Sleeping With Other People largely manages to avoid contrivances, and instead takes the time to build their relationship in a wholly organic way. The pair have superb chemistry, which carries the film over many of its shortcomings, and as an audience we actually get to see them authentically fall in love, which is a rare, and emotionally satisfying sight for a romantic comedy.

Sleeping With Other People Jason Sudeikis Alison Brie image 2

While the romantic chemistry is a definite highlight, the film fails to deliver on its promise of hilarious comedy. Clearly, the minds of our leads work in fascinating ways, as their exchanges are peppered with a number of references and quickfire quipping that would make most other comedies of the genre envious, but none of them are individually funny enough to elicit anything other than amusement. With her script, Headland casts a wide net, discussing everything from Aaron Sorkin‘s cocaine habit, to Malcolm Gladwell-ian logic jumps, to gaslighting and sliding scales of morality, but it’s just not sharp enough to prove as incisive as the material thinks it is.

Of course, it being a Headland film there’s a few raunchy moments sprinkled in for good measure. Jake and Lainey attend a children’s birthday party high on ecstasy and the latter proceeds to lead the children in an inappropriately sensual dance. Normally this is when outraged parents kick up a fuss, but in a unique twist, they’re all refreshingly liberal and find the whole thing largely amusing (with one dad even using his son to hit on Lainey in the aftermath, and the hosts of the party lamenting about how much fun taking drugs used to be). There’s another standout scene where Jake violates an empty green tea jar to leach Lainey the best way to masturbate, in a sequence that goes surprisingly vivid in its descriptions, but it’s actually used as another tender moment as the bungee cord that represents their sexual attraction to one another continues to fluctuate, before they pull away from one another, out of fear of ruining what they have.

Outside of their titular dalliances with other people, this is the form that their relationship takes throughout. Early on, they coin a catchphrase “Mousetrap!” which one of them must say if they ever think they’re getting too close to one another. So, we’re treated to multiple scenes where the two look like the perfect couple, that get closer, and closer, until suddenly “Mousetrap!” snaps them back to reality. It’s an engaging idea, and one that creates a sense of anticipation among the audience, because they will find themselves waiting for the catchphrase to fail, or not be uttered in time. If anything, within the central relationship, Sleeping With Other People shows a remarkable restraint, which in turn enhances their chemistry with one another.

There are some concerning elements at play though. For one, sex addiction plays a role in the early stages of the film, but is promptly dispensed with. It becomes clear that neither of our main characters actually suffer from a true addiction to sex, just impulse control issues. The problem with suggesting that our leads have addiction issues is that it does a disservice to the many people that actually do suffer from the condition. Unlike drug and alcohol dependence, sex addiction is still not a widely accepted problem, and so while we’ve had a few incredible films about it (such as Steve McQueen‘s Shame), Sleeping With Other People falls back onto the lazy stereotype of merely mocking it. Also, Jake has a complicated relationship with his female boss at work, a successful single mother, where he doggedly pursues her, ignoring her rejections, and ultimately using his position at the company as uncomfortable and irresponsible power play leverage, starting their relationship on a morally questionable dynamic. These may seem like minor grievances, but they seem particularly out of place in a film that otherwise goes out of its way to prove that it has a smart and socially aware head on its shoulders.

Sleeping With Other People Jason Sudeikis Alison Brie image

At least, until the final act, where the whole film falls apart in a confounding way and squanders much of the goodwill it had thus far generated. Suffering from “too many endings syndrome”, Sleeping With Other People transforms from a realistic but bittersweet ending into a poorly-judged violent altercation that exposes Jake as a selfish, destructive asshole. For him to then go on to get the “true happy ending” feels not only cheap and contrived, but wholly unjustified.

Traditionally, in dysfunctional romantic comedies our leads start off as conventionally ‘bad’ people, but then slowly become more socially acceptable so that they ‘deserve’ the happy ending. Here, the reverse happens, and it makes it impossible to root for Jake’s happiness as a result.

It’s a shame that Sleeping With Other People‘s final moments squander a lot of what has come before, because there is still plenty to fall in love with. Sudeikis and Brie’s extremely naturalistic performances and witty banter make a refreshing pair of leads for a familiarly-structured but independently-spirited romantic comedy, and there are some wonderfully quirky turns from a game supporting cast.

Ultimately, it’s a film that due to its lack of outright hilarity works better as a strong, relatively amusing relationship drama than a superlative romantic comedy. Headland imbues Sleeping With Other People with her trademark confidence and style, but the film loses its way by the end, and feels like a victim to its own hubris, not recognising when it has structurally gone too far and subsequently alienated most of its audience. In that way, it’s largely unique considering that romantic comedies are usually harmless crowd pleasers, but it’s the sort of individuality that only hurts the final product. Feeling like it gets caught in its own mousetrap in the concluding moments, Sleeping With Other People tries its best to make something original and compelling out of a tired genre, but it’s the conventionally mandated, unearned feel-good ending that squanders much of the film’s potential, resulting in a feeling of hollowness, and a massive missed opportunity.


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