Film Review: Sleeping with Other People

by Carrie Kahn on September 18, 2015

When Jake met Lainey: Headland’s smart, funny rom-com worth seeing

Lainey (Alison Brie) and Jake (Jason Sudeikis) discuss their relationship status over Ben & Jerry’s.

If you don’t like romantic comedies, you might as well stop reading right now, since Leslye Headland’s new film Sleeping with Other People is, without a doubt, a bona fide rom-com. But, if you are open to the category, then you’re in for a real treat here – Headland’s film is smart, funny, and true, and one of the best and brightest pictures the genre has seen in years.

Having likable leads with terrific, palpable chemistry of course helps, and Headland should send her casting director roses and chocolates for finding Jason Sudeikis and Alison Brie for the film’s starring roles. Both are attractive in an “I could have gone to high school with them” kind of way, and both are charming and fearless comedians. In Headland’s story (she both directed and wrote the film), Sudeikis’s Jake and Brie’s Lainey meet as college freshmen at Columbia, and decide to lose their virginity to each other. After that brief opening coda, the film fast forwards 12 years, and we find the two unexpectedly running into each other at a sex addiction meeting, neither having had much romantic success post-college. Jake is a serial dater with commitment issues, and Lainey can’t stop sabotaging relationships by cheating with her old college crush Matthew (an inspired Adam Scott, cast against type as a dull, humorless doctor). Given Jake and Lainey’s history and their present issues, the pair decides to form a strictly platonic friendship (although, of course, they come up with a safe word to use in case either starts feeling sexual tension; their selection of the word is one of the movie’s funniest bits).

Jake (Jason Sudeikis) and Lainey (Alison Brie) make the most of attending a kid’s birthday party.

What follows, then, is basically an updated version of Nora Ephron’s 1989 classic When Harry Met Sally, replete with Natasha Lyon in a Carrie Fisher-esque role as Lainey’s best friend, who flat out echoes Ephron’s film, telling Lainey that “men and women can’t be friends.” And Lainey and Jake, in one of several modern touches, are even shown on split-screen, texting each other, instead of talking on the phone, à la WHMS’s Billy Crystal and Meg Ryan.

But despite the similarities between the two pictures, Headland’s film easily stands on its own; it’s really less derivative of the earlier film, and more of a loving homage to it. In fact, Headland’s reverence for the great comedies – romantic or otherwise – shines through here, and her picture features lots of playful, winking nods to the likes of Annie Hall, Manhattan, Casablanca, and, in what is perhaps the film’s funniest and best inside joke, The Graduate (suffice to say that Lainey’s real name is actually Elaine).

What helps the film immensely, of course, especially when compared to other romantic comedies, is that it hardly ever feels false. In fact, Lainey’s obsession with Matthew, a married, stiff, unlikable (except to her, of course) cad, is presented with a searing honesty that is rare in comedic films. The truth of Lainey’s situation will be achingly real to anyone who has ever had intense, unrequited feelings for someone who is unavailable and unworthy. Headland’s sharp writing elicits the best kind of empathy and compassion from her audience.

Jake (Jason Sudeikis, right) expresses his displeasure with Matthew (Adam Scott) when they unexpectedly run into each other.

But that’s not to say the movie doesn’t have plenty of laugh-out-loud moments; it absolutely does. A scene in which Jake instructs Lainey on, shall we say, a particularly intimate matter using an ice tea bottle is bound to become as classic as Meg Ryan’s Katz’s Deli table-pounding scene. And all the supporting players are stand-outs. In addition to the very funny Lyonne, Jason Mantzoukas as Jake’s friend and business partner Xander gets off some the film’s cleverest lines, and Adam Brody and Amanda Peet are game in smaller, but pivotal roles.

But, ultimately, the picture belongs to Sudeikis and Brie, and they prove themselves more than up to the task of carrying the film with their warm, nuanced, and deftly comic performances. With romantic comedies, you know the ending going in, so the reason to watch is to see how the characters will get there. Headland and company don’t disappoint in that regard. Getting there isn’t just half the fun here; it’s 100% of it.


Sleeping with Other People opens today at Bay Area theaters.

Carrie Kahn

Moving from the arthouse to the multiplex with grace, ease, and only the occasional eye roll. Proud new member of the San Francisco Film Critics Circle.

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