Leslye Headland’s ‘Sleeping With Other People’ surprised even her

Director and writer Leslye Headland's latest film is the anti-rom-com, "Sleeping With Other People."

Director and writer Leslye Headland’s latest film is the anti-rom-com, “Sleeping With Other People.”

(Genaro Molina / Los Angeles Times)

Leslye Headland wears her commitment to filmmaking on her sleeve — or at least on her forearms. One is tattooed with the problem-solving aphorism “What would Lubitsch do?” while the other has a quote from the endearing ‘80s artifact “War Games.”

That mix of classical style with a contemporary twist, knowing when to take things seriously, when to laugh and a boldness to make it all one’s own, makes for a good summation of the mind-set of the writer-director of “Sleeping With Other People,” which opens Friday in Los Angeles.

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Headland’s work bubbles with the energy of right now. In the film, Lainey (Alison Brie) and Jake (Jason Sudeikis) lose their virginity to each other in a college one-night stand. Twelve years later they meet again in New York City when each is at an unusual crossroads.

Lainey is trying to extricate herself from a romantic obsession with the married man with whom she has been having an affair. Jake is a general cad-about-town with a go-to move of cheating as a way to exit relationships. The two of them become friends, emotionally intimate with each other while attempting to avoid anything physical so their past behaviors won’t mess things up.


In many ways a self-conscious inversion of the modern romantic comedy, “Sleeping With Other People” spends much of the story asking the audience to want the central couple to not get together. That is, until the story shifts from being an anti-rom-com to one in which happy endings are desired.

All of which came as something of a shock to Headland.

“I have to say it really didn’t hit me until I watched the assembly,” she said recently, referring to her first time watching the footage of the movie put together. “I called Jessica Elbaum, my producer, and I was like, ‘It’s a rom-com’ and she was like, ‘Yeah, I know.’ And I said, ‘Nobody told me.’

“Once I embraced the fact that it was a rom-com, that’s what it ended up becoming.”

Brie, best known for her roles on TV’s “Mad Men” and “Community,” likewise recognized “Sleeping With Other People” as something different from the first time she had read it.

“I read a ton of rom-coms, and they for the most part feel the same,” Brie said. “The characters are all kind of similar, and you know exactly what’s going to happen, and even the jokes and the timing, the rhythm feels the same. And this script was nothing like that at all; the first time I read it, I didn’t even think of it as a romantic-comedy. I thought, ‘This is a cool indie dramedy about relationships and sex.’ ”

Sudeikis, star of mainstream comedies such as “We’re the Millers,” was attracted to the directness of his part. Jake is a pickup artist who makes no bones about his ability at manipulating situations and emotions to his advantage.

“At least he’s not about looking like a wolf in sheep’s clothing. He is a wolf in wolf’s clothing,” said Sudeikis.

The 34-year-old Headland’s new film is the follow-up to her 2012 debut feature “Bachelorette,” which starred Kirsten Dunst, Lizzie Caplan and Rebel Wilson and was an adaptation of her own stage play. That film is now widely seen as a prototype success for new hybrid models of distribution for independent films, finding an audience largely through video-on-demand.

With its caustic look at female friendship, bad behavior and the culture surrounding weddings, “Bachelorette” seemed to follow in the slipstream of success after the breakthrough “Bridesmaids.” For Headland, that unintended connection proved dispiriting.

“When you sideline somebody’s success, make it part of a trend, it becomes so devastating to the artist, and I think that’s why it became depressing to me,” Headland said. “My film wasn’t respected in and of itself. At the time it just felt like you’re just part of this thing that happens to be happening right now, so enjoy it while it lasts.”

“ ‘Bachelorette’ is not, was not and was never meant to be ‘Bridesmaids,’ ” said Elbaum, producer on both of Headland’s features, “and I think it was misrepresented and in turn misunderstood.”

Noting the summer’s other self-aware take on the romantic comedy, Elbaum added, “For me right now it feels a little similar with ‘Sleeping With Other People’ and ‘Trainwreck.’” It’s like Leslye and I can’t catch a break.”

Simply as a point of comparison, it is, nevertheless, tempting to want to point to voices similar to Headland, who are likewise examining contemporary behavior and relationship dynamics, whether it be “Trainwreck” star and co-writer Amy Schumer, Lena Dunham, Diablo Cody or Ilana Glazer and Abbi Jacobson of “Broad City.”

“I really think she’s her own thing,” said Elbaum. “Leslye comes across as really intense and tough, but she’s just a softie. She’s got the edge and darkness, but she’s also a romantic.”

Brie echoes that sentiment. “It’s still a movie with two characters falling in love. It’s great that Leslye can make a movie that does both of those things, feed the cynic and the romantic at the same time.”

Headland has a few television projects in the works and recently finished a rewrite of a script currently called “The New Neighbors,” a thriller set in a gated community, which she hopes will be the next film she directs.

Addressing the larger issue of barriers to female filmmakers working on projects not typically thought of as being for female audiences, she said, “That’s what I think the problem is, not so much that I’m treated in some different way but that I’m seen as somebody that wouldn’t be interested in that. I’m not even allowed in the room because there’s this idea I will infect it with my feminine-ness and it will be some girlie version of it.”

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