Interview: Director Leslye Headland Tries ‘Sleeping with Other People’

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CHICAGO – Leslye Headland is facing the new era head on, by putting a post modern Harry-met-Sally spin on her new film, “Sleeping with Other People.” Her question is how do people connect in the new age of hook-ups and online options? Jason Sudeikis and Alison Brie portray the couple trying to answer that question.

Leslye Headland came out of Connecticut, and graduated from the Tisch School of the Arts at New York University in 2002. She worked for four years as an assistant for producer Harvey Weinstein, and first gained notice as a playwright. One of her plays, “Bachelorette” (2012) became her first writing and directing effort in film. She adapted the screenplay for the remake of “About Last Night” in 2014, and premiered “Sleeping with Other People” at the Sundance Film Festival earlier this year.

Alison Brie, Sudeikis and Director Leslye Headland On the Set in ‘Sleeping with Other People’
Photo credit: IFC Films

HollywoodChicago.com spoke to Ms. Headland via phone, as she explained her film, a modern take on coupling in the 21st Century.

HollywoodChicago.com: What did you observe about relationships, either in your generation or other friends, that spurred the idea for this screenplay?

Leslye Headland: Whenever people I know would talk about going on a date – or whatever the variation of dates are these days – it always seemed to come down to texts or phone apps. I observed that people were getting high of the idea that they could love someone, rather than actually loving someone. There was sex, but no emotional intimacy. If you are doing that, and just relying on texting to get to know someone, then they can become whoever you want in your head.

For example in the film, the Adam Scott character was just texting and having sex with Alison Brie’s character. But she was having a whole other relationship in her head, and didn’t want anything else out of it, why would she? That was her deal. So what kept coming up for me is the question of does love even exist in such a landscape? And that’s how the friendship angle came up with the Jason Sudeikis and Alison characters. They weren’t pretending to be other people.

HollywoodChicago.com: How does the character of New York City influence the characters in your screenplay?

Headland: I live here, I like it here, and I can’t manage to leave for some reason. One of the things I talked about with my production designer and director of photography before we started the film, was about assigning each of the characters a different neighborhood, whether they live there or not. We didn’t want to set it in one particular place, like Brooklyn, we stayed in Manhattan as much as possible. We tried to make those neighborhoods influence each scene, as opposed to really thinking about it realistically.

HollywoodChicago.com: What, in your opinion, makes the type of relationship that Elaine and Jake healthier, in the process that it went through, rather than someone who goes through the usual hook-up, relationship, engagement and marriage?

Headland: Because the gap between meeting someone and hooking up has gotten so small, people are getting physically, and sometimes emotionally, involved with other people without knowing them. It takes several months to actually know somebody, to observe them in real life with family, friends and their reactions to things.

I’m not dissing modern sex lives, but emotional intimacy can follow physical intimacy very quickly, and if that happens with someone you don’t know, then it’s interesting to see where that might lead you. The cool thing about Jake and Lainey is that they do get to know each other, their ups, downs and how they live in the world, and do they still like each other? They respect each other not to have sex when it presents itself, and they take it easy. It might behoove some people to try that.

Alison Brie and Jason Sudeikis Have a Casual Moment in ‘Sleeping with Other People’
Photo credit: IFC Films

HollywoodChicago.com: You filmed some sex scenes, and in the age of the internet, everybody has to remain in some kind of clothing. Do you ever think the American film industry will ever get over its relative modesty when it comes to depicting sex on screen, or will it just get more clothed? Also, how difficult is it to choreograph a sex scene?

Headland: The choreography was a bit difficult, so I storyboarded those scenes and rehearsed them many times, even down to when certain clothing would come off. There was no improvisation in those scenes. As far as nudity goes, I’d always planned to not show anything. I come from theater, where people get naked all the time, and in college people were always putting nudity in their shows to be cool. Whenever I watched these, I would just think of the actor, and not the character. That’s why I wanted as little nudity as possible.

HollywoodChicago.com: How about America’s cultural dealings with nudity?

Headland: I think the industry has no problem objectifying women, or seeing them naked or getting raped, which you see on a regular basis on television crime dramas. We need to see more dick, I’d love to see more dick, and I’d also like to see women enjoying sex more on screen. That is another problem. In conclusion, there are certain standards the industry is okay about, and others that they’re not.

HollywoodChicago.com: There is an ongoing debate in the movie business about the difficulties that woman have getting their films made and their voices heard. Do you have an example of an obstacle you had to overcome in your career, and what is the most sexist thing you’ve ever heard or experienced in the business?

Headland: I don’t know if we have time for the most sexist thing. [laughs] But I will say that female filmmakers, on average, get lower distribution deals. That was very difficult on both of my films, getting the distribution that I wanted. That never occurred to me, that it would happen to me as a female writer and director, that the attitude would be that I’m ‘happy’ with a certain situation.

For example, I wanted to push for a certain infiltration into the marketplace, and the push back was ‘don’t ask for more.’ – the point was I should be happy that they want it at all. I just think there is room to negotiate, and I am very happy with how IFC has handled the film. That’s why it took a little more time to sell it at Sundance.

HollywoodChicago.com: What can you tell us about Harvey Weinstein that the rest of the world doesn’t know?

Headland: He wears sweatpants more often than you would think. [laughs] He very much believes in being comfortable.

By PATRICK McDONALD Writer, Editorial Coordinator HollywoodChicago.com pat@hollywoodchicago.com