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Interview: Writer-Director Leslye Headland on Sleeping With Other People

sleeping with Other people

Last week, we spoke with Sleeping With Other People’s writer-director Leslye Headland about her new movie … after, of course, bonding over our shared name with spelling reversal which stuck us both as an awesome Black Swan kinda thing (her clever comparison, not mine). But really, we were there to talk about her new movie, which premiered at Sundance this year and is now out in theaters and on-demand. It stars Jason Sudeikis and Alison Brie as 30-somethings who lost their virginity to each other in college and are now suffering from somewhat dysfunctional sex lives. We talked about the importance of making a sex positive comedy, the financial risks of making a sexually active female protagonist and where this film falls in the rom-com timeline.

Lesley Coffin (TMS): I know that almost since the film came out at Sundance, the movie has received a lot of comparisons to When Harry Met Sally. How did you react to those comparisons?

Leslye Headland: To be honest, that was the pitch I made. I described it as When Harry Met Sally for assholes. But that was just the commercial pitch. Really, I wanted to make a romantic comedy for lonely people. I was lonely when I wrote it, and if you watch When Harry Met Sally when you feel like that, it can actually make you feel worse about being alone. I wanted to make a movie that would make people who were alone or felt lonely feel better, because the movie is about how important it is for these characters to learn to love themselves, so they can eventually love each other.

TMS: The movie addresses, and questions, whether Jake or Laney are in fact sex addicts. Did you do research about sex addiction to figure out what the psychology of it is and if either of them would fall into that definition?

Headland: I did, because there really aren’t movies about it that I could draw from. There aren’t romantic comedies where the women have a lot of sexual experiences. What is interesting is how lonely that made Alison’s character, Laney. She can’t talk about it with her boyfriends or even friends, and that isn’t necessarily true of Jake’s character, who is also has a lot of sexual experiences.

TMS: When planning the film, did you consider how differently they might be received, because of that old belief that promiscuous men are playboys but promiscuous women are bad girls?

Headland: Absolutely. In fact, that is the reason this movie isn’t a studio film. I conceived it that way and all these people told me, it feels like a big studio comedy. But the studios said, “she’s too unlikable because she’s been with too many men.” They wanted that cut and her relationship with Adam Scott’s character removed because he is married and they are having an affair. And they didn’t have the same problem with Jason’s character. I find that in a lot of movies, they want female characters to be “likable” or they just want them to act like a guy. And Laney was neither. She is a woman and flawed and sexual. I wanted her to be real, because I wanted to see a character like her on screen.

TMS: Did you base any of Laney on yourself?

Headlnad: Oh, absolutely. But by the time we got around to filming, I found I related more to Jake than I did Laney. Autobiographically, there is a lot of myself in Laney. That obsession with a guy is something I’ve experienced. But personality wise, I realized I’m more like Jake. And I asked Jason, “are you playing me?” and he’s like “yeah, that’s why I did the movie.”

TMS: I’m sure you’ve been asked about this scene a lot, but I just had to ask why in the bottle scene you had Jake teaching Laney about female masturbation, rather than the reverse?

Headland: Well, there is a tradition of sex without sex scenes in romantic comedies, from Trouble in Paradise, with the pick-pocket scene, to the organism scene in When Harry Met Sally. So I wanted to include one of those classic scene. And it is the scene I’ve been asked about the most, which is odd because I thought it would be the scene where they take Molly. I don’t know what I was thinking in hindsight. But I also wanted a scene where a straight man talked about a female vagina and wasn’t just acting dumb.

We’ve had scenes where women talk about their own vagina, and friends talk or instruct. But I wanted a scene where a straight man showed his knowledge of the female anatomy in a sexy scene. But I also think there are more women who don’t masturbate than we think. And that is part of the reason they act like Laney, and become obsessive. Because they don’t know how to masturbate, and even if they do, they don’t feel satisfied because they don’t know how to really love themselves.

TMS: The rom-com has recently gone through this shift into making “anti-romantic comedies” which this film isn’t. It’s raunchy and starts out kind of dark, but ends with a very optimistic view of love. What are your own feelings about rom-coms and that current cynical trend?

Headland: Well, the first rom-coms were sort of about sex without sex. They were mostly about remarriage. But they were always about men and women learning to live together despite their differences. Finding that common ground in a relationship. And it wasn’t until the 80s that we really saw a rise in the Cinderella stories in romantic comedies. And that was also around the time this became a largely female made film genre.

And recently, men have kind of taken it back in the past few years. I think the kind of film you’re talking about really comes from this age of cynicism we’re living in right now. It’s as if we can’t believe men and women can find that compromise anymore, and there is a very clear split between women’s romantic comedies and men’s romantic comedies, which didn’t exist in those early movies I’m talking about. Which is too bad, because I don’t want to just make movies for one gender.

When I made Bachelorette, there was all this talk about it being a movie for women, but really, it appealed to men’s sensibility too. And I want the same thing for this movie.

TMS: Watching the film, I honestly think I would have been just as satisfied if Jake and Laney ended up just friends, because I really like that relationship and seeing that friendship on film. Did you ever consider not having them together in a relationship?

Headland: It’s interesting you say that. When I was filming, some people asked me, maybe it should end with the U-Haul scene. And I just said, that is a different movie. For me, I wrote it from the perspective that this was a romantic comedy and that they would end up together. And while I could have made a movie about a friendship like theirs which ends platonically, that wasn’t what I was interested in making.

I have a male friends who I’ve never had a romantic interest in and I love our relationship. But I also have a boyfriend I love. And those are different relationships. We didn’t need to ask, “Can men and women be friends?” I wanted to ask, “Can men and women still fall in love in this cynical age?”

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