Interview: ‘Sleeping With Other People’ Writer/director Leslye Headland

Only a true media professional opens an interview with a question as perfect as Daniel Rutledge does here. One outlet’s loss is Fliks’ gain – and yours – as he’s joined in conversation by Sleeping With Other People director Leslye Headland about her raunchy, Jason Sudeikis and Alison Brie-starring sorta-rom-com.

FLIKS: YOU’VE DESCRIBED THIS FILM AS “WHEN HARRY MET SALLY FOR ASSHOLES”. WHAT DO YOU THINK MAKES THE MAIN CHARACTERS ASSHOLES?

LESLYE HEADLAND: Well, I meant that the audience were the assholes!

OH I’M SORRY, I MISUNDERSTOOD!

Yeah, when I pitched it, I meant people who don’t like romantic comedies normally would like this romantic comedy. But I do think that Jake [Jason Sudeikis] and Lainey [Alison Brie] are struggling with being honest in their lives, not that that makes them assholes. They’re struggling with their own self acceptance, insecurities, gender roles; they’re not getting to know people before they have sex with them, they’re sort of having sex in the dark and trying to figure it out what they want. They’re a bit wayward, but I don’t think they’re assholes. I think if you ask Jason and Ali, they would say they’re not assholes!

COME TO THINK OF IT, AT ONE POINT IN THE FILM LAINEY ACTUALLY SAYS HERSELF, “I’M NOT AN ASSHOLE”.

Oh yes that’s right. That was right out of my own life, that scene. I had this guy who I was sleeping with, who was involved with somebody else. He was sort of in between people, you know what I mean? He was sort of setting me up, it was just weird. He was like, ‘Why are you ignoring me? Why aren’t you replying to me?’ and I told him, ‘Because I’m not a fuckin’ asshole, man!’ I fell for you and I’m part of it, but I’m not just going to keep recklessly hurting people I don’t know. I couldn’t pretend it wasn’t happening or wasn’t affecting me.

What’s cool about Jake and Lainey, they have consciences, even if they’re not listening to them. They know right from wrong, but they feel they’ve gone so far off the deep end of being lovable that they can’t come back. Their relationship with each other starts to heal that.

 YOUR FIRST FILM ‘BACHELORETTE’ CAME OUT IN 2012 AND NOW ‘SLEEPING WITH OTHER PEOPLE’ IS ABOUT TO BE RELEASED. WHAT HAPPENED AFTER ‘BACHELORETTE’ THAT INSPIRED YOU FOR THE NEW FILM?

I guess my life sort of fell apart, haha! My boyfriend and I broke up, I worked on a television pilot that didn’t end up going, and the network tied me up for like a year so I couldn’t work on anything else. I was in this weird dichotomy of being at film festivals with my first film, which I had worked my whole life to do, but everything else turned to shit. So when I was looking at what project I should do next, I think I was wanting to do something to cheer myself up a bit. I started writing honestly and authentically about how I felt about being alone and being lonely.

But then when I finished the script and started doing pre-production, as I realised we were making a rom-com, I started to lean into how fun the movie was and how we could explore these different ideas, different aspects of modern dating; and I started to have a really good time doing that. It really helped me get out of that hole. When I watch the end of the film now, with two characters kissing, I see it as me falling in love with myself and making peace with myself. I realised I am a lovable person and not a failure.

THIS FILM IS COMING OUT THE SAME YEAR AS ‘TRAINWRECK’, WHICH I THINK HAS A LEAD FEMALE CHARACTER WHO IS SIMILAR TO LAINEY, IN TERMS OF HER SEX LIFE. THESE HONEST PORTRAYALS OF MODERN WOMEN ARE UNFORTUNATELY NOT ONES WE’VE NOT SEEN OFTEN BEFORE. WHY DO YOU THINK WE CAN FINALLY SEE THESE SORTS OF FEMALE LEADS ON SCREEN, WHAT’S CHANGED?

I don’t think anything has changed, honestly. Everyone still doesn’t like those characters, even if they are showing up in the cultural zeitgeist. The main reason my film wasn’t made by a studio was because of Alison [Brie]‘s character. Just because it’s a trend doesn’t mean it’s accepted. I think if I had a friend who was behaving in the way Ali’s character does they’d feel really bad – even if Amy Schumer made a really good movie, I think she’d still feel bad.

BUT HOPEFULLY THESE FILMS ARE AT LEAST STEPS IN THE RIGHT DIRECTION.

I hope so. I think those things are generational though. I think we might know a little bit more about the effect these types of female characters have on the landscape when today’s kids grow up.

 THERE’S A DRUG SCENE IN THIS FILM, AS THERE IS IN QUITE A FEW MODERN COMEDIES, BUT THIS ONE INVOLVES ECSTASY AND CHILDREN, AND IT’S DONE IN A PRETTY NONCHALANT WAY. DO YOU THINK THAT SCENE SHOCKED SOME PEOPLE?

It never occurred to me that it would be shocking, does that make me terrible? It’s like the bottle scene, where Jake teaches Lainey how to masturbate, that didn’t seem shocking to me either. It wasn’t until I was watching it with an audience, hearing people react to it, when I realised, ‘Oh God’. To me it was sort of ideological or satirical. I don’t think of those scenes as realistic.

The bad guy in this movie is shame, the idea that what you do sexually defines you and if you feel bad about what you’ve done, you don’t deserve to be loved. So I wanted to put the characters into a scene where there would be no shame. The only time I felt like that was when I was a little kid. So I thought I’d put them around a bunch of kids, but they’re still not going to feel lack of shame unless we alter their chemistry in some way. So I wanted them to be kids again, to take them back to before they saw their body as a bad thing.

I think that’s where I get into trouble as a filmmaker, people go ‘You can’t do that! You can’t say that! It’s not realistic, people don’t behave this way!’ I’m not doing these things to be realistic or to effect someone’s moral compass, I’m trying to get to a feeling. In this scene it’s a feeling of before we started judging people. It never occurred to me until I started having my work published that this could upset people. All of my heroes – David Mamet, Woody Allen, Stanley Kubrick, John Cassavetes – I saw them do it over and over so I didn’t think much of it. Then I heard, ‘How dare you talk about blow jobs!’ and I was like ‘What the fuck?’ I don’t know, I don’t understand why I can’t show things like that.

WHAT ADVICE WOULD YOU GIVE PEOPLE WHO ARE STRUGGLING TO FIND LOVE DESPITE HAVING BASICALLY UNLIMITED SEX ON TAP?

I think you should get to know somebody before you have sex with them. I think that’s the number one mistake people make, especially women. I think they see sex as a way of getting to know someone. It’s not a moral thing, just etiquette-wise, try getting to know somebody before you invite them into your house. I know women and men that have sex with people they wouldn’t want to have coffee with. They just fuck because they guess they’re supposed to, or think it’s their God-given right as a feminist, but no – do you actually like this person? Is it someone you want to spend time with? Do you know anything about them?

So yeah, that’s what I would say to my girlfriends who are struggling with dating and stuff. I ask if they actually like him, and if they go ‘Oh I don’t know, but in bed he’s great’. It’s one of the reasons I shot the sex scenes in the film the way I did, sex is almost another character in the movie. It’s not a joke and it’s not just a way to get to know somebody, it’s a mysterious, interesting thing. Biologically, it’s creation – you’re creating something, even if it’s not a baby, you’re creating a connection with somebody. So why make that connection if you don’t actually like the person? It doesn’t make sense to me. So I’m actually a prude, deep down, after all of the shocking things I said!

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