Director and screenwriter Leslye Headland talks ‘Sleeping with Other People,’ “fake sex” scenes and our addiction to happy endings

Leslye Headland is making her name one people will recognize. In 2012, she made her directorial debut with Bachelorette, starring Kirsten Dunst, Rebel Wilson, and James Marsden among many other well-known actors. She also wrote the 2014 romantic comedy remake About Last Night that starred Kevin Hart, Micheal Ealy, and Regina Hall. And now she’s back writing and directing her new film Sleeping with Other People, starring Jason Sudeikis and Alison Brie.

The romantic comedy follows Lainey (Alison Brie) and Jake (Jason Sudeikis), who lost their virginity to each other and reconnect years later. Lainey can’t seem to get over Matthew (Adam Scott) and Jake is a womanizer who can’t really commit. With their own issues notwithstanding, the two of them decide to become friends, with the promise that everything remain platonic that helps them reform their ways.

Leslye Headland took the time out of her busy schedule to talk to me about the film, romantic comedies and their “fake sex” scenes and why we’re so drawn to happy endings.

You can read the entire interview below! Sleeping with Other People is out now in select theaters. You can read my review of the film here.

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I saw the movie a couple of weeks ago and thought it was very inspired by “When Harry Met Sally.” What were your other influences behind the movie? 

I think in one of the ways it’s unique from When Harry Met Sally is that Jake and Lainey aren’t under any assumptions that they are going to be friends. They say they should be friends, but I think they know that they’re not going to. I think the question for them is whether they can draw sexual and emotional boundaries with someone, which they haven’t been able to do with anybody else in their lives. And that differs from the movies where they’re like, “maybe we can be friends and fuck each other,” even though I like those. Like Friends with Benefits…. And it’s not [in Sleeping with Other People] just about their relationship, but how they are changing for the better, which is what love is sort of all about, you know?

And I think people always want to be friends before they enter into a relationship, even though that’s definitely not always the case. 

Oh, absolutely! I think there’s something lost in translation now that everyone is just f***ing each other. Sort of a big difference between now and then. You know in When Harry Met Sally, they don’t have sex until the beginning of the third act, now people don’t go on dates. They don’t actually get to know each other, they just find each other on Tinder or a dating app and they go out to a dinner or a movie and then they fuck each other. So they’re immediately physically intimate with each other and so the question I wanted to ask myself personally was, can I make a believable romantic comedy about two people falling in love and have it be believably romantic? Ultimately the idea isn’t to tear down the genre, but to actually say…. It’s a romcom with 90 minutes of foreplay. How do you make a romcom for a generation who has no idea what foreplay is?

That’s what I did like about the film, the fact that there’s a buildup, whereas a lot of romantic comedies have them falling in love over the course of a few days. 

Oh good, I’m glad. And that also came from the title Sleeping with Other People. Because it was a title I came up with in college. It was a title where you could use that phrase in so many different ways. You could use it when you’re in a relationship, when you’re out of a relationship. The idea that characters would be having active sex outside of what they’re doing… outside of the people they’re supposed to be with.

Both your movies have the romantic comedy aspect and the exploration of the relationship between the opposite sex. What about this genre compels you to write for it?

I think the most compelling part is that you have to have a happy ending. You don’t have to, like (500) Days of Summer doesn’t. But one of the hardest things about the genre is that it does need to end happily, even if they don’t end up together. And like I mentioned with (500) Days of Summer, she [Zoe Deschanel] ends up married while the main character [Joseph Gordon-Levitt] ends up alone, there is still an ending where there is someone and they introduce Autumn and Julia Roberts ends up with her gay best friend. But I think for us, because it is a love story and it is specifically a love story where the two do fall in love with each other, it was very difficult to work from the backwards end. Knowing they would end up with each other and knowing that the audience was pretty sure they were going to end up with each other, then what kind of movie are you going to make? I think that’s the hardest and the most important part of a romantic comedy is the happy ending. It’s just all that stuff in between, what are you going to do? [laughs]The genre is so based in that.

Image from the movie "sleeping with other people"

Adam Scott’s character though, is very distant and aloof. It was interesting that Alison Brie kept going back to him over and over again even though she kept getting hurt. What’s the story behind her inability to move on from that?

That’s just from my personal experience. Right before I wrote this movie, there was a guy and it was off and on. We were just always fucking, and then when we were in different relationships we stopped, then we’d break up and then we’d fuck each other again. He was just sort of this constant in my life. I wasn’t as hung up on him as Lainey [Alison Brie], but I had that experience. And most of my friends were really… it was very hard for them to give me support because they’re real enough to say, “He’s horrible. Horrible!” And in the film, he’s [Adam Scott] a doctor and there’s all the different role plays that they do. He’s the doctor, she’s the patient; he’s on top, she’s on the bottom. She wanted to lose her virginity to him. At some point she decided to give him a lot of power, and more than that, that’s what she finds sexy. It’s actually nothing about his appearance, which is one of the reasons why we wanted to highlight the fact that this person just, arbitrarily almost, gave this person a lot of power over her, and she’s turned on by it and she’s compelled by it, but it is an illusion. And it’s an illusion she just needs to wake up from. And sometimes those things are very hard to wake up from.

What inspired the bottle sex scene and why did you want to include it?

Well I wanted to include the scene because every romantic comedy has, essentially, a fake sex scene. They have a scene that’s really chock full of sexual tension and the subtext of it is that you get to imagine the characters having sex with each other and how exciting and funny and cool and sexy that would be. In When Harry Met Sally, it’s when she fakes the orgasm in the deli, which is very funny and she’s making a point about men vs. women which is what the whole movie is about. But at the same time she’s faking an orgasm and he’s reacting to it and so you can subconsciously, or consciously, imagine them having sex with each other. And in Trouble in Paradise, they pick each other’s pockets and at the end they hug, but it’s because they couldn’t show any fucking back then. And so I knew I would have to have one. So I put in the jar scene, well first of all, I used to do that at parties. I’d get drunk and then show the boys how to finger a girl because they didn’t know how and no one talked about it in health class.

And I decided to have Jake {Jason Sudeikis] do it as opposed to Lainey because I do think we’ve seen women explain the vagina to men and I was like, I’d really love to hear a great guy talk about sex. So for me it was much more interesting to have a guy say those things than to hear a woman tell a guy that. And I also thought it would be interesting to have his character teaching her how to rub herself because that’s what she’s doing to him emotionally because she’s teaching him to love himself. There’s just a lot of symbolism. The actual execution of it is something I didn’t think we’d pull off. I was pretty sure we would fuck that up or we’d have to cut it or something. But Jason [Sudeikis] and Alison [Brie] are so brilliant. They just played it like any other scene, that’s the best way I can put it. [laughs]They didn’t get nervous, they just went in and did it. There were other days that were harder than that one for them, I think. And I think we did a good job, all of us.

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About Author

Mae is a Washington, DC-based film critic, entertainment journalist and Weekend Editor at Heroic Hollywood. A member of the Washington, DC Area Film Critics Association (WAFCA), she's a geek who loves discussing movies and TV. She is also a voting member of the Black Reel Awards. If she's not at the movies, she's catching up on her superhero TV-watching, usually with a glass of wine in hand.

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