Interview: Leslye Headland – Sleeping with Other People

Talented writer/director Leslye Headland delivered one of the best romantic comedies in recent years, Sleeping with Other People. I spoke with Leslye how personal the film felt, some of her favorite romantic comedies, men and women being friends, and who she’d like to be her best friend.

I was really shocked with your accurate depiction of relationships in Sleeping with Other People. Most romantic comedies fail at that. How did you nail it?

Leslye Headland: I think it’s because I was in a lot of pain, to be honest. I was so lonely and I wanted to introspectively look at what the problem was. What are you actually scared of? I had a couple successful relationships in my mid twenties, but there was a good five years where it was, “Oh, the common denominator is me.” [laughs]. I couldn’t sit around and say, “Oh, it’s the world…” anymore. I must be the problem. If I had to write my female side and my male side, and they had conversations with each other, what would they be? Then I thought about the kind of movie I’d want to watch about this stuff. When I watch a romantic comedy, what don’t I like? The leads are boring or the set pieces are based in really high octane physical comedy like people getting waxed or pooping. It’s not really about stuff I interact with on a daily basis. It’s not very real. I started to think about romantic comedies I was brought up on and they were pretty high concept like Sleepless in Seattle, My Best Friend’s Wedding, or While You Were Sleeping. Those were high concept ideas and had real people who had a personality to them. The characters had, for lack of a better term, real problems – especially the women. In Sleepless in Seattle, Meg Ryan is all set to marry Bill Pullman and then she hears this guy and she feels like, what if this isn’t it? I think every woman can relate to that. Every woman can relate to Julia Roberts’ dilemma of the second someone’s engaged to someone else you say, “Wait! I’m in love with him.” I thought, what if I made a story about two people were totally unlucky in love. Instead of having sex with each other, what if they really got to know each other and actually became intimate? What would that look like? How does intimacy work? At the end of the whole experience I was watching Sleeping with Other People at Sundance, and it was really about me falling in love with myself. I think that’s why it’s so authentic. It all comes from a very personal place. Sovochek (Adam Scott) is a real person, well like three people. Paula (Amanda Peet) is a real person I know. And I’m Jake, and also Lainey. I’m not trying to be falsely modest, but so much of it is the chemistry between Jason Sudeikis and Alison Brie. A rom-com doesn’t work without it. Even if it’s a great movie, you’re thinking, “Wow, these people have no chemistry.”

And it wasn’t just the comedy where it worked. It was the scenes that weren’t comedic where their chemistry really shined.

LH: That’s all them.

I read a book once that talked about how there’s something in us that connects us to other people. It talked about the idea that you can meet someone for the first time and hit-it-off with that person. We can’t quantify what that is, but it’s a very real thing.

LH: Yes. I also think the alternative to that, and the characters talk about it in the film, and it’s that love is a choice. There is that feeling that you have for someone but you have to make the decision to keep being with that person. That’s why I think most of my romantic relationships fizzled out. I would be extremely attracted to people and anywhere between three weeks and six months later you think, “Who is this person?” [laughs]

You see that with Lainey…

LH: Exactly. She’s attracted to these real magical qualities in this guy. She does have a little sexual anorexia, but she’s attaching these magical qualities to keep herself from being intimate. For the same reasons Jake is sleeping with a bunch of women and throwing them under the bus after. A different version of that, one that you don’t see on film, is someone that has a way of trying to control their sex life and they find themselves in the “other woman” or “other man” territory. Somebody said once, “When you’re having sex with someone in a relationship, you’re having sex with their whole relationship.” Lainey is making herself unavailable. The way we were going in and making those scenes with Adam, it felt like we were making a sexual thriller. We wanted these scenes to sort of just drop in…

Adam Scott turned around and I thought, “This just got really creepy.”

LH: [laughs] I’m so happy to hear that.

SWOP poster

The movie reminded me of another book I read that talked about ideas and how the idea of something is a lot more appealing than actually doing the work. The idea of a relationship is much easier than having to miss football to go meet someone’s grandmother.

LH: Relationships are compromise. This is what I learned about myself, I was choosing to be alone. Yes I was unlucky, and yes I did some stupid things, but ultimately I was choosing to keep myself separate from the world. I was choosing not to show my partners my true self. I was choosing not to compromise. I would say, “F**k this! I’m a famous director and I don’t need this shit!”  I just wasn’t willing to be vulnerable, compromise, or show all of myself to someone. That’s really what Jake and Lainey end up doing. That’s the goal. Instead of love or sex the goal is a weird sense of intimacy. “I love you for free” becomes their credo. It isn’t really about the labels, I just love you. I’m letting go of the control and letting go of the shame.

We were just talking outside about the idea of men and women being friends. You see in the film, that it’s a choice as well.

LH: Michael is my best guy friend and definitely the guy I went out with and people would think we were a couple. If you look at us, we’re having a great time connecting and having the best time. Ultimately we both knew why we were just friends. I thought it would make a good movie. A movie that talked about what the perception is versus the reality of dating. The perception being a big budget studio films make where love magically shows up, “Here he is!” [laughs] No thanks. The reality is that it’s so much more complicated than that.

I wanted to thank you for casting Jason Mantzoukas. He’s so good.

LH: I knew him socially and I wanted to cast him. He’s the guy at the party you just can’t stop listening to. When we were casting for Xander I wanted the person I’d want to be my best friend and that’s Jason Mantzoukas. I really want him to be my best friend. He’s not, but I’m still working on it.

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