Leslye Headland & Reviving the Rom-Com

Sleeping with Other People tries to resuscitate a genre left for dead by the end of foreplay

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In 2012, Leslye Headland shocked and delighted with her debut feature, Bachelorette (an adaptation of her own Off Broadway play). The film follows three petty bridesmaids who ruin their friend’s wedding dress the night before the big day and spend one coke-fueled night trying to fix it. After a few years out of the director’s chair, Headland’s back with Sleeping with Other People, a sexier, more realistic take on the traditional rom-com.

The film begins with Lainey (Community’s Alison Brie) banging on Matthew Sobvechik’s (Adam Scott) door, demanding that he sleep with her. When a dorm supervisor tries to kick her out, Jake (Jason Sudeikis) comes to the rescue. The two exchange a few witty remarks and then have sex on an old, creaky couch. Twelve years later, Lainey is addicted to sex—not with her boyfriend (Adam Brody), but with Matthew, her soon-to-be-married OBGYN. Meanwhile, Jake’s sleeping with whomever he can, whenever he feels like it. After reconnecting at a sex addiction support group, Lainey and Jake agree to be friends. But just friends.

Recently, Paste spoke with Headland about love, sex, masturbation and the death (and rebirth?) of romantic comedy.

Paste: Why did you make a romantic comedy about sex addicts?
Leslye Headland: I have a guy friend, and we have this very … odd intimacy with each other, where we both have the same level of depression, I think. And dysfunction. So we [were hanging out], but we weren’t romantic or anything like that. We didn’t fuck each other. It just never came up.

One of our favorite things to do was make fun of couples. Whenever we’d pass a couple or if we were out having brunch we’d make fun of people, and one day it occurred to me that, Oh my god. People think we’re a couple. I know it seems so obvious, and I think that’s what people may think about these characters [in Sleeping with Other People]. Like, “Well obviously you guys are a couple because of this that and the other thing.”

I just started thinking about how it would make a good movie. But they already made that movie, it’s called When Harry Met Sally. Still, I thought, Well, I’ve had a lot of problems dating people and falling in love, so maybe I should write a movie that gives a vocabulary for emotional intelligence. I didn’t really see that in any movies. And it ended up being a romantic comedy. I think it could’ve been any sort of [genre]; it just ended up being funny.

Paste: Why did you want to have a woman character who is addicted to sex? There are a lot of double standards around women who sleep with lots of partners. You address that when Adam Brody’s character says, “You’re not an addict. You’re a whore.”
Headland: Yeah. I also always thought that whenever I saw a female character in a film having sexual dysfunction, or what men consider to be promiscuity—like Silver Linings Playbook, for example, which is a great movie and it was a movie that we referenced a lot, but her “sexual dysfunction” was so surface-level to me. It was like, “She fucked a bunch of people!” “She’s bisexual!” “She’s going through stuff!” I was like, “Yeah, I guess so,” but I don’t know if I really relate with that as a woman.

What I was interested in [exploring with Lainey was] ... what’s actually dangerous? What’s actually scary, where you’re like, “I think I might be alone because I’m obsessed with someone who does not fucking care about me. I’m in love with someone who literally doesn’t care if I return his texts or not. I’m in a position where I need help.”

A big inspiration for this movie was The Apartment. As much as it’s When Harry Met Sally, the set up of it, the actual characters are very much inspired by Jack Lemmon and Shirley MacLaine in The Apartment. In the film, Shirley MacLaine is having an affair with her married boss, and Jack Lemmon, he’s sort of like the character of Jake—he’s sort of a douchebag but … a lovable douchebag. And through their platonic relationship with each other, they end up filling in the moral blank spaces for each other. And then they of course fall in love and so on and so forth.

If I’d just had a hard-talking chick who fucked a bunch of people, I thought, I don’t know if that’s really what’s scary about the dating world right now. What’s scary about the dating world right now is that sex has become so devalued in the dating process. The low point of [Sleeping with Other People] is when [Jake and Lainey] fuck each other.

Whether we like it or not, everything is different now. So, for me, it’s very important that they never have sex with each other and that the audience actually understands without me having them fuck—well they fuck at the beginning of the movie, but that’s sort of like an old-timey rom com trope. Like in 20th Century and The Philadelphia Story, they’re always divorced so that their sexual tension is palpable and you think, It’s okay for them to have [sex] because they’ve already fucked each other. So that’s why I had them fuck at the beginning, so that you weren’t like, “But he doesn’t know what her pussy looks like!” He does, she knows what his dick looks like. They’ve seen each other upside down; it’s fine. Get that out of the way—but it’s a choice. And it gets brought up at the sex addiction meeting. What [the therapist] says is that, “Love is not a feeling, it’s a decision.” What they’re coming to terms with is that the feeling that they get is not necessarily indicative of some sort of action that they should take. Of course, they love each other. Of course, they’re attracted to each other. Of course, they forge this intimacy out of their shared moral bankruptcy. But to actually make that leap to “We should be together” is not that much of a foregone conclusion. It’s something you do have to choose to do. You have to do that. You have to make that choice and decide whether or not that’s the kind of relationship you’re going to have.

Paste: Let’s discuss the sex scenes in the film.
Headland: Sex in romantic comedy is usually either a joke or a reward. That’s not what sex is like in today’s dating land. It’s actually some weird sort of combination of the two. I wanted to sort of throw [the sex scenes in there], like plug them into the romantic comedy and go, “Can you have a romantic comedy that’s actually sexy?”

Paste: The scenes are completely different from what we’re used to seeing in romantic comedies. They’re intimate; they’re sad. We see Jake’s face when he orgasms, which we never see in a romantic comedy.
Headland: Oh, you never see that.

Paste: Lainey teaches a new boyfriend how to pleasure her (after Jake teaches Lainey to masturbate). These are things that we never see on screen. Did you go into the film with the goal of showing sex in a more realistic way?
Headland: Yes. First of all, what you called out about seeing [Jake] orgasm, when I was shooting that scene I was so proud of Jason. I know that sounds ridiculous, but, he and I actually talked through exactly what was going to happen. I mean it’s so bland, that’s what’s so funny, too. We talked about each moment of him cumming; it was planned out. It’s not like he was just making a joke, which is what the male orgasm is. The male orgasm [in film is treated as] a joke. He got so vulnerable to do that… and it’s a huge payoff.

And then there’s [Jake] talking about “The Dirty DJ.” That’s another thing. Is it super realistic that a man is teaching a woman how to masturbate? I don’t know. I’ve gotten in arguments with people about this. I think there are some women [who] become addicted to certain people and certain types of sexual activity because they’re not pleasing themselves in a way that makes sense. Because they’re not encouraged to masturbate at a younger age, I think there are more women who become sexually anorexic and then act out sexually in order to please themselves.

Regardless, I did think it was important that a straight man talk about the vagina. Whereas women are expected to take on male personas when they are sexual, men are supposed to not talk about sex. Them talking about sex is sort of gross. Most of the time in comedies you see men not getting sex and talking about how they’re not getting sex. They’re almost oddly feminized in a weird way, if you want to use that word. Even in When Harry Met Sally, it’s like he’s going through a divorce and yeah he’s talked about how he’s fucking this chick or that chick, but he’s sort of like an emasculated character. Harry feels like a safe guy for Sally to be around. For me, it was just as important that my male character be almost vociferously sexual and overly sexualized. And that he would be talking very openly about the clitoris and the cervix and then talking about 69ing with some chick. Can we do that and can he still be likable and fun and somebody that you want to have sex with?

Paste: I want to add one comment about the masturbation scene, because everybody’s talking about it. I think it highlighted the fact that a lot of women don’t really know their bodies that well or how to make their bodies work for them. When I was talking to my friend about the scene, she said, “I knew men masturbated for almost a decade before I even considered it was something that I could do.”
Headland: Yes! Thank you for saying that.

Paste:This girl’s about to go to med school, yet doesn’t know how to masturbate.
Headland: Right! That was sort of my point. I guess as a good “feminist” I should have a female character that represents a certain enlightenment. But for me, as a good feminist—and it was exactly how I felt about Bachelorette—I actually think it was my job to portray my experience as a woman as truthfully as I can. I’ve had arguments with women about this, too. You know, women who are like, “I don’t know a single woman who doesn’t masturbate.” And then I have conversations with women who are like, “Yeah”—just like your friend—“I spent 10 years not masturbating.” I personally was one of those people. I knew how my body worked, but I still didn’t do it. I was afraid to do it.

Literally the only reason the clitoris is there is for sexual satisfaction. There’s no other reason for it except to be stimulated and for female orgasms. The fact that men haven’t even bothered to figure out where it is is crazy to me. It’s not just our job to figure it out. So to put that on screen and to make it sexy, make it fun—it’s something to energize young male audience members, or old [men], any [man]. It’s not that scary. There isn’t this huge mystery around it. It’s just anatomy.


Paste: Let’s talk about rom-coms. The genre depends on certain tropes. There have to be some messy characters; they have to have some sort of obstacle to face to be together. I’ve read in some interviews that you want to reinvent these tropes.
Headland: Basically, the romantic comedy is 90 minutes of foreplay, right? So the question is: can you make a romantic comedy when no one has foreplay anymore? That’s why I think [the genre] died. I think it’s one of the reasons that it died. I mean I have some other ideas that involve the Farrelly Brothers and basically the turn that the romantic comedy made toward just comedy, and also how Pretty Woman ruined everything. That’s another thing. But ultimately, I do believe in the symbiosis between the audience and the art they consume. I think that part of the problem is that there’s no foreplay anymore. People fuck each other the day they meet.

Sex is something that’s just become less and less of an obstacle. Since that’s essentially what you’re watching when you’re watching 90 minutes of a romantic comedy, that’s one of the reasons that I think the genre ended up becoming a bit outdated. Because, whether or not they wanted to say it out loud, everyone was thinking, I don’t understand why they don’t just fuck each other. It’s not that big of a deal. It’s not that big of a deal. But the problem is that once they do fuck each other, then you don’t have any more obstacles. You see that with the [Elizabeth] Meriwether film, No Strings Attached, and with Will Gluck’s film, Friends With Benefits. It becomes difficult to backtrack and make emotional intimacy a fun thing to watch develop. It’s actually super painful to become emotionally intimate with someone because it means vulnerability; it means honesty. So that was the goal of Sleeping with Other People. Could we make intimacy funny and interesting and have enough realism that it captures that bittersweet feeling of becoming emotionally attached to someone?

[My director of photography] was like, “Why do you always end your movies with a wedding?” And I was like, “Do you know who else ends with a wedding? Shakespeare, motherfucker.”

That’s how you end something! You end it with somebody dying or you end it with a fucking wedding. That’s how it goes. To me, what’s actually more important is your third act. What happens in your third act? How do you get there? You know they’re going to get together. When you watch The Apartment, you know they’re going to get together. Everyone has always known that these two people are going to end up together. That’s the whole premise of it. What’s happened is people got lazy. People got lazy about how they got together and they stopped reflecting on what was actually going on in the world.

Paste: I feel like it’s an exciting time for the romantic comedy though, and it’s largely films by women that are leading the way. Bachelorette had some very romantic elements. So did Obvious Child. Trainwreck is the most recent example of the traditional rom-com with a twist, and now we have your film. Do you feel that women are bringing a new perspective, or at least a unique or interesting perspective to these stories that have become, as you say, lazy?
Headland: I do agree that the more female characters that are on screen, the more female protagonists, the more that you’re going to have women behind the screen, whether they’re writing or directing. It’s not to say that women can’t make male-centric stories—they can. They’re just not allowed to make them. If I go pitch Spider-Man, even if I’m pitching Amy Pascal, she’s going to be like, “No thank you.” So I think this resurgence comes from women feeling like they need to create their own material.

Roger Corman, one of my filmmaking heroes, said that the hardest genre is comedy. Most of the films you’re describing, whether they’re straight up comedies, or comedies with romantic elements, or proper rom-coms, I think women are out there to really prove themselves within that arena because it’s the hardest arena to compete in. I think the idea is, if they succeed there, we’ll be seeing female protagonists in other genres, as well. If you can see success in the consumer-based culture that we live in—that movie made money, women went to go see that, men went to go see that, it was created by a woman, it’s starring a woman—whether it’s a big budget film or a tiny indie, [if it’s successful], more people will say, “Oh, okay. I think I might actually hire a woman to do this job. I might hire a woman to direct something that I wouldn’t necessarily have hired her to direct before.”

Paste: Mid-budget films aren’t getting made as much as they used to. And women directors, as you said, aren’t getting these Spider-Man jobs, so they’re either existing in the indie world or fighting for the same limited dollars to make a mid-budget comedy and that comedy has to kill it critically or at the box office for anyone to notice.
Headland: You’re absolutely right. The comedy genre doesn’t involve a lot of set pieces and isn’t as expensive, in the sense that you don’t need to have someone hanging from a building, or you don’t need to CGI. You can actually justify getting a mid-level budget for a film that might push some buttons, or might be funny and sort of not funny, might star some people who are cool but aren’t bona fide movie stars. There’s Alison Brie, who is someone who I’ve always, always loved, and always wanted to work with. It was like pulling teeth getting her cast. Because it’s like we have to justify, especially as female filmmakers, the money that we’re spending. If they can’t pre-sell the entire thing, based on who’s in it, then I don’t get to make my movie.

Paste: I have to ask you about the ACLU petition. There’s been a lot of press recently about the lack of diversity in Hollywood. Do you think this increased focus is actually going to lead to a change? In your experience as a woman writer and director, what’s your assessment of the situation?
Headland: My personal feeling on it is that somebody needs to intervene. I think that at some point, you’re going to have to just tell people that 30% of their directors are going to have to be women, or 30% of their writers, or even 50% if you can get it to there. But we’re at like 9% right now, with no change in the last 50 years.

Paste: Less than that!
Headland: It’s horrible. So unless there’s some sort of [mandate], like “You have to do this”, no one’s going to do it. There’s no reason to.

Paste: Tell me about your next project. It’s with Cosmo, right?
Headland: Oh, that actually got passed on. NBC didn’t pick that up. I was really excited by it, too. I really loved working with [Cosmopolitan Editor in Chief] Joanna Coles and the producers on it. It was really fun to write that script and develop those characters with them, but NBC didn’t pick it up. I’m writing a couple of television projects now, none of which are really at a place to have a log-line. They’re just sort of there and on the horizon. And I’m writing a thriller—that’s my next [thing]. I’m writing a thriller about a newly married couple who commit a murder together. We’ll see what changing genre does. Knowing me, it will probably still end up being funny.


Regan Reid is a Toronto-based freelance writer. You can follow her on Twitter.