Sleeping with Other People: Serial cheaters, a love story

What happens when a female ‘love addict’ becomes close friends with a ladies man averse to commitment?

Serial cheaters, a love story

Leslye Headland has a message for men: start talking honestly about sex.

“I think most men are scared to talk about sex frankly, scared to be anything besides a lothario or a jokester about it,” she says.

Perhaps this is why her new film, Sleeping With Other People, has the leading man, Jake, played by Jason Sudeikis, giving a tutorial on female pleasure to his romantic foil, Lainey, played by Alison Brie.

The scene is awkward, hilarious and touching, and fits perfectly in a film that is candid about sex, the modern dating landscape and the dynamics of contemporary relationships.

Headland, 33, a screenwriter and director from Connecticut, says she can’t help but write about sex. She isn’t trying to be provocative; she just thinks that sex and relationships are among the most interesting things we experience as humans.

Her writing simultaneously exposes, dismantles, demystifies and glorifies sex, partially in the hope that her ­viewers may start talking about it more openly.

“I made this film as much for men as I did for women,” she says, “so I wanted to show an example of a straight guy talking about sex very frankly and not being a creep about it.”

At its core, Sleeping With Other People is a story about two people, disposed to self-sabotage, who fall in love with each other and try not to act on it. So convinced of their need to remain just friends they even create a ­sexual tension safe word — “mousetrap” — that’s sure to ruin the mood.

Lainey suffers from a “love addiction” that urges her to constantly cheat on her boyfriend Sam, played by Adam Brodey, and Jake is a ladies man who resorts to cheating on all of his ­girlfriends to avoid the all-too-­difficult “it’s not you, it’s me” ­conversation.

Jake and Lainey are unlikable characters from a moral point of view, but Headland, who wrote and directed the film, wants the audience to recognise that this doesn’t make them any less worthy of love. “Sure, they’re flawed, but who isn’t?” she asks.

A great deal of Headland’s experience informs her work and she creates characters such as Jake and Lainey to explore her feelings.

“I just feel like the version of life that I experience is too dark and upsetting, and so I basically create little dioramas or films for these characters to populate so that it’s easier for me to deal with things, like the fact that I might be alone forever.”

Faced with the challenge of portraying such fractured characters on screen, she made sure her script was in the hands of a capable cast that ­radiates rom-com chemistry and comedic timing.

“They all came from a very honest and authentic place as well as me,” she says.

Sleeping With Other People is an ode to and a critique of the romantic comedies that precede it. Traditional conventions are subverted from the outset: romantic leads typically don’t meet until a few scenes in, but Jake and Lainey meet and take each other’s virginity in the opening scene.

Sly allusions to films such as Casablanca and When Harry Met Sally also feature throughout, making for a game of “spot the reference” while confirming the film’s rom-com heritage.

“I don’t really try to re-create anything, start a new genre or overly subvert anything,” she says. “Instead I like to lean on traditional set-ups so that I can slip in things that are a little less traditional.” Here this involves taking drugs at a kid’s birthday party, attending sex addicts anonymous meetings and openly discussing female genitalia.

By including things that don’t typically belong, Headland says she hopes audi­ences will be “more inclined to go along with the harder truths of the story” and ask themselves questions “like why do we have sex with people we don’t like, and why do we keep relationships going even when we know they’re not good for us?”

Headland is also a playwright. She previously has written a cycle of plays based on the seven deadly sins — she has written six of them so far, one of which formed the basis of her previous feature, Bachelorette, a film about gluttony, starring Rebel Wilson and Kirsten Dunst. She is working on another play, one she labels ­“regular, run of the mill”, called Layover.

When asked about how differently she approaches theatre and film, she likens the process of theatre to blowing up a balloon and film to swimming in a butterfly event at the Olympics. “With a play,” she says, “you do it little by little and with each day, each rehearsal it changes shape and becomes different and then suddenly you wrap it up, let it go and never see it again. Whereas with film you’re just breathing and moving and breathing and moving, and then when you’re done you lift your head up and you go, ‘What was my time?’

“You’re so submerged in the process of making the film that it’s ­really about endurance and strength rather than really sitting back and contemplating what you’re looking at.”

So now, as Headland lifts her own head out of the water, awaiting the judgment of audiences, all she knows is that she will be satisfied if her film gets even one more man talking frankly about sex.

“Men can make funny jokes about their dicks and talk about how many women they’ve f..ked with their buddies, but to really talk about sex and what that means, I’d like to see more of that.”

Sleeping With Other People opens nationally tomorrow.

This weekend in Review: Stephen Romei assesses Sleeping With Other People.