Leslye Headland Explores One-Night Stands' Lasting Impressions in New Play 'The Layover' (Q&A)

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Leslye Headland

The 'Bachelorette' and 'Sleeping With Other People' scribe tells THR of revamping 'Strangers on a Train' for the off-Broadway show and penning a new movie about marriage.

Leslye Headland’s upcoming nuptials have her looking back at her past.

“I’ve definitely had one-night stands or brief affairs that I forget about, but then, suddenly, I’ll remember,” the writer of Bachelorette and Sleeping With Other People tells The Hollywood Reporter. “I wondered why — if it didn’t mean anything, then why do I still have this psychic connection to that person?”

It’s one of the questions posed in The Layover, Headland’s new one-act play that stars Annie Parisse and Adam Rothenberg as Shellie and Dex, who meet during a delayed layover flight on a snowy Thanksgiving night. The off-Broadway production — her third collaboration with director Trip Cullman — runs through Sept. 18 at Second Stage’s Tony Kiser Theatre in New York City.

Ahead of the dark comedy's Aug. 25 opening, The Hollywood Reporter speaks with Headland about her endless fascination with intimacy, her next film exploring marriage and why the upbeat Sleeping With Other People works as a companion piece to this “twisted, weird play.”

What inspired The Layover?

I had been trying to figure out a way to redo Strangers on a Train, one of my favorite books and movies, but couldn’t quite figure out whether it’d be as a movie or a play. Then I had an idea to do a romantic version, as opposed to a thriller. That probably came from my personal life because I’ve definitely had one-night stands or brief affairs that I forget about, but then suddenly I’ll remember. I wondered why — if it didn’t mean anything, then why do I still have this psychic connection to that person? It doesn’t really not mean anything. [Like in Strangers on a Train,] is there really ever no motive? Is there an authenticity to the version of myself I’m presenting in a one-night stand, even though it’s different than what I’d show to] a partner?

How did you craft the characters of Shellie and Dex?

I always want to keep people a little off-balance about what’s going to happen next. So much of the noir genre is about the woman being distrustful — they’re proper femme fatales. I also often inject my own emotional feelings into my male characters to see if it works. I just don’t have the experience of being a man and don’t quite understand the male emotional landscape, so I’m always interested in if a male character will be able to contain my feelings and the things I have in my head.


Annie Parisse and Adam Rothenberg in 'The Layover.' Photo credit: Joan Marcus

What do you hope audiences take away from this show?

This play is the dark flip side of Sleeping With Other People; it basically explores everything I couldn’t in a romantic comedy. I’d like people to take away a lot of the same themes, but without the hopeful, optimistic ending. What constitutes intimacy? That [movie] was a couple who didn’t have sex but were intimate, and here’s one who only has sex. Does that count as intimacy? A lot of our culture would say no — just because you sleep with someone doesn’t mean you’re connected. That’s true, but sometimes, there’s a glitch in the matrix, and sometimes, you are haunted by a person, and something deep and authentic does happen between you and a stranger. In the way that Sleeping With Other People was comforting — yes, you can find love in a Tinder generation — this twisted, weird play is more of a cautionary tale and a dark meditation on that view of casual intimacy.

Have you ever reconnected with a one-night-stand?

I don’t think I have the guts to do that, quite honestly. There’s an intuition for me that says, if an old romance is dead, it should stay dead. Jim Jarmusch’s Broken Flowers, that’s my own personal nightmare. I’d never want to go back. No, thank you. And to me, the memory of a person is a lot more interesting than the reality. I’m getting married next month, so I’m going through that [lookback] of all the old loves, and there are people I’ve romanticized or villainized. Luckily, as a writer, I can just put it all in the play.

So now that you’re getting married, will future projects explore these topics within marriage?

Absolutely. I’m collaborating with another writer on a spec script right now for a movie about a married couple. It’s a thriller, and it’s all about those different nooks and crannies within intimacy. Regardless of what my status is, it’s always going to be extremely interesting to me, how human beings get intimate with each other, what constitutes intimacy and what ties people together. Is it matrimony? We just did our marriage license stuff — does this mean anything? While I’m sure my personal experience will color my work moving forward, you can expect the same bad behavior. But it’s usually the people I don’t know that I’m inspired by. The people who know me actually have less to worry about than the people who interact with me very briefly — so watch out.

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