‘Dating & New York’ Director Talks Dating App Romantic Comedy

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In “Dating & New York,” the film’s central romance isn’t your grandparents’ — or even your parents’ — standard meet cute.

The main characters, single, 20-something New Yorkers Milo (Jaboukie Young-White) and Wendy (Francesca Reale), don’t bump into each other at a bookstore or in the produce section of Trader Joe’s. No, the eventual will-they-or-won’t-they couple become acquainted on a dating app.

“There are so many new rules to the game of modern dating,” says the film’s 30-year-old director Jonah Feingold, who lives in Brooklyn. “Even back when our parents were meeting, it seemed very wholesome, simple. You sat next to each other on an airplane, you were neighbors, you met in law school.”

That’s not the way that many millennials are getting to know one another. A Stanford University study found that nearly half of heterosexual couples met their romantic partner online. It’s a concept Feingold explores in depth in “Dating & New York,” which premieres at Tribeca Film Festival — through the virtual Tribeca at Home — on June 13. Ahead of its festival debut, IFC Films scored rights the movie with plans to release it theatrically and on demand in September.

Jaboukie Young-White, Francesca Reale and Jonah Feingold on the set of “Dating & New York”
Chase Sui Wonders

The movie centers on two young Manhattanites who both swipe right on the fictional app Meet Cute and, in true commitment-averse millennial fashion, don’t initially start a relationship. Instead, they forge a “best friends with benefits” contract for some harmless no-strings-attached fun. “Dating & New York” isn’t based on personal experience; for one, Feingold says he has never drawn up anything formal to establish ground rules for hooking up. But Wendy and Milo’s journey out of singledom is one that may look familiar to many city dwellers.

“I was excited to make a film that their meet cute is quite literally just matching on an app,” Feingold says. “Nothing special. They both swipe right, and that’s how they met.”

At the same time, the internet can lead to stranger-than-fiction unions. Feingold recalls hearing about one long-term couple who met in the comment section of the food website The Infatuation.

“How do you explain that to Nora Ephron or Nancy Meyers? They would be like, ‘What the fuck are you talking about?’ That’s what excites me the most about modern dating,” he says. “It’s kind of hilarious. It’s the Wild West.”

Feingold fell in love with the concept of “happily ever after” as a child after seeing Steven Spielberg’s 1991 fantastical adventure “Hook” starring Robin Williams. “I watched it every single day,” he remembers. “I dressed up as Captain Hook. I mean, my teachers thought I was insane. I instantly knew that making a movie was what I wanted to do.”

His parents introduced him to the catalogue of Nora Ephron and Nancy Meyers, and he was raised on romantic comedies like “When Harry Met Sally” and “The Holiday.” Growing up in Manhattan, he began making home videos featuring his sister, the neighbors, stray dogs, whomever he could convince to get in the shot.

Armed with a fascination about couples’ origin stories, Feingold, a first-time feature filmmaker, had to get scrappy to finance “Dating & New York.” He made what felt like an endless series of calls, pitching anyone who would listen, to raise enough cash to begin shooting independently. By happenstance, he was introduced to the actor Jerry Ferrara, best known to “Entourage” fans as Vincent Chase’s lackey Turtle, who boarded the film as one of its producers, in addition to voicing the narrator and playing Milo’s doorman.

All the while, Feingold began putting together his dream call sheet. That included Jaboukie Young-White, a 26-year-old comedian whose shock humor regularly gets him suspended from Twitter. A correspondent on “The Daily Show,” Young-White landed on Feingold’s radar after his scene-stealing role in the Netflix romantic comedy “Someone Great.” As for Francesca Reale, the 26-year-old elevated her profile with “Stranger Things” Season 3 and the indie comedy “Yes, God, Yes.” Convincing her to join the cast, however, proved to be more difficult because Reale lives in Los Angeles.

“She read the script, and I FaceTimed her from Central Park,” Feingold says. “I was trying to convince her to come to New York. I was like, ‘Look at Central Park, it’s beautiful. Come make a movie here.”

As the title would indicate, the movie gets into the specificity of dating in the city that never sleeps but sleeps around.

“In New York,” Reale says, “the city is such a part of your dating experience. If you break up with someone, you’ll walk down that street and have PTSD.” Young-White says New York amplifies “that super romantic idea that everyone has their soul mate. The bigger the city, the more you feel, ‘Well surely there’s gotta be somebody.’ On one hand it gives you hope, but on the other people start to feel disposable.”

Reale attests she’s not like the Type-A, pragmatist Wendy, and Young-White says that unlike Milo, he doesn’t self-identify as a manic pixie dream boy. Yet the actors were given the freedom to inject their own personalities into their respective roles.

That was put on display in the first lip-lock between Wendy and Milo.

“We didn’t understand the type of kiss that Jonah wanted us to do,” Reale recounts. “We were on a different planet.” Adds Young-White, “In my head, I’m like, ‘OK the date is probably not stopping at this kiss, so it’s going to be passionate.’ And then Jonah was like, ‘Whoa, whoa, let’s tone it down a bit.’ We got to a more sweet kiss, but we were [initially] going for more spicy, steamy.”

Adding to cloudy judgement, Reale had been coming down with a cold. “I had just gotten off a plane, and I started to get sick,” Reale says. “I felt so bad, we had our first big kissing scene and I was fully ill.”

Not to be outdone, Young-White brought his own amount of awkwardness. “Right before that scene, I had a bag of Flamin’ Hot [Cheetos] so you know what… that’s also not fair. We both brought some baggage to that kiss.”

Though stereotypes abound in “Dating & New York” (yes, Feingold jokes, the city itself is the third wheel in their open relationship), the cast and director maintain that there are misconceptions about the generation that’s obsessed with instant gratification and won’t accept anything less than perfect when it comes to their soulmate.

“It’s actually difficult because you don’t have a rulebook to play by,” Young-White says. “It’s not like you can turn to some old book and, like” — he channels an old-timey voice — “‘Well, you go steady and then you put the ring on it.’ You don’t have that anymore.”

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Because of the pandemic, Feingold had to remotely compete his movie

Also without guidelines: how to complete a movie during a world-altering pandemic. Like many crews, that were in production as COVID-19 began to spread, so Feingold and his team had to edit and fine-tune the film remotely. “We were doing test screenings over Zoom,” he says. “It was stressful.”

Already, “Dating & New York” feels like a time capsule. The movie was shot during the fall and winter of 2019, before the pandemic forced the city to mask up. It was a more innocent era, when casual hookups didn’t carry with them the risk of contracting a deadly virus. Still, the age of ghosting and read receipts continues to thrive in the most romantic city in the U.S. Feingold hopes the movie is useful as New York shakes off its COVID slumber and people begin to remove masked photos from their dating app profiles.

“I want people to watch it on a first date or during their Sunday scaries. They can be swiping on Tinder or decompressing from a work week,” Feingold says.

“At Tribeca, it’s coming out on a Sunday, and that’s the perfect time slot. You got your bacon, egg and cheese, your iced coffee and you’re regretting the text you sent the night before,” he adds. “We’re going to be there to help you feel better.”

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