‘Dating & New York’ Director Jonah Feingold Chats About His Debut Indie, Rom-Coms & More [Interview]

In the feature debut of director Jonah Feingold, “Dating & New York,” which premiered at the Tribeca Film Festival earlier this year, the filmmaker makes his attempt at the romantic comedy by way of modern dating practices such as the reliance on apps and how technology has informed and devalued human connection. It’s an ambitious and, at times, messy feature that attempts to both deconstruct and honor the genre he clearly loves. 

READ MORE: ‘Dating & New York’ Plays Like ‘When Harry Met Sally’ For Twenty-Something Millennials [Tribeca Review]

The film follows two twenty-somethings, Milo (Twitter comedian-turned-actor Jaboukie Young-White, who also turns up in “C’mon C’mon”) and Wendy (Francesca Reale), who are both tired of the dating game and the consistent heartache and confusion that comes from it. After meeting up again after their first date, the two decide to come to an agreement where they are given all of the privileges of dating one another without the actual title. It’s friends with benefits with more feelings and commitment but not so much that they become an actual monogamous relationship. Our critic wrote, “Taking advantage of the glories of New York City, Feingold ushers his lovers (and their sidekicks) into shimmering subway stations, onto the sunlit ferry, into cozy ice cream shops, and swanky rooftop bars, and through a rainy but beautiful Central Park, with them bantering all the way.”

We spoke to Feingold about the inherent magic of New York City, collaboration on set, and his time working at Buzzfeed and how it informed his filmmaking. 

Did you have the idea for this script for a while, or was it inspired by a particular moment or interaction or even a person you met?
I was talking to somebody about that. Any particular person did not inspire the film. In this case, it was because I really loved rom-coms growing up. I grew up loving Nora Ephron and Nancy Meyers films all the way back to Billy Wilder and all of those classics. I just hadn’t felt like I’d seen a romantic comedy that made and spoke to the nuances of what our generation was going through, like how to respond to a text message or the significance of being posted on a grid rather than a story on Instagram. Granted, in an indie movie where you’re your own boss when it’s just you and your crew, you can do that. I’m not sure a studio would trust you spending so much time on an “I miss you text.” That was really the inspiration for it. I wanted to get to the minutiae of modern dating that took the classic premise while thinking about how we could make it feel and sound more modern than what we’ve seen on film before. 

The script is definitely derivative of many short films I’d made before making this feature and having worked at Buzzfeed and having that digital era of filmmaking. 

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I’d seen that you’d worked at Buzzfeed and had made videos for other online platforms. I was wondering how much that affects your filmmaking style or if you’re able to separate what you’ve done already and how you’re pursuing it now. Or, as a modern filmmaker, do you need to know how to bridge the two?
Yeah, it’s funny, I was bad at Buzzfeed, and I got fired from Buzzfeed because their note to me was that I was ‘thinking too much like a filmmaker and not as a content maker – this isn’t USC film school, you don’t need to set coverage on how to make grilled cheese in four easy ways.’ I was like, what do you mean, and I couldn’t drop it, and everything I made was elaborate in some capacity. While I don’t think that I ever related to the Buzzfeed style of filmmaking, I did relate to it because we had to do a video and a half a week, and all these different outlets I worked for were like news in that we moved very quickly. That taught me how to be precious when it mattered and when to move quickly and what I wanted to make a movie. We shot this film in fifteen days and when it’s you and your camera that’s very easy to do but when it’s you and a crew it’s not easy. I’d say that experience with digital really helped. I’d also say too many filmmakers – I look back to some of the videos I made in 2015, 2012, 2018 – and whether subconsciously or consciously, there are direct iterations of concepts. Wendy giving a press conference was an Instagram video I made four years ago, and then I decided to put in a script in a bigger way. That’s the beauty of digital work that we get to practice our craft much more frequently and then use those ideas for our bigger hurdles. 

I feel like there’s been a reevaluation of the rom-com genre over the years after people have separated it from the idea of the “chick flick.” What in particular draws you to it, and were there specific ones you grew up with? I believe we’re around the same age, and there wasn’t a weekend that went by where “You’ve Got Mail” wasn’t playing on TV.
Strangely enough, that movie was constantly on TV. Same with “Sleepless in Seattle.” I think many filmmakers will go to film school and want to direct action or thrillers, and since day one, I’ve wanted to go make “Night at the Museum” and “How to Lose a Guy in 10 Days.” That was nice because it helped me find my voice, and there was no real competition—the reason is that rom-coms are fun because they’re still a genre piece. We still know what’s going to happen – they’re going to meet, they’re going to break up, and then get back together in some capacity. This is similar to horror or thriller, and I think the reason I think filmmakers are drawn to the genre is that you get to flex your voice muscles within the constraints of the genre. 

Rom-coms are fun because I get to do a little bit of magical realism – which is what I love, like the magical subway signs and the therapy session on the street. You can have a lot of fun with the music and how you tell the story, but the audience still feels comfortable enough knowing what they’re going to get. In particular, you can be funny. You can have moments of heart, but you can also try and make the audience laugh. That’s why I love a rom-com because you can still do outside of the genre things within that genre. The movies I really loved were obviously “You’ve Got Mail” and “When Harry Met Sally” but also sort of off the beaten path is a film like “L.A. Story” which is a Steve Martin movie and which is the kind of perfect movie in my mind. It’s got the magical billboard; it has the Enya music video that happens halfway through with the rain. It’s cinematic and funny, and calming. I was watching “Muppets Take Manhattan,” which isn’t a rom-com but is a movie that I think is perfect, tonally executed, and sort of still plays with genre as great rom-coms can. Then a movie like “Modern Romance,” which was an Albert Brooks film that I think was very ahead of its time. 

The film has a particular tone with that magical realism you mentioned, and it’s bookended like it’s a fairytale when in reality, it’s a pretty cynical film. Did you always know that was the tone you were trying to achieve, or was it something that built itself organically?
On the pitch deck, the first words were always “dating, a hyper-modern rom-com fairytale.” And I love classical Disney films. I love “Emperors New Groove,” a really obscure reference, but there are some tonal similarities if you watch it recently. I wanted to make it with a narrator, and the joke that some people get but some people don’t is that dating in New York is a mess – it sucks. It’s not fun, complicated, and people treat others poorly, and you see this on the internet. The joke I’m trying to say is that “here’s this horrible story written like a fairytale,” and that’s the biggest joke of all is the fact that the movie even exists. 

Since so much of the film is based on the chemistry between the two leads, what was the collaboration process like with the actors?
My favorite part of filmmaking is collaboration, and that comes from both the crew and the cast. Every actor is directed and worked with differently; it’s just a different set of rules. Someone like Jaboukie Young-White is an improv genius, who you want to have multiple cameras on, and who you could shoot just a five-minute take of him riffing. Or someone like Francesca Reale calls me and says that her goal is to make Wendy this new complicated protagonist. She didn’t want people not to like her because she didn’t want a relationship. I loved that, so Francesca and I sat down for an entire day and went through every line of dialogue because she’s going to interpret this character. She said the words out loud, and we talked about every intention, and that was a very liberating and enjoyable hands-on experience in understanding that character together. 

Then there’s someone like Catherine Cohen who comes in, and it’s the Cat Cohen machine where you give her the line, and then she shows up on set, and it comes out even better than we wrote it. She adds these isms, and it’s like watching early Tina Fey do her thing. Someone like Brian Muller, who is a classically trained actor, has those exciting moments where you give the actor the lines, and you think it’s supposed to be one way, and then you hear them do it and go, “oh, that’s exactly how it’s supposed to be done.” That was exciting. Everyone comes in, takes the words, and does something exciting with them. There’s less improv than people think, but it was still a hyper-collaborative process, and since we live in the digital era, if we need to change the script, we can do that on set on Final Draft and get new sides, and then run with it. 

As someone who grew up in New York, was the film always going to be set there? 
I think it was always going to be set in New York. I spent seven years in L.A., and I think I was there because people told me that you have to live there as a filmmaker. I don’t feel that way anymore. I spent seven years pitching my heart out and never being told yes from any studio. Then I moved back to New York because I always wanted to live back here as an adult and when I came back – you know I just missed the bacon, egg, and cheese – I simultaneously got this movie financed and felt inspired. 

Also, there’s a reason that New York is the most popular place to film a movie, at least in terms of a rom-com. One, happenstance. Things can happen in New York that you don’t need to explain why it happened because the idea is that eight million people are bumping together – crazy things can happen all the time, and we accept that as the way it is. You can bump into an ex on the street 20 times in one day; that’s believable. You can also have magic. Things in New York are always talking to you, from the Subway signs to the mystic across the street and the cab driver. For an indie movie, it’s easy. You point the camera at whatever you want, and you have production value. 

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As a first-time feature filmmaker, is there advice you feel you’d give other young filmmakers starting? Or, comparatively, is there a piece of advice you wish you’d been given before you started? 
I’ll answer both. I think the best piece of advice I can give to other first-time directors is to trust your gut and know that everything is going to work out okay. Your movie is going to get made; it will happen. On a more practical note, pick a start date and tell people you’re making a movie. The second I started telling people I was making a movie on, say October 31st, and I know it sounds insane, but it manifested and became real, so tell people about it and pick a start date and stick to it. 

The piece of advice that I always wish I’d got was that one, everything is going to work out, and I think people did tell me that, but I didn’t understand it. And the more practical advice is not to have a ten-page, ten-minute scene that takes place in one location when you’re on a 15-day schedule in New York City. Figure out a way to condense it, so you have more time.