Ask a Rom-Com Expert: Tribeca Q&A with ‘Dating and New York’s’ Jonah Feingold

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Selome Hailu talks to Dating and New York writer-director Jonah Feingold, who dives deep into the rom-coms he loves, the ones he hopes to see and create one day, and the brief moment when Letterboxd made it into his script.

“I got a note that that was too niche of a reference. I will never listen to that note again.”

Spielberg movie that, famously, he doesn’t acknowledge liking. Although in recent years, he has come out more publicly and [recognized that] there's a whole generation of ‘90s babies who love this movie more than life,” Feingold rattles off, as if this is a speech he’s given many times before. 

And he’s got a lot to say when it comes to his love of romantic comedy. He’s quick to shout out Nora Ephron, as any rom-com-maker must, and also finds himself drawn to weirdness and whimsy wherever he can find it. “It’s a comedy, but it’s got an Enya song!” he says, explaining how L.A. Story influenced his career. “And a rain montage. And it’s got magical billboard signs!”

Feingold’s debut feature, Aneesh Chaganty. “USC Mafia is real,” he says—this explains why Chaganty makes a tiny cameo in the film’s opening montage. “[He was] my first friend on day one of film school. And he was the first director to skyrocket out of USC in our year.” 

Feingold hasn’t publicly revealed all of his influences, though. “This is one that’s not on that list, but when I was editing the movie with Grant Fonda had finished creating the original score. 

Feingold has spent his life watching a lot of rom-coms, everything from the classics to Netflix originals. He also spends a lot of his time dreaming up new ones: he’s currently working through how he might pull off a “dog rom-com,” and describes the next film he wants to make as “Chef meets You’ve Got Mail,” following a cook, and the food critic who gives him a harsh review because he took over the restaurant space her mother lost to the pandemic. 

Soon after Dating and New York’s virtual Tribeca premiere, we picked Feingold’s brain about everything the genre is capable of. 

Let’s get into our rom-com speed round. Starting with the basics, what is your favorite New York rom-com?

When Harry Met Sally.

What’s a non-New York city that needs more rom-coms?

Okay. Okay, hold on. I’m gonna get this. My head is like, ‘Disneyland? Does Orlando, Florida need a rom-com?’ But I don’t know if I like that answer. Does Montauk count? That’s still in New York, but it’s not the city…

You know, here’s my answer: Let’s go with Palm Desert, California. My grandparents lived out there. It’s a bunch of old people living in a version of a retirement city, and they’re all dating each other. They’re all trying to rekindle love and romance, so I think it is a very romantic place. And that sort of desert landscape, we really haven’t seen it in a rom-com sense. So Palm Desert is my answer. Some 80-year-old people playing golf together and falling in love on the golf course, having already lived such a big life. It’s getting into Nancy Meyers territory perhaps, but I think that could be a fun visual place.

Who is your favorite romantic duo? Who’s got the best chemistry?

Oh, boy. Of all time? My vote is Glen Powell in Set it Up. But it’s Tom Hanks and Meg Ryan for me. But now I’m actually curious, can you answer that question? Who has the best romantic chemistry?

Oh, you’re not supposed to be interviewing me...  

I’m just curious. I need to know your answer to this.

Well, I’m a huge Lonely Island girl, so recently I just loved Cristin Milioti in Palm Springs.

They were amazing.

Of all time, though... I did say romance and not necessarily rom-com, so I’m going to go with Jacques Demy. Have you seen it?

Of course. Amazing movie.

Nino Castelnuovo. They just have such insane chemistry… I’ve got a bit of an essay on Letterboxd about how that movie made me feel.

I’ll be reading that.

To expand on that, what’s a duo of actors who haven’t done rom-coms but should? Your rom-com OTP?

I don’t think we can call Anthony Ramos to do a rom-com. I was having a conversation with my friend where we’re like, “If you were his agent, what would you advise him to do?” And my biased answer was that he’s so charming and talented and New York, I would just love to see him in a romantic comedy.

Also, Ziwe [Fumudoh] is a friend, and I’m trying to get her to possibly do a rom-com, too. I just love her energy, and I feel so lucky to have met her quite before she blew up. And therefore, now she has my phone number, so you know, maybe she’ll take my texts.

The dream is to take people who want to come to play in the rom-com genre—and I say that in a sense of the way that Marvel might come to actors and say, “Hey, do you want to come wear a cape?” But in this case, ”Do you want to come jump into romantic comedy? Hijinks will ensue. It’s gonna be feel-good. It’s gonna be cheesy, but it’s gonna be fun.” 

What’s the best or most creative meet-cute you’ve seen in a movie?

A movie called Michelle Pfeiffer, and they’re both parents. They have to take their kids on a field trip in New York, both are single parents, and their kids miss the field trip bus. So then they’re basically glued together throughout the entire day around New York City, trying to get their kids on the field trip. Of course, everything goes wrong. He’s a reporter, she's working in politics, the whole thing blows up. 

I just really loved this idea that it’s a meet-cute that sets you up for a ticking clock: it all has to happen in one day. I love movies like that where you’re just locked in for the actual time that it exists. It’s an older movie, very creative in of the way that the set-up was initiated.

What’s your dream meet-cute, one you’d love to direct?

I got it. I got it. This is perfect. I actually just thought of this the other night. Here's my idea: it’s called Crossing Paws. I secretly really want to direct a dog-rom-com. Something to the effect of this movie with Uma Thurman, The Truth about Cats and Dogs. Great rom-com. Weird, but it’s great.

Here’s my dream meet-cute for a movie: basically, everyday in Central Park, Bethesda Fountain, between the hours of 5 a.m. and maybe 10 a.m., dogs can roam off-leash. I was there scouting for a project, and there were all these dogs running around. It was magical. My sister and I turned a corner and a Golden Retriever ran past us like a mystical unicorn. Everyone’s out there, New York adults, they got their AirPods in, some are more attentive to their animals, some are not. 

So basically, we hone in on a workaholic and someone who is very carefree, and the dogs that they have are representative of that. One dog knows all the tricks, very obedient, and the other dog is kind of scrappy and just runs around. Only the thing is, these are same-looking dogs. They start grabbing each other and get into a play session, one owner thinks it’s play, the other one thinks it’s aggressive. They bump into each other and start negging each other. But! The dogs switch! So when they go back home, “Wait, my obedient dog here doesn’t know ‘sit’ anymore!” And, “This is weird, how does he know how to get the cookies?” 

Basically a meet-cute wherein two owners of the same type of dog accidentally switch. It’s kind of like The Parent Trap meets New York-set rom-com. Crossing Paws. You heard it here first.

We’ll be looking out for it. Next: what is the best rom-com trope? 

I love the midpoint beat in rom-coms where both characters get what they want, just not how they expected it. I don’t know if it’s so much a trope, but it’s something that we really explored in Dating and New York. Let’s call it the metaphorical g of the contract. You’re both on board. You're gonna help each other get the promotion. You’re going to help write the article. It’s the I’m-cool-using-you-to-get-the-article-done, something to that effect. 

But that’s my filmmaker [answer.] My fun one is any sort of basketball scene. We don’t have one of those, but I love it. Two characters, shooting the shit, playing basketball, when you know those two actors have never played basketball once in their life.

Are there any major rom-com tropes you don’t like? Something that the genre should do away with or revamp and fix?

I think that the way we explore ing characters should be fixed. I think that it’d be great to have ing characters feel less ing. The “funny best friend” for both of the main protagonists is always a tough one, because you want them to really stand their own ground. I felt so lucky to have Brian [Muller]. Cat’s performance is exceptional. I think she’s such a star. I think the idea of ing best friends… let’s lose the word ing, and figure out how those characters are integral in the love story.

Also, the way we end rom-coms. I would love to start figuring out ways to subvert the endings. I would love to figure out how we’re really surprising an audience. Because it’s either get together or they don’t. But what’s in between that? I don't know what it is. I feel like La La Land kind of did an interesting thing [with its ending]. And obviously Palm Springs, which is a rom-com in so many ways.

What’s a movie that wasn’t a rom-com but should have been? Any characters who had all the chemistry but just needed to lean in?

Here’s a hot take answer. I feel like Gal [Gadot] were trying to figure out their romance amidst the world ending. You know how some of these superhero movies are genre-first? Like, you could argue Guardians of the Galaxy is just an ensemble comedy set to the backdrop of an invasion. And Wonder Woman 2 could have been a great rom-com, I think. 

Is there a director who hasn’t done rom-coms, who you think should? Who’s got the chops?

I’m gonna shout out my friend Gore Verbinski, director of the Pirates of the Caribbean movies. I think he romanticized those. He can make a great, epic romance with the way that he crafts films. 

That concludes our rom-com quiz. But I know you’re an avid Letterboxd member, so before I let you go, would you tell us a bit about how you use the platform?

I love Letterboxd. I now have a new relationship with Letterboxd as someone who has a film on there. Like, do you read the low reviews? Or do you only read the positive? Everyone’s entitled to their opinion, and I think it’s fascinating to see the way people interpret stuff. Sometimes even the lower reviews are still technically what we were doing. What they’re saying is accurate, but it’s a matter of taste.

I love that you don’t necessarily have to make a review; you can do more of a comment, you can make notes to yourself. I will log films that have great use of location. “Okay Jonah, come back to this movie because it makes excellent use of diners in New York.” I would have never discovered a bunch of movies from the ‘90s and ‘80s, [like] Crossing Delancey. A movie I would have never discovered had it not been for seeing my friend on Letterboxd watch it, and I was like, “What’s this?” I just love being able to log—even during this interview—I love being able to keep track of what I’m watching in a super clean way. 

I really want to write a Letterboxd love story, which would basically be You’ve Got Mail, but they meet over Letterboxd and have conflicting tastes in movies. To get the rights to talk about any of the movies is going to be difficult, but maybe as a fan-fiction, YouTube thing. We could probably pull something off. Someone sent me [the story about the couple who met on Letterboxd] and said, “This is up your alley.” I was like, “Letterboxd lovers! Of course!” I think it’s very real, by the way, sort of in the way that Spotify playlists were once a thing where you could follow someone and fall for their taste. Now, it’s in the indie film scene, [falling for] their Letterboxd. I think there’s a lot of potential there.

I had you guys in a cut of our movie in 2019. We were doing Eva Victor’s intro. Originally, it was that [she had met Jaboukie’s character] on Letterboxd. But I got a note that that was too niche of a reference. I will never listen to that note again.

’Dating and New York‘ has been picked up by IFC Films for release theatrically, on digital platforms, and Cable VOD in September 2021.