‘Dating & New York’ Writer-Director Jonah Feingold on Filmmaking and Modern Love

Once Upon A Time In New York City… Two heartbroken millennials, cursed by the paradox of choice, can’t escape their romantic pasts and presents as they attempt to find love in the city that doesn’t sleep – but sleeps around a lot.

Dating & New York is snappy, intelligent, aesthetically pleasing to look at, and it doesn't make those out of touch with dating apps feel...too old. What feels like a modern retelling of When Harry Met Sally, Jonah Feingold leans fully into the rom-com structure, sprinkled in with his keen directing eye and his finger on the pulse of NYC twenty-somethings. 

I had a great conversation with Jonah about his new film, the impetus for this story, his filmmaking journey, and our shared love of the movie Hook. Plus, Jonah shares invaluable advice about filmmaking that first-time filmmakers should absolutely take note of!

This interview has been edited for content and clarity.

Sadie Dean: There's just something so magical about New York City, from the trees, to the taxis, to the people and everything in-between and I love how you made the city a character within the film. It also feels like a modern retelling of When Harry Met Sally, which I'm also a very big fan of, but now with dating apps. What initially inspired you to tell this story?

Jonah Feingold: Well, first off, thank you for watching the movie. And thank you for the love on the film. The original impetus for the story was very much what I think you're highlighting, which is that I love Nora Ephron's movies, I love romantic comedies. And I felt as if there really hadn't been a rom-com that explored the minutiae of modern dating and the technology of it in a way that is the way I hear my friends speaking about it. Text message sequences, Instagram stalking, talking about who belongs on the grid versus a story post, you know, these things that are certainly too micro for a studio movie, I could see an exec giving the note that this is too topical, you know, it's going to become irrelevant, we can't have a scene about an Instagram grid. But that's the beauty of indie movies. I actually think it's such an important thing in modern romance that is deserving of its own scene. And that was the main impetus for that.

The other main impetus was being able to make a movie and having spent seven years in LA trying to get a script off the ground that was a larger film and pitching on stuff and just gigging around and trying to make that infamous first feature film, it was like, alright, I need to figure out what we can go make and being a New Yorker movie that takes place around the streets in New York and bars and restaurants. And that was a starting point. It was kind of a combination of all these things of let's put a script together that's going to be shootable and also going to be unique in the canon of romantic comedies.

Sadie: How many shoot days did you have on this?

Jonah: Fifteen.

Sadie: Wow, that’s a short turnaround for a movie like this. How many pages were you shooting a day with it being so dialogue heavy?

Jonah: We had one day where the diner sequence, which is like a fun film school lesson that I should have picked up on, you don't need to spend 10 pages on one scene in one location for an indie movie. And this is good, because this is script related, but if you have one scene that's 10 pages in a diner and you're an indie movie, only if you're an indie movie, that is not a good use of your production time. I think that scene ended up being about two minutes long. But because most scenes are two or three minutes long in every movie, but little did I know when I was going out to make it, that that there were 10 pages of really great dialogue but all you needed for the story was the two-minute version of it. And yeah, I agree with you,15 days for an indie film I think is common enough if you're like a single house location or a cabin or something but a 22 location kind of commercial rom-com in 15 days I would not recommend it if possible to avoid [laughs] but I think nonetheless speaks to the amazing crew that we had, and the amazing cast that we had, and just everyone's shared unique vision for what we were doing. And it was a dream come true.

Sadie: I read that you're also a co-host for a dating relationship podcast. Were you doing that in tandem with this film? Or was this before you started writing? Or was it kind of hand in hand?

Jonah: Yeah, I used to host a podcast for Hinge. It happened after we were done shooting, we were in post-production. And I have a dear friend who worked for Hinge at the time and they had recruited her and me to start a podcast together. And so, we were editing the movie, and I was hosting this podcast. And you know, there's certainly a part of me that was like, great, a lot of new information that I could have put in the movie. But we were able to take some of that information and put it into our post-production process. And it just helped sort of solidify the need for this film. There was a lot of stuff that I was just like, great, our movies really gonna do well with this audience. And I was able to sort of get an audience excited about it early on when the movie comes out September 10. I will certainly be falling back to that audience and saying, “Hey, remember that movie I mentioned I was working on two years ago, like it's finally out, and you should go see it.” [laughs]

Sadie: [laughs] Swipe right if you like it.

Jonah: Please swipe right, yeah. [laughs]

Sadie: When you're writing an ensemble piece like this that is so dialogue rich and heavy and I love how the dialogue is very rhythmic and playful, how are you approaching your character development, knowing that you're going to have such heavy dialogue pieces with them?

Jonah: Yeah, that's a great question. For the movie, the structure was pretty set, I wanted it to be very simple, you know, they meet, they break up, they get back together. That's why I love rom coms. Because within that, you can then start to stretch out and figure out what you're going to do. And then I love writing dialogue. I don't know if I love writing treatments, and outlines and perhaps for better or worse, but I think it's really fun to come up with clever lines. You can hear something on the street, or you're just on the subway or in a cabin. I have a whole Notes app, that's basically just like versions of one-liners or conversations that are supposed to be hypermodern relatable, but also have an element of this will come back to this character in the butt in an act one or two, or there's something deeper here that's supposed to have meaning.

For the two characters, it was supposed to be very rhythmic. When I read it out loud in my room, when I'm writing, I'm sort of like ta-da-da-ta there is a tempo to it. And that begins even early on in conversations, my composer where I'm just working on the script, and I'm like, Grant, can you send me something to write to? Whether that's him making a playlist or creating some original music, but the characters will ultimately serve as their theme. So, music, whether you hear it or not, is a huge part of the writing process.

Then in terms of character development, it's pretty much like, what does this character want? And then what is their flaw? And how do they change? And these are all things that have been ingrained in us screenwriters. But I am actually hyper dyslexic, I could barely read until I was in third grade. I was always ridiculed; I was put in special reading groups for my lack of ability there. For me, it's always been what's the simplest, simplest way I can express this. Milo wants to cuddle. And that says it all. Wendy doesn't want to be an ex ever again. Simple things that can help drive the characters and whatnot forward. I also wanted to avoid plot at all costs. [laughs] I wanted to make sure in a sense of like, I didn't want it to feel like a rom-com where the plot was driving the narrative. I wanted it to feel like these characters were sort of just living their life and then the thing that was sort of helped drive the narrative was the fairy tale approach to the film. And that's sort of the way it came out the other end and I will say, just to your point about dialogue and rhythm, a lot of that is the editor as well. Hanna Park, our wonderful editor, she would spend tons of time pacing it out so that it felt like this fun, engaging conversation.

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Sadie: That's awesome. Yeah, working with an editor is a whole other tool, or at least way of how to communicate story as well. And I think a lot of a lot of people don't respect that editing process as much as they should, especially with something like this.

Jonah: Oh my gosh, Hanna and I spent the longest with the film. If you look at who spends the most with it, I guess my producer Joaquin as well, but you know, you kind of have these little relationships with people as you're making the movie and then the editor Hanna and I spent months on this movie together. I'm sure when an editor reads a script, they're thinking, “Cool, you know, 50% is isn't going to make into the cut.” [laughs] But we don't know what that is until you see it sort of. There’s a ton of value in onboarding your editor early and having those early conversations. I sent her the script, and I said, “What are your notes on the script?” And I did that for my next film. And so, you're absolutely right, the editor is ultimately still going to make your dialogue real and sound right and that affects the way that the characters listen to each other.

Sadie: I'm also curious with your casting process, once you casted your main characters, did you do a table read and then do any rewrites on the spot? A lot of it felt like it could have been improvised and I wonder if that was just all because of your writing or was it just letting them have at it?

Jonah: Great question. In terms of a table read, we never had a table read, at least with the actors that are in the movie. We had one day where Francesca, very wisely, was like, let's go through the script line by line and let's just talk about it. And I was like, I love that, especially Wendy's character, I'm not a 25-year-old woman who lives in New York, I'm writing what I believe this character would say, but it was amazing to have someone as collaborative as Francesca who could say, “I don't know if I would say this this way. I think it would be more sincere to do it this way.” And I was like, wonderful. And then she would do it. And it's like, great, I totally see it. And that was a really beautiful part of the process was having that sort of level of collaboration. And of course, inviting all the department heads to weigh in on scenes and dialogue, because when you can start to work like that, everything just gets better. When your production designer has the freedom to say, you know, it'd be cool in this scene, the prop is this couch in the middle of the street, and that's something that the characters scared to do, and I'm like, brilliant, yes, it's like the Pixar method. You have everyone contributing to layer the scenes. That was something I took a huge advantage of, whenever I could use their time to help make the thing better.

In terms of improv, there's actually a shockingly low amount of improv. I think that I definitely invited the characters and the actors to do improv, some were more receptive than others. I think of one particular scene where a brilliant comedy actor who didn't want to do improv, and I was like, but you're you. And they were like, “no, you're gonna want to book” and I'm like, “OK, I guess I want it to book.” What I think is valuable is that you do improv and then you also take what you want from the improv. And then you redo it. Some actors, you want to just make sure that they're doing it to book because they're so much better at doing it to book. And then people like Cat Cohen, you give her the middle, and she will start you and end you and like take you into it, and she's obviously got such a unique way of delivering lines that you want to let her do her thing. And then what I will say, though, is that on a practical standpoint, because we're an indie movie, we only had one camera, if you're going to have an improv heavy actor, heavy hitter comedy person come in, tell your line producer and camera department to get you a second camera, so that you can have two cameras going at once, so you don't miss any of that sort of crossover with the scene partner. And you have two angles at once, they won’t have to recreate it.

Sadie: Great advice on having the extra camera, especially when you have that heavy hitter player on board. Tell us about your filmmaking journey. I know you came out to LA, did film school out here went back to New York, you have a love for rom-coms, and Nora Ephron - was there a specific movie or maybe dialogue or character that gave you that jolt of, that's what I'm going to do, I'm coming to LA and I'm going to do this.

Jonah: Yes. [laughs] For me, it was the movie called Hook. And that was when I was very, very young, I saw that film. And I was like, OK, directing is the path. think I was lucky enough to be one of the people that knew since they were big enough to hold a camera that filmmaking was what I wanted to do. But that's still a very difficult thing to break into, and still is, and coming to LA to get into film school was just like, I was really bad at everything else, got really bad grades, didn't know how to read, all these different things, and film school was like a visual medium. And I had been making movies since before even YouTube existed, and it was just the dream to go to film school. And to think about that, at least in the same way that was from a production standpoint where like back when, you just couldn't own a camera because they were too expensive, so you went to film school. But the movies that made me want to move to LA was like the idea of this sort of Hollywood studio system I've very outwardly confessed that I want to make movies like, You've Got Mail all the way over to like Night at the Museum and Jumanji and Men in Black. I want to make feel good studio family movies. And I also want to make rom coms and those movies get made in the studio system and in Hollywood. And it was a very attractive thing to just be like, ‘wow, I get to go there and live out this dream of LA and Hollywood.’ Of course, the ironic thing being that I didn't really get to make a movie until I moved back to New York. But everyone's journey is different.

We all have that script we've been working on for like seven years. And my script, I've had that one for a while, it's called Wendy, it's a rom-com about Wendy from Peter Pan. And it's got swordfights and it's in New York and it's modern, and I love it. But we spent so many years trying to get this thing made and different ups and downs and notes and all this different stuff, and I was like, ‘how does anyone just actually make a movie?’ And once that clicked, like indie filmmaking is simply just your budget, your actors, and a camera, then things started to click in terms of OK, this is how we can make this dream happen.

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Sadie: I’m also a very huge fan of Hook. I remember when it came out, I had a little Rufio water toy. Practically always had it with me.

Jonah: No way!

Sadie: Yeah, and in grad school, I wanted to make my thesis on the Lost Boys, but I never did it. Last question, advice to multi-hyphenates like yourself, who are going to approach making their first feature film that is dialogue rich like yours, what is something they should be aware of or maybe something that you learned on the job?

Jonah: That cliche advice, but stick to your gut. Always look back at that first deck you made or that draft that you went off with, because your original instinct is always there to help you. Whether that again, it's your Notes app, or it's your deck. Like, I looked back at my production deck way after the movie was done, and I was like, ‘wait, why did I not look back at this?’ There's so much I could have just used that was really helpful.

I would also say that getting to that position, you have your script, you're the writer, director, producer, multi-hyphenate, don't be afraid to change things that will help make your movie better. And don't be afraid to have an understanding of production like an indie movie, there's just things you can do once you start working with your line producer, there are things you can do in the script that really won't affect the story, but that will make your life as a director so much easier because you are not cheating. Maybe you have 35 characters with speaking roles, and you realize that 10 of them are really just lines that should actually go to your other characters, well, then your budget goes down. And it makes it easier to do a couple of other things.

And I think one of the things you can do is, one, pick a start date for your movie that you're going to make, no matter what budget you have, and say, you're going to go make a movie. You’re telling everyone that you're gonna go make a movie, you're at dinner with friends, you're out on a date, you're in a taxi, people ask, “What are you doing?” “I'm making a movie.” Then they're going to ask you about it. And that forces you to talk about it. And when you talk about your movie, things start to fall into place. The amount of times that I've come up with major story beat fixes, by simply just talking out loud and realizing, ‘wait a sec, I just said it so much simpler.’ Then once you're on set, because you've now established your start date, you're going to make a movie, be collaborative, be kind, create a cool and fun environment for everyone, because ultimately, they're all doing you a favor, which is making an indie movie, and be nice and respect people's time. And you want to just be morally correct and you want to be a good person. And then if they trust you and see your vision, then you're going to have a great experience and a great outcome. And I think it's all about having a shared vision. And if they see your vision, everything will fall into place, also get a great DP who you love and hire Maria, who's the best DP in the world. [laughs]

I still write directors all the time, I'm like, “Do you have 15 minutes for a phone call?” I just got to speak to a director named Marc Lawrence, who directed Music and Lyrics and Two Weeks Notice, and I was like, “What's the key to great rom coms?” Because he's made so many. And he was like, “Well, I don't know. You tell me.” I'm like, “What do you mean, man, you tell me!” And he mentioned, a great script and great chemistry. And in retrospect, I 100% see what he means looking back at his movies, especially because going in with an undeniable script, that's bulletproof, from people you trust is the best thing you can possibly do. But you must finish it. Because I know a lot of us can spend many years working on our script, and it needs to get made. So, at some point, you gotta just go do it.

Sadie: You're preaching to the choir here, Jonah! I think that's wonderful advice, along with everything else. Well, thanks so much for your time. Thanks for your movie. I hope there's something next in the pipeline for you that you're doing that we can all see the big screen.

Jonah: Aw, Sadie, thank you. Appreciate your time. 

Dating & New York opens in theaters and VOD on September 10.