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'Dating & New York' Is A Rom-Com For The Swipe Right Era


"Dating & New York" is a rom-com for the age of swipe right for love. Milo and Wendy meet on a dating app. And because there are no particular sparks - or are there? - they draw up a contract - you might call it a never-nup (ph). It provides for benefits with no complications. But really, does it ever work out that way?


JABOUKIE YOUNG-WHITE: (As Milo) What if we were a movie? What would our movie be?

FRANCESCA REALE: (As Wendy) Oh, my God. We would be like a slasher horror film where Denzel Washington plays you, and Margot Robbie plays me.


REALE: (As Wendy) And we both get gutted and die together.

YOUNG-WHITE: (As Milo) ...And then we have to solve our own murders...

REALE: (As Wendy) ...And then we come alive in different universes and solve who murdered each of us...

YOUNG-WHITE: (As Milo) I like the different universes...

SIMON: Jaboukie Young-White, most familiar from "The Daily Show," and Francesca Reale, from "Stranger Things," are Milo and Wendy in Jonah Feingold's new film. The app-crossed lovers, or whatever they are, join us now. Thanks so very much for being with us both.

YOUNG-WHITE: Thanks for having us.

REALE: Thank you for having us.

SIMON: Jaboukie Young-White - Milo's pretty insufferable at first, isn't he? He insists he's perfect.

YOUNG-WHITE: Yeah. No, he thinks that he's flawless. There's nothing wrong with him. And then it becomes pretty apparent why he hasn't had romantic success thus far.

SIMON: Well, and Francesca Reale, Wendy kind of figures it out from the first, doesn't she?

REALE: Yes, she does. I think she knows exactly what she's signing up for, but she thinks he's the perfect pick for her little contract experiment with friends with benefits.

SIMON: Yeah, because he's kind of self-centered?

REALE: That, but I also think because she feels like anyone who's obsessed with love that much must be kind of like a safe bet.

SIMON: Oh, my. Well, what do they see in each other but don't want to say it aloud?

YOUNG-WHITE: Milo sees a future life partner but would never say that out loud.

SIMON: Yeah, yeah, because that would ruin their time together, right?

YOUNG-WHITE: Exactly. Exactly.

REALE: Yeah, I think Wendy sees an opportunity to just fully wear the pants out of this duo, but she would never say that out loud.

SIMON: Ooh. The moral center of the film, if I might put it this way, seems to occur in the ice cream shop - right? - where there is a true difference of opinion.


YOUNG-WHITE: (As Milo) Well, you just got to pick a flavor and then just go with that flavor.

REALE: (As Wendy) And why would I pick a flavor and just go with that flavor when I could try all the flavors?

YOUNG-WHITE: (As Milo) Because if you try all the flavors, then you never really get to experience just one good flavor at once.

SIMON: I wonder if I can get both of you to revisit that.

YOUNG-WHITE: I feel like it comes down to the core of what the two characters really - like, their whole M.O. and their mission statement for, like, what they want from relationships and when they - not so explicitly but explicitly lay that out. There's a lot of tension all over this bemones and caramel twists.

REALE: Yeah, I also think it, like, lays out, you know, kind of this millennial trend of passive aggression.

SIMON: Ooh, ooh. Go with that, if you wouldn't mind.


REALE: I feel like people can be very passive-aggressive. And this is, like, the first moment you see these characters really butting heads, like Jaboukie said, with what they actually really want. But instead of being direct - as direct as possible and clearly communicating that, there's this tension and anxiety. And the only way they feel they can safely share what they want is through this passive-aggressive way of talking about ice cream flavors. And, well, why don't you just want one? Well, I want several. I want to keep trying. Well, why can't you just have this one and this simple good one that you know is going to be good? And her - Wendy kind of clapping back and saying, like, no, I need to try all the flavors before I make that decision and just kind of this like round and round and round they keep going through in front of this poor girl, that poor sweet girl who did that scene with us. You're just, like, serving me sample after sample.

SIMON: You know, Jaboukie Young-White, I got to tell you, I am not fond of vanilla.

YOUNG-WHITE: Really? OK. See...

SIMON: But you made me a believer.

YOUNG-WHITE: Then you know what? I think maybe it really was that role that switched me because I ate so much vanilla that day, I was like, vanilla is actually really good. Like, I can't believe that I'd been sleeping on it that long. I was always a strawberry person. But honestly, like, I would say that if there was one thing that really changed my life from the shoot, it was, I like vanilla ice cream now.


SIMON: Oh, well, that - what a worthwhile venture then. I used to think that, you know, I didn't understand dating apps. I didn't understand meeting online, which I know has become quite common. But then I remembered when I was a reporter in India and an Indian friend saying to me, you know, the whole idea that you'll just walk into a bar or through the park and meet the person you're supposed to spend the rest of your life with, that's just insane - how can you Americans do it? Now, my friend was making the argument for arranged marriages. But I wonder if the algorithms are making a case for finding each other but with a little guidance these days, if that's what your friends are doing.

YOUNG-WHITE: Hmm. I definitely think that there is like a - maybe not invisible but like a silicon hand that is moving us toward certain people or, like, towards certain things - not even just on the apps alone, but, like, for example, if you go to someone's Instagram Explore page, you'll pretty quickly get a sense of what their type is. Like it - if Instagram is like, we think that you think this kind of person is hot. So we're just going to show you this kind of person over and over and over again. I feel like that has to affect what you are looking for in a partner at a certain point - like, if you're seeing all these, like, algorithm-chosen people who are supposed to be, like, the best version of this thing - there is, like, sort of a digital form of fate now - almost.

REALE: A hundred percent I would agree with that. I think there's definitely, you know, a - there's an algorithm in - I think in every aspect of our lives now that's kind of gearing us in a direction and telling us, you know, what we should like and what we should eat and recommending, like, food and movies and people to us - I think it's just, like, so ingrained in our - in the way we live our lives now that it's kind of - it is really interesting. It's also kind of scary.

SIMON: Yeah, yeah. Francesca Reale, Jaboukie Young-White - their new film, "Dating & New York" - out September 10. Thanks so much for being with us.

YOUNG-WHITE: Thanks for having us. This was fun.

REALE: Thank you for having us. Transcript provided by NPR, Copyright NPR.