Dating & New York, perhaps the first true romantic comedy of the roaring ’20s, very much wants to be the When Harry Met Sally for the Tiktok generation. It nearly gets there, too. Time and again, writer/director Jonah Feingold pays very clear homage to what might just be the best romcom of all time, often cribbing entire scenes from the Nora Ephron-written masterpiece and reimagining them for this millennium. If it weren’t done with such clear affection and appreciation, it would be annoying. But Feingold, here making his writing and directing debut, clearly knows from whence he came and he’s not afraid to pay his respects. That coupled with a central couple so charming they’re endlessly watchable make the film something quite modern, enjoyable and sweet, if not always profound or terribly deep.
The Harry and Sally of Dating & New York are Milo (Jaboukie Young-White, the upcoming C’Mon C’Mon) and Wendy (Francesca Reale, “Stranger Things”), two Gen Zers who meet on a dating app (it’s called “Meet Cute”), each clear about what they’re looking for but neither quite finding it in the other. Milo is a romantic at heart; he’s ready to fall in love and get off the apps forever. Wendy is less interested in anything serious, but she’s eager to have a reliable partner who’s available for regular sex and all the enjoyable things that come with having a partner: a date to weddings, someone to go to the movies with, you get the idea. A la When Harry Met Sally, there are the best friends, too; here, it’s Jessie (Catherine Cohen) and Hank (Brian Muller) who are besties with Wendy and Milo, respectively (and yes, they fall in love…). Together, the four of them navigate current-day New York City as young professionals trying to figure out just what kind of life they’d like for themselves. Among the four of them, but especially between Milo and Wendy, there’s a brisk witty banter that keeps the film moving at an energetic pace. And finally, rather than intersperse the proceedings with love stories from exceedingly adorable couples, Dating & New York instead employs the use of a charming narrator (who this turns out to be is obvious early, but also a bit of a spoiler, so…), a New Yorker who keeps us up to speed on the comings and goings of these lovebirds.
Though Milo and Wendy don’t hit it off after their first date, they are compatible enough that Wendy proposes something that really only flies in the movies: a “friends with benefits” contract, one where both get the dependability and affection they’re looking for without the all the pressure of a grown-up relationship. Both are still able to date other people and each of them has to abide by several caveats in the contract (they cover everything from snuggling to sleepovers). Though Feingold’s script is smart and fresh, it’s not exactly original. And in fact, it’s often downright predictable. Why yes, Milo does “catch feelings” for Wendy, in a way that is both endearing and pathetic. He tries to kiss her outside a restaurant, a sweet gesture that shouldn’t be a big deal for a couple as enmeshed in each other’s lives as they are. But she rebuffs him, intent on keeping to the terms of their contract, eliciting something like a wounded puppy look from Milo. These two are on such different pages with their relationship, if it weren’t a movie one would wonder what they’re doing together in the first place.
Dating & New York deserves quite a bit of credit for much of what it gets right, from the spot-on send-up of dating in the 21st century to the way it pays its respects to all the romcoms that’ve come before it. Will Feingold’s efforts go down as a classic in the genre? It’s not impossible, but it’s also not likely. The films this one pays homage to have a sense of timelessness, a universality to their narratives. Given that it’s a film so set in the moment in which it takes place, there may come a moment in the not too distant future where Dating & New York feels, well…dated.
Dating & New York is now streaming wherever you rent films.
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