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

With its signature liveliness, unapologetic attitude, and visual splendor, New York City has so long been a set of romantic comedies that this location has become a cliché. So, how does Jonah Feingold, the writer/director of “Dating & New York,” aim to make his mark on this sparkling skyline? By creating a postmodern rom-com that blatantly snatches from iconic influences to deliver an irreverent commentary on the genre and modern romance.

Jaboukie Young-White and Francesca Reale star as Milo and Wendy, a young couple who hook up, ghost each other, then circle back to become friends with benefits. Could this be the winding path to true love? Unfortunately, their respective besties—a preppy Brian Muller and a sassy Catherine Cohen—don’t think so because someone will always “catch feelings” and wind up heartbroken.

“Dating & New York” plays like “When Harry Met Sally” for twenty-something Millennials. The classic rom-com’s thesis that men and women can never truly be just friends is updated to f*ck buddies will always lead to heartbreak. And just as the titular ‘80s lovers ignored all romantic advice, Milo and Wendy dive into a relationship of friendship, sex, and cuddling—but no romance and no “I love you”s. Perhaps in a nod to Billy Crystal, Milo is a stand-up comedian. Likely in a nod to Meg Ryan’s Sally, Wendy is a charming, controlling, and has an intense affection for turtlenecks. She reasons this friends with benefits plan is fine because it’s all laid out in their contract. (Clearly, she’s not seen “Can’t Buy Me Love” or “To All The Boys I’ve Loved Before!”) Of course, Milo falls for the girl who swears she’ll never love him and suffers when she goes on dates with other guys. Lucky for him, all these men are not threats as much as a parade of flimsy fuckboi stereotypes: douchey fedora-wearer, arrogant app-developer, and whiny podcaster who interrogates his exes about what went wrong.

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. When he can’t score a location, this inventive director uses a whimsical watercolor painting as an establishing exterior. An opening credits sequence full of these artworks helps paint the expectation of a romanticized version of New York City, which is supported by an aggressively saccharine score. Strings, piano, and choral singing suggest this will be a fairy tale, while the jaunty narrator (Jerry Ferrara) sets up a snarky twist with declarations like, “[New York] is the city that never sleeps, but sleeps around.”

These flourishes collide with a high-saturated color palette that seems a nod to Wes Anderson’s aesthetic, with its warm autumn golds and blushing pinks. However, the settings are decidedly less twee; towering piles of garbage bags frame a first kiss. Meanwhile, Feingold’s characters are more earnest and openly neurotic, perhaps reflecting the online dating vibe, where kinks and dealbreakers are in bio blurbs. Speaking of which, in a knowing nod to rom-com convention, Milo and Wendy are introduced through a dating app called “Meet Cute.” It’s good for a laugh but sadly undermines what should be a pivotal moment in establishing chemistry. Thankfully, Young-White and Reale recover with a winsome first date scene, where they definitely share a spark. However, this romance doesn’t develop into something hot. They’re cute but not clicking.

Instead, the subplot about the sidekick besties falling into a whirlwind romance (another “When Harry Met Sally” element) steals focus. Perhaps because Muller and Cohen do click, but more likely be Catherine Cohen is absolutely mesmerizing. From her first crooked smile and snapped witticism, she proves the Carrie Fisher, funny, radiant, and—why isn’t this movie all about her?

Dazzling scene-stealer aside, the problem is Feingold stitches together comedic bits instead of a flowing narrative. For Milo, there’s a flashback to a past relationship blow-up and an achingly awkward subway break-up (with a standout cameo from viral comedienne Eva Victor). For Wendy, things abruptly spin into the fantastical, with one bad date becoming a sidewalk therapy session—complete with curbed couch and working lamp—and another turning into a literal press conference, where she’s badgered about what she’s looking for. Some of these are imaginative and fun, but they create a chaotic pacing that makes the stumbling romance plotline woefully episodic.

“Dating & New York”s meta-commentary on rom-coms is initially intriguing, from the Meet-Cute app to Milo lamenting he’s a “manic pixie dream boy.” However, Feingold never strings together a cohesive criticism or narrative, leaving the film to feel more like a brainstorming session or a work in progress or even a snarky Twitter thread. The story runs out of steam before this clunky coupling even hits brunch (because, of course, there’s a brunch scene). So, we’re left waiting impatiently for the happy ending. But be warned, Feingold thinks he’s too smart for that. True to the cynicism that takes superficial swings at rom-coms throughout, he delivers a final beat that is so outrageously misplaced that I rewound twice to make sure I wasn’t missing something. I wasn’t. It was just that bad. [C-]

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