Once Upon a Time in New York City… thus begins the creative and quirky romantic comedy, Dating & New York. Narrated by doorman Cole, (Jerry Ferrara, who I knew as Entourage’s Turtle), we are plunged into the waters of the modern dating world via the latest app, MeetCute. Curly-haired cutie Milo (Jaboukie Young-White), who thinks of himself as a “between relationships dulah”, matches with sarcastic millennial Wendy (Francesca Reale), a girl afraid of commitment and real human connection.
Two dates later, and the duo struggle to define their relationship. “You’re playing chess, we’re playing Xbox,” Milo muses about women not understanding men. He is shocked when Wendy doesn’t understand his reference to blowing on an N64 cartridge. Wendy introduces a contract that will hopefully be beneficial to both parties: “Best Friends With Benefits.” Milo manages to negotiate with Wendy until she adds “cuddling” to the list, but one thing is strictly off limits: neither can say “I love you” in an emotional context.
The playful dialogue, especially between Milo and Wendy, is fast-paced and witty. The style is very Woody Allen with a sprinkling of Disney magic, and there is an emphasis on emotions and thoughts over simplistic over-sexualization. Random asides are relatable in a way I wasn’t expecting. At one point, Wendy tells Milo that he is like an episode of The Office that you know line by line—“you just know what to expect.” Another where she plays with his hair (“your curls are literally perfect today!”) finds him insisting that “every curl has a story.”
Their relationship is so cute, and both performances sizzle with chemistry and honesty. I would watch an entire series with Milo and Wendy just having conversations. Their friends Hank (Brian Muller) and Jessie (Catherine Cohen) also get a decent amount of screentime with a budding relationship of their own, including a hilarious impossible hunt for an affordable NYC apartment.
An element of fantasy and whimsy keeps Dating & New York light and fluffy at all times. Writer/director Jonah Feingold makes the most trivial concepts into romantic imagery, including a beautiful kiss amongst piles of garbage. On a purely technical level, I had such a great time watching. It is not an easy feat to display phone screens or emotion while texting. One moment with an emotional breakdown, conveyed through shaky text and zoom-in, completely envelops the audience in the headspace of the character.
Watercolor renderings give an almost magical quality. Dating & New York is clearly a love letter to New York in its full messy glory. Some of these jokes will only land if you are fluent in New York culture, and each spoke to me on a personal level. Though I haven’t been on the dating scene in a very long time, navigating the technologically complex waters seems just as puzzling as the dating websites of the late 2000s. This is one of my favorite romantic comedies I have seen in a very long time. A friendly reminder for all the single folks out there: “you’re 80% more likely to get swiped right if you use the word ‘guacamole’ in your profile.”
Dating & New York screened at the Tribeca Film Festival via Tribeca at Home on Sunday, June 13th.