Written by: Robin C. Farrell | September 9th, 2021
Dating & New York (Jonah Feingold, 2021) 3 out of 4 stars.
Through a storm of dating apps, Wendy (Francesca Reale, Yes, God, Yes) and Milo (Jaboukie Young-White, Vanilla) make a match. Both are courtship-weary millennials still pining for romance and, despite a fantastic first date, they ghost each other. They’re reunited, however, when their best friends meet and start dating. Wendy, a pragmatist, concocts an idea (and a contract): best friends with benefits. Milo, an idealist, is dubious of the arrangement at first, hoping for a real connection. Still, despite warnings from friends and Milo’s own misgivings, they proceed into the good, bad, and confusing.
This is, undeniably, influenced by beloved romantic comedies of the ‘80s and even ‘90s (especially When Harry Met Sally), presented as a fairy tale within a charming but largely unnecessary framing device. Despite the title, Dating & New York doesn’t really focus on its geography all that much. It could have been set in any number of places, but not in any time. From the jump, this is an of-the-moment story about dating-app culture and overall virtual communication. There’s no shortage of screen-captured material, between the interfaces of fictitious dating apps, smartphone-text conversations, and video calls. The emphasis is on how all of these new touchstones have warped courtship rituals in several ways, but not entirely.
Largely predictable in most of its big movements, nothing happens, plot-wise, that you can’t at least predict from the start. The surprises are found in smaller moments within those expected beats: when characters break through the digital haze, call each other out, zero in on mistakes, flaws, and quirks. The tonal shift should be jarring but it actually draws you further in. Much of this is owed to Reale and Young-White’s performances. Very often you can feel the improvisational influence from the actors. If it isn’t improvised, then it’s deftly written to feel that way, to a pleasant result. Standout performances by Catherine Cohen (The Lovebirds) and Brian Muller (Holly Star) as Jessie and Hank, respectively, the main characters’ best friends who nearly steal the show. Nearly.
However interesting the path, it leads to an ending that follows a template, inspired by its predecessors, of traditional genre conventions, with no new ground broken. That may bother some viewers, but in some ways, it also makes the film feel a bit timeless and certainly true to form. Ultimately, if you’re expecting something more innovative, this may not be for you; but if you’re prepared to settle in for something more dependable, Dating & New York is likely right up your alley.