Jonah Feingold’s Dating & New York is a quintessential romantic fairytale for the dating app generation. Beginning with watercolor painted opening titles and the classic “Once Upon a Time…” narration, the film is a fantastical homage to the Nora Ephron romantic comedies of the 1990s and a love letter to the wistful city of Manhattan when falling in love beneath its silver skyscrapers.
In a millennial meet cute, Wendy (Francesca Reale) and Milo (Jaboukie Young-White) serendipitously match on a dating app and go out on a first date. Wendy is the girl who won’t grow up and Milo is the boy who claims to know exactly what he wants. Will they end up a perfect match? After a few weeks of ghosting, Wendy and Milo meet again and decide to form a contractual partnership to mentor each other in the art of dating. In this scenario, the two are able to remain single without the feeling of being alone; a shared attempt to only experience the good aspects of a relationship while strictly avoiding the bad. Their contract even has clauses for specific terms, such as rules on cuddling or the few extreme cases where either person is allowed to mutter those three messy words: “I love you.”
Over many conversations throughout the city, we see their not-quite-friendship evolve into something that is unmistakably romantic, despite how adamantly (or not) each might attempt to extinguish any chance of a kiss in public or a nighttime video chat suggesting they are something more than friends. They now find themselves in a cyclical routine of subtle romantic offer followed by rejection, leading to a relationship that takes one step back for every two steps forward. This hesitant shift towards a romantic relationship should come as no surprise since the conventions of the rom-com genre has told us the pair were bound to catch feelings for one another eventually. Wendy’s friend, Jessie (Catherine Cohen), even lays out the full three-act structure of this kind of story right near the beginning of the movie. Dating & New York is so wonderfully self-aware that it’s purposely filled with these kinds of genre tropes. The spark of originality comes from the specific setting and people that inhabit this world.
Feingold’s dialogue and the leading performances from Francesca Reale and Jaboukie Young-White are so incredibly exact to people currently in their 20s that it’s possible some audience members outside of that range may have a difficult time connecting to these characters and many of their conversations. There is a reference to blowing on Nintendo 64 cartridges, a mention of a podcast to interview exes about “what went wrong,” and the use of the phrase “freelance relationship” to cautiously label a dating status. There is also a delightfully funny scene where Wendy and Milo use ice cream flavors as a metaphor to talk about exclusivity in their relationship. Not properly communicating about their boundaries, jealousy is evoked as they each continue talking to other people.
We also get to observe a second new relationship made up of Milo’s friend Hank (Brian Muller) and Wendy’s friend Jessie. We periodically get glimpses into their dating life as a sort of control we can use to measure against Wendy and Milo’s. However, Hank and Jessie’s relationship moves extremely quickly; they are one of those couples who somehow seem to know with full confidence that they are in love. These friend pairings allow for some of the funniest moments in the film as each pair constantly criticizes their friend’s dating game. It’s a very smart screenplay, with plenty of setups that return later on with a greater significance. There are also some soft and honest moments that sensitively speak to the current restlessness of a generation.
The film often communicates through screens. We see that adrenaline-inducing moment of deleting all of the dating apps off of your phone and the DRAMA in waiting for a daunting text message. While already cliché in most contemporary filmmaking, the screen capture technique is used here in a way that feels crucial to the overall narrative. There are story beats that completely rely on exchanges that happen over a video call or during a text conversation. There’s also an argument about how partners are tagged in Instagram posts; “Actions speak louder than captions,” Milo yells at an ex-girlfriend in a flashback. While ridiculous out of context, the film is able to accurately express how social media plays a role in contemporary dating life.
There are many moments of fantastical sounds and imagery scattered throughout the film. The magical and jazzy score helps to set the mood, while exaggerated musical phrases are often used to heighten our experience of a character’s emotions. We see metaphorical signs that come from actual subway station signs, a makeshift therapy session that appears on the sidewalk, and an interview inside someone’s head. While mostly successful, some of these more stylistic choices do come and go throughout the film in a way that can be jarring. It’s easy to forget about the film’s narrator for a while, but then he’ll pop back in and slightly interrupt the stylistic flow of the film. It definitely takes some time to get acclimated to the film’s tone and some audience members may never get there.
Dating & New York will have a very polarizing reaction depending on whether or not a viewer is able to find a part of themself in these characters. In most cases, it’ll be because they are this age at this moment in time. The film likely won’t play well for people outside of those parameters, but this also isn’t necessarily made for them. The content is so esoteric that its specificity rings so truthful to those who have or are presently experiencing these feelings. As Wendy says, “art is art because it makes us feel something.” There are people who are made to love this film, just as this film was made for those people to love.
If they can find each other, it’ll be a perfect match.
