In the world of film, there are few places as perfect to fall in love as New York City. In Moonstruck, New York is a magical place where love makes people do crazy things. In When Harry Met Sally…, it’s the everyday backdrop for a slow-burn evolution from friends to lovers. In Sex and the City, it’s the glamorous fantasy playground for a group of sexually-liberated women to sew their wild oats. Now, joining that long tradition is writer-director Jonah Feingold’s Dating & New York, a neurotic, witty, post-modern rom-com about the millennial dating scene.
It stars Jaboukie Young-White and Francesca Reale as Milo and Wendy, respectively, who meet on a dating app called MeetCute, share a one-night stand and then ghost each other for a few weeks before entering into a friends with benefits agreement that leaves both struggling to not catch feelings. Milo and Wendy want very different things. The latter is commitment-phobic, Wendy wants the consistent sex and friendship that comes with a boyfriend but without the emotional attachments. Milo, on the other hand, seems like a romantic. He insists they include cuddling in the inevitable relationship contract Wendy crafts for their relationship. What eventually happens to them probably seems inevitable to anyone who’s ever seen a rom-com, but while Dating & New York is often funny, it never quite convinces the audience that it’s doing anything but going through the motions.
Take Milo. From the opening, app-based montage, we see that he says he’s looking for “true love’s kiss”. But then, he also has multiple dating apps downloaded and during his first date with Wendy, he explains that he often falls in love with an idealized idea of the women he dates only to be disappointed when he realizes they’re real people. Perhaps it’s more accurate then to say he’s in love with love, but if that’s true, why does he seem to be fundamentally uninterested in making that kind of connection?
During the period when Milo and Wendy ghost each other, he attends a party with his friend Hank (Brian Muller) and sees a beautiful woman sitting at a bar (Taylor Hill). Frank encourages Milo to tap her on he shoulder and say something witty, but when Milo approaches her, he awkwardly punches her on the shoulder instead. It’s a funny moment and one that’s meant to suggest Milo has no game. It works. What doesn’t is what happens a few moments later, when the woman casually drops that she has a boyfriend and Milo immediately walks away, not even bothering to politely end the conversation. Though that sudden turn makes sense with Milo’s relentless, self-centered pursuit of love, he later shows the same emotional volatility and pettiness during a break up with a woman from his building who he’s casually seeing.
Now, one could argue that the disconnect between what Milo says he wants and what he actually strives to get are part of the film’s commentary—he wants a relationship, but lacks either the emotional maturity or the will to put the work into maintaining one. However, once he and Wendy make their arrangement, Milo is suddenly hyper-focused and almost immediately in love, willing to do and endure just about anything to keep alive the chance of dating Wendy for real. Unfortunately, he and the film stay in that unsure limbo state for much of the runtime and Dating & New York is forced subsist largely on its charming cast rather than its story or characters.
Though Milo is occasionally obnoxious, Young-White’s natural charm keeps him from becoming hatable and he and Reale banter well together. They’re also surrounded by a who’s who of talented New York comedians, from Alex Moffat as a shallow finance bro Wendy briefly dates to Eva Victor as an aloof rebound who breaks up with Milo on the subway, leaving him to attend a John Mayer concert alone. Best of all, though, are Muller and Catherine Cohen as Milo and Wendy’s respective best friends. The couple also meets cute at the same party where Milo so rudely abandons the girl with the boyfriend and their romance develops on the film’s fringes. While their arc is more the traditional rom-com fare, they are also more compelling in a way Milo and Wendy simply aren’t.
Perhaps it’s because Cohen and Muller get to play more confident characters or perhaps they’re just a little better at selling their underwritten characters’ overwritten dialogue than the leads. But there’s also just something more interesting and perhaps even realistic in their frankness. Jessie and Frank like each other immediately and while they are just as ironic as Milo and Wendy about love, they’re also better at softening that wit with genuine romance. Yeah, maybe their easy progression is idealized, but they still somehow come off more like actual human beings than cynical caricatures about dating like Milo and Wendy.
What ultimately keeps Dating & New York from feeling like a fully-realized film rather than a collection of loosely-related comedy bits is the same thing that keeps Wendy and Milo from taking the next step: it clings too tightly to looking at romance with a self-protective, wry sense of humor to take the risk of feeling something real. There is truth in the way Feingold relates the absurdity and aimlessness of modern dating, but in only ever using its characters as amusing but empty pieces in a send up of rom-com tropes, Dating & New York ultimately misses the truth underlying all of Milo and Wendy’s self-sabotage. We subject ourselves to the potential embarrassments of dating because human connection is worth the risk. Sure, there’s cleverness in acknowledging how silly people in love can be, but there’s no bravery in staring disappointment in the face without admitting that love can also be truly, unironically important.
