Among the romantic comedies that premiered during this year’s Tribeca Film Festival, Jonah Feingold’s Dating & New York mixes modern humor with traditional tropes.
While Milo (Jaboukie Young-White) and Wendy (Francesca Reale) initially succeed on a dating app, they immediately cease contacting each other. Milo and Wendy start dating and within a few weeks of their first date, Wendy texts him to meet so that they can discuss important matters. When Wendy and Milo meet in the diner, Wendy asks Milo if he’d be interested in signing a “Best Friends With Benefits” contract, where he’d receive the benefits of being in a relationship without really being in one. Milo eventually signs the contract despite the fact that he is seeking a serious relationship, while Wendy is not. Even though both are searching for totally different things, Milo nevertheless signs the contract.
Following this, they embark on a roller-coaster ride of love and friendship, navigating many advantages and pitfalls along the way. They start acting more like a real couple as the time goes by – talking about random topics at the movies, sitting in the same booth at restaurants, and even arguing over the smallest things in front of their friends. A trope already overused in romance comedies, “will they or won’t they,” is constantly used in this movie. In the movie almost everyone taunts Milo and Wendy about how they act like a couple. This goes on during Dating & New York from Milo’s family and Wendy’s best friend. It has all the elements of a great romantic comedy, including corny jokes, fun themes, and a great romance. In reality, it is quite the opposite.
Instagram, online dating, and references to technology abound, but the script never feels natural or convincing. In addition, Dating & New York looks like it’s plucked from an Adam Sandler movie from the 2000’s, when it’s actually about dating in the modern age. It’s narrated in an awkward manner, its visuals are quirky but ineffective, and the title cards are tired.
The pacing of Dating & New York is another problem. There isn’t enough time for Milo and Wendy to form a strong bond in the first act, so the film moves too quickly. There are many scenes in the film in which content and tone are so similar that they appear like one. Millennial-specific humor and an overreliance on supporting characters makes the film less engaging than comedic, and above all, tiring. It’s impossible to relate to anything that is happening on screen once the film’s final act begins.
Despite its flaws, Dating & New York is rescued by its performances. Jaboukie Young-White, a familiar face on Twitter and a correspondent for The Daily Show, excels as Milo in his first leading role. Bringing his sarcastic yet good-natured nature to life on screen is the perfect display of his lighthearted nature. As a performer, Reale nails her character’s breezy tone perfectly, naturally setting herself apart from Young-White and complementing the latter in a very pleasing manner. It’s disappointing that a film did not match their comedy abilities because of their chemistry.