Jun 16, 2021
By Kaveh Jalinous
Jonah Feingold’s Dating & New York is a well-intentioned but uninteresting romantic comedy that attempts to mix traditional genre norms with millennial humor. The film follows Milo (Jaboukie Young-White) and Wendy (Francesca Reale), two single twenty-something-year-olds who meet on a dating app and hit it off, only to instantly stop contacting, or “ghost,” each other. Several weeks after their single date, Milo receives a text from Wendy out of the blue, asking him to meet her so they can talk over “urgent” matters. The two meet at a diner, where Wendy asks Milo if he’d be interested in signing a “Best Friends With Benefits” contract, meaning all the sexual and friendship benefits of a relationship without the relationship itself. Even though the two are searching for something completely different – Milo is looking for a serious relationship while Wendy is looking for anything but – Milo eventually signs the contract.
From here, the two go on a roller-coaster journey navigating the various advantages and pitfalls of both love and friendship. As they spend more time together, they start acting more like an actual couple – connecting over random topics while at the movies together, sitting on the same side of the booth at restaurants and even dramatically fighting over the smallest things in front of friends. The film constantly tries to pull off the “will they or won’t they” trope that is already overused in romantic comedies. Almost everyone else in the movie, from Milo’s doorman to Milo’s and Wendy’s best friends, constantly taunts the two about how “couple-like” they seem.
Meant to be corny but fun, Dating & New York has all the trappings of a successful romantic comedy. Unfortunately, it is anything but. The script, crammed with enough Instagram, online dating and technological-era references to make you want to throw your phone down a trash chute, rarely feels natural or believable. Plus, for wanting to be a film about dating in the modern age, the stylistic aspects of Dating & New York feel as if they were plucked out of a film from the 1990s. The film’s dramatic and overused narration, quirky yet unsuccessful visuals, and tired sitcom-style title cards lose their charm very quickly.
Moreover, Dating & New York suffers from pacing issues. The film moves way too quickly in the first act, and as a result, is unable to cement a strong enough bond between Milo and Wendy. All of the film’s scenes are so similar in content and tone that they practically blend together. An over-reliance on supporting characters and hyper-specific millennial-targeted humor keeps the film more cringe-worthy than comedic, and above all, tiring. By the time the film’s final act commences, nothing that is happening on-screen feels remotely believable anymore, let alone relatable.
The one redeemable part of Dating & New York is the film’s performances. In his first leading role, The Daily Show correspondent and famed Twitter personality Jaboukie Young-White gives a fantastic performance as Milo. He perfectly captures the sarcastic yet good-natured tone of his character with his natural and lighthearted screen presence. Reale’s performance is great as well, nailing the breezy tone of her character in a way that makes her both stand out from and perfectly complement Young-White’s performance. The two’s incredible chemistry only makes it more frustrating that they weren’t given a film strong enough to match their comedic abilities.
Author rating: 4/10
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