Close this search box.

Dating & New York: Film Review

A love story for the age of social media, Dating & New York is a witty exploration of the disconnected nature of an ever-connected world. 

Dating & New York takes the typical, tired, boy meets girl narrative and places it firmly in the here and now. With excellent performances across the cast and no shortage of well-timed humour, this film puts modern-day romance under the microscope. Revealing the dysfunctional reality of a world that has forgotten its humanity, Dating & New York is clever, insightful, and, above all, entertaining.

‘In a land of crowded subways and dollar pizza,’ we meet Milo (Jaboukie Young-White), a five-foot-ten (which really means five foot eight) dating app veteran looking for love. Then there’s Wendy (Francesca Reale) who’s had her fair share of heartbreak and is firmly opposed to serious romantic commitment. The unlikely pair go through the motions of a typical modern-day date: they meet online, hit it off, spend one night together, and then ghost each other entirely. As the film unfolds, Milo and Wendy reconnect and decide to enjoy all the positives of a relationship (regular sex and an emotional connection) without actually being in a relationship. Something they both believe is ‘famously, hell on earth’ and will inevitably end in heartbreak. Spoiler alert: Milo and Wendy eventually end up together, but all we saw that coming. It is a rom-com, after all. But the circus of the dating world we see on the way to happily ever after showcases an insecure society terrified of entrusting their heart to anyone.

In a world where everything is a potential Instagram story, Dating & New York brilliantly showcases the realities of the filtered world we try to present, and the fallout when the mask inevitably slips. Hank (Brian Muller), Milo’s best friend, berates Milo for saying he’s going to marry every girl he ever meets on the off chance it actually happens, all in the hope of an insta-worthy wedding speech. The pressure to have a picture-perfect relationship weighs heavily on Milo who, despite his impeccable humour and unbothered demeanour, struggles with mounting insecurities. In part a hopeless romantic, Milo subtly attempts to convince Wendy a conventional relationship wouldn’t end in heartbreak, which Wendy promptly shuts down. Wendy’s commitment issues come through in a conversation over ice cream where Wendy, who picks multiple flavours, laughs at Milo’s choice of plain vanilla. The ice cream symbol is a well-developed representation of an overstimulated society that has been taught to always want more. The film illustrates how stretching in all directions at once is more conducive to paralysis than progress: as Milo says, ‘You’ll never get to experience the joy of committing to something’.

loud and clear reviews Dating & New York
Jaboukie Young-White as ‘Milo’ and Francesca Reale as ‘Wendy’ in Jonah Feingold’s DATING & NEW YORK. (Courtesy of IFC Films. An IFC Films Release.)

Young-White gives an excellent performance as Milo, a complex character who seems to bridge the gap of generations. Milo ultimately desires a committed relationship but gets wrapped up in the social media circus it seems to take to get there. ‘Katie 7f’ (Sohina Sidhu), an old flame of Milo’s, tells him he has a ‘sick obsession with social media and what people think of him’ when he is upset she didn’t feature him on her Instagram, insisting that ‘actions speak louder than captions’. But later, in a tender scene of Milo alone in the shower, we see a young man battling insecurity, in desperate need of reassurance. A raw moment of vulnerability amongst the humour of the film is perhaps a symbol of young people everywhere, a vulnerable demographic in need of validation that instead distracts itself with cat videos and too many hours on TikTok. 

Jonah Feingolds’ directional debut isn’t a great film because of its originality or plot twists. Let’s be honest, we know what’s going to happen before it’s even started. But what is different about the film is its searing honesty, perfectly toeing the line between cinematic escapism and incredible relatability. Dating & New York examines a society obsessed with finding love but terrified of keeping it, clever direction and a few well-expressed metaphors reveal the reality of a demographic paralysed by the pressures of modern-day dating. In a scene between Milo and Hank, the two stand on a subway platform, Milo attempting to convince Hank not to call Jessie, (Catherine Cohen, who is brilliant throughout the film), a girl he just met. Milo explains how you can’t just call someone you like, even if you told them you’re going to, as the advertisements lining the subway station showcase an online pharmacy business that will ‘text you back right away’. This is just one example of the film’s clever direction, which throws the cracks in modern communication into full focus. It’s easier to access medication and artificial remedies than it is to get a text back, the landscape of modern dating is looking pretty bleak.

The film really leans into its iconic New York setting, implying that only in New York could this bizarre, dysfunctional love story have come to pass, frequently resorting to the explanation of ‘only in New York’. But it’s not a New York thing, it’s a people thing. We’re all living in a world where you have a deeper connection with a targeted Instagram ad than with your latest Tinder match. We’ve all played the long game of waiting at least an hour to reply to someone, even though we’ve been waiting by our phones for a text. And we’re all now aware that appearing on someone’s socials is a legitimate step in a relationship. In a society moulded by bizarre rules and hyper-connectivity, Dating & New York asks us to let go of all that for a second, to put your phone down, to focus on just the present moment, to pick just one ice cream flavour. For a society existing in a permanent state of digital overload, this message is incredibly pertinent: will we listen? Probably not. 

Dating & New York opens in select US theaters and everywhere films are rented digitally on Friday, September 10, 2021.

Dating & New York: Trailer (IFC Films)
Thank you for reading us! If you’d like to help us continue to bring you our coverage of films and TV and keep the site completely free for everyone, please consider a donation.