Regardless of neighborhood, profession or intended rendezvous location, clothing has long been an inseparable lifeblood to success and failure when dating in New York City. A Manhattan native, director Jonah Feingold has long felt inspired by the city’s historic sense of style, especially as it overlaps into the treacherous waters of romantic pursuits.
In his debut feature-length film, "Dating & New York", Feingold depicts the dating scene of his hometown as a fantastical hellscape. The film follows the “situationship” between its two leads, Wendy and Milo, along with all of the trivial parts of dating in modern-day Manhattan. Today's dating culture unfolds through an app called “Meet Cute” where men lie about how tall they are and the nuances of being “friends with benefits” weigh on users who cautiously dip their toes into the realm of something more.
The film exaggerates many classic rom com tropes like charming diner dates, fairytale-like storytelling and, nonetheless, dating fashion. One garment in particular, the turtleneck, was inspired by Feingold’s all-time favorite rom com outfit: the legendary white sweater and jeans worn by Billy Crystal in "When Harry Met Sally".
Styling the characters in "Dating & New York" was the result of collaboration between Feingold, the movie’s stylist Hope Fourie, and production designer Michelle Li. The three worked on a tight budget to bring personality to the characters through clothing while being sure every outfit had a purpose.
Alongside the many turtlenecks, a pair of overalls worn by Wendy during a diner date also held special significance.
“There was a section of time where my Hinge profile said, ‘just looking for a girl wearing overalls on the subway,’” Feingold recalls about writing the garment into his script.
In this same scene, Wendy also wears a ribbon in her hair as a tribute to the character from Peter Pan of the same name — all of this being a clever nod to her love of fuckboys, the real-life lost boys of modern dating.
Feingold’s personal wardrobe also made an appearance in the film by way of a last-minute casting issue that brought the director in front of the camera to play Mort, a case study date failure. For the scene, Mort has his second date hopes rejected while sporting a penguin intarsia knit sweater from Feingold’s closet.
When it comes to putting together the perfect outfit for behind the camera, Feingold likes to keep a few important factors in mind. First is comfort, seeing as long shooting days don’t often leave time for wardrobe changes. He notes style is also important, however, mainly due to the possibility of a behind-the-scenes picture being snapped on set. Finally, he likes to consider approachability when putting together his outfit so his fellow crew members feel comfortable coming up to him and offering their ideas and opinions. He also mentions the importance of pockets in order to hold all the things you may need on set.
His ideal outfit is cool pants, a t-shirt with cuffed sleeves, and sneakers. The Instagram @directorfits is something he references and points out the constant posting of 1990s directors wearing Hawaiian shirts. Jonah wonders if this plays into the idea that a director should be approachable on set. He is still searching for his director fit staple, the way Wes Anderson has his Clark’s Wallabees and Steven Spielberg has a big 90s baseball hat and sunglasses. Ultimately, Feingold defaults to dressing along with the cast, often opting to dress as if he’s in the scene.
Some of the most cherished items from Feingold’s personal wardrobe are a collection of Disney-related merchandise he has gathered over the years. He pegs a vintage baseball cap from the 1995 New York premiere of "Pocahontas" as his favorite clothing item. The premiere took place in Central Park and the merch was made in collaboration with the city’s Parks Department. Another item he has an emotional connection to is a 1997 Hercules cast and crew sweater from a "Dating & New York" producer who promised him if he sold the movie he could have it (it is important to note that Jonah is NOT a Disney adult). He is also currently seeking out a 1980s USC film school hat to add to his collection of movie merchandise.
Aside from being a writer and director, Feingold admits he has accidentally earned himself the title of Dating Guru. During the process of drafting "Dating & New York" he also co-hosted a podcast sponsored by the dating app Hinge. For a first date, he likes to wear a t-shirt with a cuff sleeve (maybe this is his staple) tucked into trousers along with some boots — something comfortable and loose altogether. For a second or third date with someone he really likes he’ll typically opt for a nice sweater. When asked about his preferred breakup outfit, he said he’s never been able to plan one.
When talking about his style icons, Feingold unsurprisingly gravitates towards movies. Within the rom com genre specifically, he again underscores "When Harry Met Sally" and also notes that Hugh Grant just looks good and cool in anything. As far as his real-life inspirations, he’s influenced by Fran Leibowitz, his dad’s closet, and the men’s fashion podcast Throwing Fits. With all three of these being New York staples (his dad grew up in this city on this same block Jonah lived on with his family), Jonah told me about how Manhattan has influenced not only his personal style but the look of his movies as well. He waxed poetic about how witnessing everything going on around the city feels like watching movies in real time, wondering out loud how someone could come here and not be inspired.
“You can point the camera anywhere you want and the personality speaks through,” he declared. “There’s a reason that some of the greatest movies in the world take place here”.
"Dating & New York" is available to rent now on YouTube and Amazon Prime.
