Review: ‘Dating & New York,’ starring Francesca Reale, Jaboukie Young-White, Catherine Cohen and Brian Muller

September 24, 2021

by Carla Hay

Jaboukie Young-White and Francesca Reale in “Dating & New York” (Photo courtesy of IFC Films)

“Dating & New York”

Directed by Jonah Feingold

Culture Representation: Taking place in New York City, the romantic comedy “Dating & New York” features a predominantly white cast of characters (with a few African Americans, Asians and Latinos) representing the middle-class.

Culture Clash: After meeting through a dating app, a man and a woman in their mid-20s decide to become “friends with benefits” until one of them falls in love with the other person and wants more of a romantic commitment. 

Culture Audience: “Dating & New York” will appeal primarily to people who are interested in overly talkative romantic comedies that are extremely formulaic and not very funny.

Jaboukie Young-White and Francesca Reale in “Dating & New York” (Photo courtesy of IFC Films)

“Dating & New York” is proof that the only thing worse than a dull and unoriginal romantic comedy is a dull and unoriginal romantic comedy that thinks it’s exciting and creative. This annoying movie reeks of smugness, when it’s really just a worse version of the mediocre 2011 romantic comedies “No Strings Attached” (starring Ashton Kutcher and Natalie Portman) and “Friends With Benefits” (starring Justin Timberlake and Mila Kunis). Each of the three movies is about two good-looking young people who have a sexual relationship while trying not to fall in love with each other. However, “Dating & New York” (written and directed by Jonah Feingold) takes it to irritating levels by trying to be too cute for its own good.

How cutesy does “Dating & New York” want to be? In the very beginning of the film there’s a voiceover narrator (a role played by Jerry Ferrara) and animation (as if this a Disney fairytale), with the narrator saying this monologue: “Once upon a time, in a magical kingdom known as New York City, in a city that doesn’t sleep, but sleeps around a lot, a land of dollar pizza and crowded subways, there lived two millennials cursed with the paradox of choice.”

Side note: A pizza slice that only costs a dollar in New York City? What year was this screenplay written? Anyone who’s spent time recently in New York City can spot the phoniness of the “dollar pizza” line because it’s been several years since a slice of pizza in New York City cost only one dollar.

Viewers soon find out that the story’s two central characters, who are both in their mid-20s, aren’t very cursed at all and are actually quite spoiled and privileged. These two don’t have much “paradox of choice” struggles going on, unless you consider it a “paradox of choice” when they have to decide what kind of attitude they want to have in any given hour: self-pitying whiner or self-absorbed hipster. You get the feeling that Feingold wrote the characters this way because he knows a lot of people who think of themselves as adorable and funny, but they actually lack self-awareness in how insufferable they are with their entitled and out-of-touch attitudes about what life’s real problems are.

Milo Marks (played by Jaboukie Young-White), who was born and raised in New York City, lives rent-free in the spacious and modern Upper West Side apartment of his mother and her boyfriend, who aren’t home very much because they travel a lot for their jobs. Milo doesn’t seem to have a job. However, the movie shows that he’s an aspiring stand-up comedian with no talent who can only get occasional gigs performing in small places with hardly anyone there to see him. Here’s a sample line from his stand-up comedy act when he talks about romantic relationships: “Rollover feelings are like rollover minutes.”

Wendy Brinkley (played by Francesa Reale), who becomes Milo’s “best friend with benefits,” isn’t shown working at all. She’s got loads of snappy one-liners and comments that are supposed to show that she has a “firecracker” personality, but it’s all so superficial. The movie doesn’t even bother mentioning what Wendy does for a living or what she wants to do with her life. That’s how hollow her character is, although Reale is one of the better actors in this cast.

Milo and Wendy have met on a dating app called Meet Cute. Viewers first see Milo and Wendy together on their first date at an East Village bar called Lilo’s. Here’s a sample of their conversation: Wendy asks, “What is your baggage?” Milo answers in a sarcastic manner, “I have no baggage. Basically, I tell people I’m just like you, but perfect.”

Milo then says in all seriousness why he has problems keeping a steady relationship: “I create this fantasy version of a person … And a lot of the time, I don’t like the real person as much as the fantasy person.” Milo essentially tells Wendy on this first date that he usually ends his relationships when he becomes disappointed or bored with the person who stops meeting his fantasy expectations.

Most people with some modicum of self-respect wouldn’t want to get involved with someone who’s obviously very emotionally immature. However, Wendy is attracted enough to Milo that she sleeps with him on their first date. Milo is the type of person who says, “Only in New York can you make out with someone in front of a bunch of garbage and it’s still romantic.”

After Milo and Wendy spend the night together, they don’t keep in touch with each other for several weeks. Milo is a little surprised, but his feelings aren’t that hurt since he and Wendy don’t know each other well enough to feel like it’s a total snub. The voiceover narrator explains that Milo and Wendy both moved on and casually dated other people. Viewers find out later that the narrator is a doorman named Cole Navatorre, who works in Milo’s apartment building and ends up giving Milo some advice on Milo’s love life.

And because this is a romantic comedy that’s a cesspool of clichés, it should come as no surprise that Milo and Wendy both have best friends who end up dating each other. Milo’s best friend is an ambitious J.P. Morgan financial analyst named Hank Kadner (played by Brian Muller), while Wendy’s best friend is a fast-talking neurotic named Jessie Katz (played by Catherine Cohen), who has been Wendy’s closest confidante since they were students at Wesleyan University. Whatever Jessie does for a living remains a mystery. This movie seems to have a problem showing women with careers.

Hank and Jessie have their “meet cute” moment when Hank and Milo are at a trendy bar, and Jessie comes over to talk to them. Milo hasn’t seen Wendy in several weeks at this point. Milo spots a model-esque woman named Olivia (played by real-life model Taylor Hill), who’s sitting alone at the bar counter. Even though he hasn’t met Olivia yet, Milo says to Hank and Jessie out loud (with a lot of wishful thinking) that she’s his future wife. Jessie encourages Milo to start talking to this mystery beauty.

Milo gets the courage to approach Olivia. They introduce themselves to each other. The conversation starts off friendly and a little flirtatious, until Olivia mentions that she has a boyfriend. As soon as Milo hears that Olivia is already romantically involved with someone else, he walks away from her while she’s talking. How rude. It’s an example of how Milo thinks he’s a better catch than he really is.

After Milo abruptly cut off his conversation with Olivia, she comes over to where Milo is to scold him for being so disrespectful. It doesn’t phase him too much. What does catch him off guard is finding out that Jessie is Wendy’s best friend. And what do you know, here comes Wendy to walk into Milo’s life again. Wendy is also still single and available, the sparks are still there between Milo and Wendy, and so they pick up where they left off.

Milo soon finds out that Wendy wants a “best friends with benefits” relationship. She even makes a “Best Friends With Benefits” contract that Milo reluctantly signs. Wendy constantly lectures Milo that they’re better off not falling in love with each other because it would ruin their relationship, while Milo wants to leave open the possibility that they can fall in love. In other words, the movie shows very early on which person in this relationship is going to “catch feelings” and fall in love with the other person first.

Hank and Jessie, who have more traditional views of romantic relationships, both think the “Best Friends With Benefits” contract is a bad idea. Hank and Jessie’s romance has a typical trajectory, while Milo and Wendy’s relationship has stops, starts and some arguments in between. Hank and Jessie argue too, but not as often as Milo and Wendy have conflicts. Jessie and Hank are also the type of couple who will make up easily and end their arguments with passionate kissing. Wendy doesn’t believe in showing public displays of affection in a “best friends with benefits” relationship.

“Dating & New York” puts Milo and Hank in scenarios that try to make them look “progressive hipsters,” but it all just looks like contrived crap. For example, there’s a scene where Milo and Hank talk about their love lives while they’re at a spa, getting facials while wearing pink bathrobes and having towels wrapped around their heads. Is that supposed to make them look like feminists? It’s all so phony, because not once are Milo and Hank seen in the movie actually having a conversation with the women in their love lives about the women’s hopes, dreams and life goals, and how they can support each other in those goals.

And since this a romantic comedy with no original ideas, it uses the old cliché of ex-lovers coming into the picture so the new couple at the center of the story will be “tested” by jealousy issues. Milo’s ex-girlfriend is someone whom he calls Katie 7F (played by Sohina Sidhu), because she grew up in Apartment 7F of Milo’s building. Katie has unresolved feelings for Milo.

Wendy’s ex-boyfriend is a weirdo named Bradley (played by Arturo Castro), whom Milo and Wendy see at a plant shop. Bradley is there with his current girlfriend Erica (played by Hallie Samuels), who’s got a ditsy personality. The four of them have an awkward conversation.

And the boring scenarios drag on and on until the movie comes to the most derivative conclusion that anyone can expect. None of the actors in the cast does anything special. Reale has the best comedic timing out of all the cast members, while Young-White is sometimes stiff in his delivery. It doesn’t help that Milo is an obnoxious character who thinks he’s got a better personality than he really does. The supporting characters in the movie are very two-dimensional and trite.

“Dating & New York” has so little originality and is filled with so much annoying dialogue, you can fall alseep or fast forward through the middle of the movie, start watching the last 20 minutes, and still know how everything is going to end. If you can’t get enough of these types of predictable romantic comedies with a concept of “friends with benefits who try to pretend they won’t fall in love with each other,” then you’re better off watching a classic such as “When Harry Met Sally.”

IFC Films released “Dating & New York” in select U.S. cinemas, digital and VOD on September 10, 2021.