In the bustling, swipe-right world of modern romance, two young New Yorkers attempt to engineer the perfect low-stakes relationship in the charming comedy Dating & New York. After a promising first date, pragmatic Wendy (Francesca Reale) and idealistic Milo (Jaboukie Young-White) make a pact to become "best friends with benefits," complete with a meticulously crafted set of rules designed to avoid the messy pitfalls of love. Their clever arrangement seems foolproof, allowing them to enjoy companionship without commitment, all while navigating the opinions of their eccentric friends, including the perpetually single Catherine Cohen. Yet, as their lives intertwine over subway rides and city adventures, the carefully drawn lines between friendship and something more begin to blur, testing their original agreement. Directed by Jonah Feingold, this witty and heartfelt film captures the anxieties and absurdities of looking for connection in the digital age, asking if a contract can ever truly govern the human heart.