Once upon a time in the magical kingdom of New York City, a city that doesn't sleep but sleeps around a lot, a land of the best pizza in the world and crowded subways, two single millennials Milo (Jaboukie Young-White) and Wendy (Francesca Reale) find each other through the Meet Cute dating app. After a one-night stand, the magic of New York brings them back together, and they draw up a “Best Friends With Benefits” contract to avoid the pitfalls of a relationship. Will friendship and sex mix without any complications? With the help of Cole the Doorman (Jerry Ferrara) and their friends Hank (Brian Muller) and Jessie (Catherine Cohen) who are also dealing with their own complications of a new relationship, Milo and Wendy just might find what they’re looking for.