Dana grew up in a small town with her sights set on New York romanticizing about the life and love it had to offer while Peter, by contrast, grew up there and feels like he has been there and done that when it comes to life in Manhattan. Dana is determined to succeed in New York in both business and love, while Peter is perfectly content to go on dating his way through it. While it is the streets of New York that offers this duo a first glimpse of each other, it's family and friends who conspire to set them up. The audience will go along for the ride as they venture on their first date and hear exactly what they really think of each other.

Dana and Peter seem to have reached the perfect relationship balance - they've jointly agreed to see other people but not talk about it. But their dating anonymity is all about to change when Dana learns of a long-standing dinner party Amy is hosting at the loft - and the fact Peter is attending and bringing someone else as his date. On a mission to find her own suitable dinner companion, Dana turns to her new handsome and British boss, Tucker, but both Peter and Dana's evenings do not go as planned.