The show begins with 5 New Yorkers sharing their dating disasters ("The One"). The scene shifts to an unnamed restaurant in modern-day New York City. Aaron, a quirky man, enters the restaurant and begins to talk with the waiter. Based on how nervous he is, the waiter guesses that this is a first date. After the waiter seats Aaron, an artsy woman named Casey enters the restaurant. She spies Aaron putting in eye drops as he waits for her, making her dread the date even more; she then orders strong drinks in hopes that the date will be quick and painless. Casey and Aaron exchange some small talk and it is revealed that the date was set up by Casey's sister, Lauren, whose husband Kevin is a co-worker of Aaron's. Through the small talk, they both develop first impressions of each other ("First Impressions").
