Summer 1999: Sawyer is striving to make it in New York. Between her assistant job in publishing and her upcoming wedding, it feels like the perfect life could fall into place at any moment. There is only one problem: Sawyer's fiancé has been working longer hours .

. . with an all-too-close female colleague, Kendra.

When Kendra's boyfriend, Nick, invites Sawyer to meet up and compare notes about their suspicions, the meeting goes awry. She finds Nick cocky and cynical, and he finds her anxious and overwhelming. But when Nick seeks out Sawyer to apologize, a friendship develops.

Over the summer, Sawyer and Nick start an unofficial ritual exploring New York City and they soon both begin to live for their Friday afternoons together. But what happens once the summer is over?