Oliver and Cassi have been together for five years. With their lease up for renewal, and neither one of them capable of paying for the apartment on his or her own, Oliver and Cassi have to decide whether or not to renew their lease and commit to living together for another year, or call it quits and move out. In order to gain perspective and clarity, Oliver and Cassi have taken two weeks apart: He remaining in their Brooklyn Heights apartment; She at her sister’s on the Upper West Side. The story begins when each of their respective best friends, Max and Letty, spends the day with them, meandering the city, attempting to help them each find clarity, in order to make what might be the most important decision they have ever had to make.