At age 33, Penelope “Pepper” Bradford has no career, no passion and no children. Moving into the Chelmsford Arms with her fiancé Rick, an up-and-coming financier, and joining the co-op board give her some control over her life --- until her parents take a gut dislike to Rick and urge Pepper to call off the wedding. When, the week before the wedding, she glimpses a trail of desperate text messages from Rick’s obsessed female client, Pepper realizes that her parents might be right. She looks to her older neighbors in the building to help decide whether to stay with Rick, not realizing that their marriages are in crisis, too. To her surprise, Pepper’s best model for love may be a clandestine gay romance between Caleb and Sergei, a black porter and a Russian doorman.