A successful investment banker with a beautiful, intelligent wife and two gorgeous kids at home, Richard Cooper (Chris Rock) would seem to have it all. However, between the daily commutes from the suburbs to New York City, the endless business meetings, the kids' diapers, and the Wiggles on TV, there's only one thing on Richard's mind: women. The women he sees on the commuter train in the morning, the women who walk the streets of Manhattan, the women he fantasizes about in order to alleviate the boredom of his mundane routine life. Happily married to Brenda (Gina Torres), Richard has no intention of cheating, until an old friend, the stunning Nikki (Kerry Washington), appears at Richard's office door, asking for help in landing a job. During lulls in his workday, Richard starts meeting Nikki for late lunches, and the banker's conventional life begins to turn upside down.