A political consultant in the midst of a bitter divorce attempts to delicately divulge the truth about his past relationships to his curious young daughter, who simply won't stop asking questions until she's satisfied with all the answers. Ten-year-old Maya (Abigail Breslin) is heartbroken to see her parents splitting up, but she's determined to find out precisely how it was that mom and dad came together in the first place. When Maya starts questioning her father Will (Ryan Reynolds) about his life before marriage, dad's memories soon drift back to the time when, as a naïve Wisconsin native and aspiring politician hoping to work on the presidential election, he first arrived in New York City. As Will gradually became savvy to the ways of the big city, he gradually developed romantic relationships with three very different women: Emily (Elizabeth Banks) was the girl-next-door that he could always depend on, apolitical April (Isla Fisher) was the best friend and confidante who was always there to listen, and free-spirited journalist Summer (Rachel Weisz) was both beautiful and ambitious. In order to prevent his perceptive little girl from predicting the outcome before his story is told, Will carefully changes the names of his three romantic interests, creating a hopelessly romantic puzzle that highlights both the joys and hardships of true love.