Will Hayes (Ryan Reynolds) is a 30-something Manhattan dad in the midst of a divorce when his 10 year-old daughter, Maya (Abigail Breslin), starts to question him about his life before marriage. Maya wants to know absolutely everything about how her parents met and fell in love. Will's story begins in 1992, as a young, starry-eyed aspiring politician who moves to New York from Wisconsin in order to work on the Clinton campaign. For Maya, Will relives his past as an idealistic young man learning the ins and outs of big city politics, and recounts the history of his romantic relationships with three very different women.