Three relationships. Three disasters. One last chance.

Definitely Maybe focuses on the story of Will Hayes, a 30-something Manhattan dad, who is in the midst of a divorce when his 10 year-old daughter, Maya, starts to question him about his life before marriage. Maya wants to know absolutely everything about how her parents met and fell in love and so Will accordingly tells her the story of his three previous loves, but keeps Maya's mother's identity a secret so she can guess who he went on to marry. 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 in a "PG" fashion. As Maya learns the stories behind each of the women her father had relationships with she begins to wonder if her mother could be Will's college sweetheart, the dependable girl next-door Emily ? Or is she his longtime best friend and confidante, the apolitical April? Or is she the free-spirited but ambitious journalist Summer. As Maya puts together the pieces of her dad's romantic puzzle, she begins to understand that love is not so simple or easy. And as Will tells her his tale, Maya helps him to understand that it's definitely never too late to go back... and maybe even possible to find a happy ending.