Romantic comedy: Will Hayes, a 30-something Manhattan dad 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. 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 a 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. On the campaign, Will's best buddy is Russell McCormack. They not only have similar political aspirations, they share the same type of girl problems, too. Will hopelessly attempts a "PG" version of his story for his daughter ad changes the names so Maya has to guess who he finally married. Is her mother Will's college sweetheart, the dependable girl next-door Emily? Is she his longtime best friend and confidante, the apolitical April? Or is she the free-spirited but ambitious journalist? 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.

On the day she has her first sex ed class, 10-year-old Maya grills her divorcing dad Will Hayes about her conception. That night, he fills her in, changing the names of the women who were in his life then to keep her guessing which is her mom: Emily, his college girlfriend when he came to New York from Wisconsin for Clinton's '92 campaign; April, edgy, a little cynical, who misses her father; and, Summer, a writer attracted to older, established men. In demanding the story, Maya's motivation is clear: to get her dad to fall in love again with her mom. Will this parent trap work? In the telling, might Will discover his true Penelope? Definitely. Maybe.

The students at PS322 in New York City have just had their first sex education class, which doesn't sit well with many of the parents and brings up many questions by the students of their parents, including the "gross" factor of if their parents really had sex to conceive them. But for ten year old Maya Hayes, the ultimate question becomes how her parents, Will and Sarah Hayes, met and fell in love and how that love disappeared on what is now the cusp of their divorce. Maya wants to know to figure out how to make a seemingly unhappy Will, which includes being unhappy in his current job as an ad executive, be happy again, hopefully with Sarah. Upon much coercion by Maya, Will finally relents but with one caveat and two assertions: he will change the names of the women involved so that Maya will have to figure out which is her mother, the story is not as simple as Maya would probably hope, but the story does have a happy ending. Will begins his story in 1992, when he, then politically active and fantasizing of one day becoming president, moves temporarily from his college stomping grounds of Madison, Wisconsin to New York City to work on Bill Clinton's presidential bid. The three primary candidates as Maya's mother are: "Emily", Will's college sweetheart, who is afraid that Will will never return from New York and if he does that his experience there will fundamentally change him; "Summer", Emily's New York based friend, a sexually liberated woman and professionally ambitious writer; and "April", the copy girl in Clinton's New York campaign office, she who challenges Will intellectually but who herself is unmotivated to do anything with her life. As Will's professional life rises and falls, and as Emily, Summer and April enter, exit and reenter his life, Maya continually changes her opinion on who she wants to be her mother. But as Will's story hits what Maya believes to be close to its conclusion (after a series of previous possible close conclusions), Maya believes she's figured out if Emily, Summer or April is indeed her mother. But Maya also learns that Will is correct in that the story is not as simple as a "Will/Sarah" happy ending and tries to help him find that happiness she feels he deserves.