Maya is determined to find out how her parents first met. She also wants to know if there were any other women he was romantically involved with. The answer to that turns out to be an emphatic yes.
Will, a young man with political aspirations, moves to New York in 1992 to spend a few months working on Bill Clinton's presidential campaign.
Reluctant to be too specific, Will agrees to tell all but insists on disguising names and identities, leaving it to Maya to guess who her mom turned out to be. "A love story mystery" is how the youngster describes it, and that's the way things unfold in the film's extended flashbacks.
The trio of women in Will's life includes college sweetheart Emily (Elizabeth Banks), who fears that if Will goes to New York he will never return, and the vivacious Summer (Rachel Weisz), an aspiring journalist. The third woman in Will's life is April (Isla Fisher), a free spirit who listens to Nirvana and rereads "Jane Eyre" every year.