Will Hayes (Ryan Reynolds), thirty-something with a successful job in something or other in a high rise in mid-town New York, is in the midst of a divorce. When his ten-year-old daughter Maya (the lovely Abigail Breslin) asks to hear the true story of how he met her mother, he obliges by coming up with the film's narrative conceit on the spot. He tells the story, changing "all the names and some of the facts" to make the identity of Maya's mother unknowable for at least 120 minutes, and incidentally, the subject of the most detailed bedtime story ever told. The college sweetheart (Elizabeth Banks), the confused yet endearing nonconformist (Isla Fisher) and the smoldering intellectual (Rachel Weisz) flow in and out of Hayes' romantic history with expressive ease.
The "love-story mystery" trumpeted in the production notes is not much of a mystery, as Hayes' relationships with the three women take predictable turns involving mistrust, heartbreak and attraction, but the central love story is at least developed in a reliable way. Writer-Director Adam Brooks's 1995 screenplay French Kiss was more successful in happily engaging the viewer in humorous conflicts of emotion that led faithfully to the promised kiss at the end. The opening scene of Definitely, Maybe is difficult to watch without contemplating the more boring moments of one's life. There is, however, something fresh in the film's payoff, owing to Brooks' adequate script and perhaps to the actors' abilities to win us over with their persistence. The film's time-line, which begins with the 1992 election of Bill Clinton (Hayes is a young staffer for the campaign in New York) and continues to the present day, is annoyingly peppered with 'Come As You Are; and television clips of Monica Lewinsky, Gennifer Flowers and Bill himself, which seem unrealistically aimed at garnering cheap laughs at the way we were.