Definitely, Maybe (2008)

It’s never too early to romanticize the past, particularly when it involves affairs of the heart. Amid today’s app-friendly hookups, where a potential relationship is a mere swipe right away, perhaps it is inevitable that a romantic comedy like Definitely, Maybe would turn to the not-so-distant and ostensibly simpler 1990s, back when the Internet was still a novelty and people yammered on cellphones the size of coffeemakers. And, of course, it was the time of I-did-not-have-sexual-relations-with-that-woman Bill Clinton, a presidency that Definitely, Maybe deftly uses to chart the movie’s arc from idealism to disillusion.

In other words, this isn’t your run-of-the-mill romcom, which in itself is no small feat for a genre that tends to repeat itself. Definitely, Maybe doesn’t exactly break new ground, but its characters are relatable and interesting, and the movie’s take on relationships is refreshingly realistic.

We are introduced to Will Hayes (Ryan Reynolds), a New York PR consultant, on the day his divorce becomes final. That’s tough enough, but Will has an added headache when his 10-year-old daughter, Maya (Abigail Breslin), emerges from her first sex education class. Suddenly, the girl wants to know all about Dad’s pre-Mom relationships. Will is flummoxed, but eventually agrees to tell the story of the three women who were in his life back before marriage and parenthood changed everything.

What follows is a sort of romantic mystery, since Will changes the names of the women to keep Maya guessing about which one eventually became her mother: college sweetheart Elizabeth Banks, spunky copy girl Isla Fisher or ambitious journalist Rachel Weisz? (It should be noted that TV’s How I Met Your Mother, which played with a similar premise, predated Definitely, Maybe by several years.)

Writer-director Adam Brooks captures an engaging, bittersweet tone. Defnitely Maybe exhibits genuine fondness for its characters, metaphorical warts and all, and that affection is contagious.

The cast is terrific. Banks and Weisz are excellent, if underutilized, but Fisher is pure effervescence. One can easily understand why Will would fall for any of these three. Breslin is memorable without being precocious, while Kevin Kline has a memorable bit as a lecherous college professor. Still, it is Reynolds’ ambling Everyman who ultimately gives Definitely, Maybe its emotional heft.