The movie begins with the eight-year-old wanting to know how her father met her mother. Will agrees to share the story, but changes the names and the places, creating a “romantic mystery” the little girl must unravel. For the next couple of hours Will unwinds a bedtime story of love lost and found complete with all the gossipy details. It’s an interesting framework for a romantic comedy, and, aside from the questionable practice of an adult sharing the details of his sexual history with a youngster, this romantic Rashômon works very well.
With Maya hanging off every word, and even making up flow charts to keep track of her father’s various involvements, Will works through his romantic life, starting with his college sweetheart Emily (Elizabeth Banks), right up to his big city crushes, the sexy and free spirited Summer (Rachel Weisz) and the edgy April (Isla Fisher). There are ups and downs along the way—one woman tells him that they shouldn’t date because they’re like “Lennon and McCartney… Good while they lasted but afterwards they couldn’t even be friends”—and even though he tries to present a PG version of the story, he still occasionally gets down and dirty with the details.
The romantic escapades are woven in amongst a timely parallel story of Will’s involvement with the Clinton—Bill Clinton, that is—campaign in 1992.
In recent years the romantic comedy genre has suffered from a bad case of predictability. Most often you know how they going to end before they even start, so it is the journey, how the characters end up in a loving embrace at the end of the film that matters. Definitely, Maybe’s storytelling structure is a different take on the tried and true formula and while it does have a happy ending—it has to otherwise it would be a romantic tragedy!—the twist adds some life to an otherwise moribund genre. It’s a rom com for grown-ups; a little more realistic than most (although just a tad more realistic), with a welcome bit of edge.
Like all good romantic comedies Definitely, Maybe is set in New York, and has some genuine laughs, mostly bolstered by a charming cast led by Reynolds, whose chemistry with the women and Breslin seems real and unforced. His sense of timing is bang on, and his way with physical humor works here—a subtle sight gag that sees him, with his big hands, drinking from a tiny juice box drew laughs and awws from the audience I saw it with—and since he is in every scene, it’s ultimately his charisma that carries the movie.
Definitely, Maybe still has most of the predictable elements found in many movies of its genre, but is heartfelt and just different enough to earn a recommendation.