But it is the women in Will’s life — including Breslin — who make up the affectionate, unsentimental heart of the film. Fisher in particular enlivens every scene she’s in with a comic energy that’s antic and graceful.
“Darlin’ you can’t love three,” says an old folk song, and in movies of this kind the man who does is likely to be viewed as a cad. Either that, or the women he doesn’t end up with will be shown to have such egregious flaws that their rejection will come as a relief.
Emily, Summer and April are all decidedly imperfect, but Brooks succeeds in showing how their shortcomings are, especially at first, part of their allure. He also makes clear that Will, besotted with each in turn, does not know any of them as well as he thinks he does. He also is not quite sure what he wants. The treachery of love — and also its promise — is that people can surprise you.
And so can movies. I’ve been known to complain about the abysmal quality of contemporary American romantic comedies, which forsake intelligence, individuality and emotional risk for crude sex jokes or gauzy bridal-magazine fantasies. While Definitely, Maybe is hardly perfect, it navigates the choppy waters of modern courtship with commendable, understated honesty. Perhaps the best evidence of this is that this movie, unlike almost every other Hollywood tale of New York singles, was actually filmed in the city.
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