Will Hayes (Ryan Reynolds) is a soon-to-be-divorced advertising executive. The highlight of his week is when he gets to pick up his middle school daughter Maya (Abigail Breslin) from school. One afternoon, the school is an uproar after a particularly graphic sex education class and in an attempt to calm his daughter, Will tells the tale of how he met Maya’s mother, complete with a few romantic interludes as well.
Elizabeth Banks, Rachel Weisz and Isla Fisher play Hayes’ three love interests, in what are mostly flashback scenes which tell the romantic history as a slowly revealed mystery. This device seems to have worked for the long running TV show, How I Met Your Mother. But, here it just feels tedious. Each of the three great loves of Will’s life are interesting in their own way, but the way the story moves from one to another lacks surprise or real emotional energy.
In fact, there’s a kind of recycled romantic dynamic that permeates the whole film. All the main characters, and especially Banks as a nearly-neurotic WASP-ish beauty, Weisz as the dark, brooding intellectual & Fisher as the fun, carefree redhead have played more compelling versions of exactly the same kind of characters in other films. Definitely, Maybe is not a bad film, but positively, absolutely is not special either.