Review - Definitely, Maybe

Definitely, Maybe is a romantic comedy with heart, but more importantly with smarts. The narrative structure, though unconventional, works well by constructing a story within the story. Will Hayes (Ryan Reynolds) tries to explain to his daughter (Abigail Breslin) the intricacies of love by relating the story of his three loves, one of whom just happens to be her mother.
The chemistry between Reynolds and all of the women in the movie is what carries the film. He is affable and goofy enough to feel like an everyman, while at the same time being notable enough to be worthy of our attention. However, screenwriter/director Adam Brooks is smart enough not to make the movie only about his romantic (mis)adventures, but also about his political aspirations, his climb up the corporate ladder and his general engagement with adulthood. Throughout the course of the film, we get to watch him grow and change and audiences really do connect and identify with him, making the emotional hits relevant and engaging, unlike other contrived romances.
That is not, of course, to discredit the impact of the three leading ladies of the film: Emily (Elizabeth Banks), April (Isla Fisher), and Summer (Rachel Weisz) who all turn in fantastic, nuanced performances. Emily is the small town college sweetheart, sweet and unassuming but she is incredibly overpowered by the performances of Fisher and Weisz. Weisz's Summer is a starving intellectual, a struggling writer for the New Yorker who's dating a famed author, two times her senior. She is obtuse and unpredictable but charming and devastatingly gorgeous, rivaled only by Fisher's April, the spunky and unpredictable copy girl who swoops in and becomes Will's best friend and steals his heart.
These three women circle like sharks throughout the entire movie, leaving viewers as confused about who Maya's mother is as she is. In many films, this would have been an annoying contrivance but Brooks structures his story in a way that makes you as invested in Will and Maya's father-daughter dynamic as you are in his romantic conquests.
The true power of the movie lies in the screenplay which is intelligent and logical and actually representative of real-life. Its few saccharine moments are believable and grounded enough to not sink the movie. The one time you think they may have gone too far and introduced a set-up far too great to be believable, Brooks manages to make it an essential part of the story which actually adds to the conflict.
The genius is that it breaks the rules of romantic comedies. There is no predestination which guides the story. There is simply the very visceral "wrong time-wrong place" of real life. Will wants to be with everyone but can't seem to be with anyone because of actual conflicts, which are organic and not forced (a welcome relief in the rom-com genre.) You truthfully don't know who Will belongs with until the last few minutes of the film but once you find out, you realize it couldn't have gone any other way. It's frustrating, painful and fraught with disappointment and joy--just like real life.