Ryan Reynolds plays Will Hayes, a likable guy who has had some bad luck in the world of romance. As Definitely, Maybe opens, Will is in the process of finalizing divorce papers that will end his marriage.  Most crushed by his decision to separate from his wife is Will’s daughter, Maya (Abigail Breslin), who he now only gets to spend a couple nights a week with.

     Amidst the hardships caused by her parents’ separation, Maya begs Will to tell her about how he met her mom in the form of a bed-time story. Will decides to play along with Maya’s proposition, but also chooses to spice matters up by including in the tale all three of the women that he has had serious relationships with in the past. (He changes their names, of course, so that Maya won’t be able to tell which one is her mom until the conclusion of the story.) The women are Emily (Elizabeth Banks), Will’s high-school sweetheart who he had to part with when leaving their hometown to work for Bill Clinton’s 1992 presidential campaign in New York City; Summer (Rachel Weitz), Emily’s Manhattan-based, kinky old friend; and April (Isla Fisher), the resident copy-girl at the Clinton Camp.

     Definitely, Maybe comes across as being pleasant enough in its first act. As I mentioned before, the set-up proves intriguing, especially when one considers the fact that it belongs to the usually-blasé romantic-comedy genre. But as the story progresses, it becomes unexpectedly eerie. As Will tells his cute-as-a-button, barely double-digit-aged daughter about the nitty-gritty details of his love-life, the movie’s content becomes morally questionable. Isn’t there something inherently wrong with the idea of a grown man fondly reminiscing about his ex-lovers to a young girl? At one point in the movie, Will even slips and tells Maya that Summer admitted to once having lesbian group-sex with Emily, only to later raise her standards and begin fornicating with her much-older college thesis-adviser (Kevin Kline). To say the least, the exercise will leave any rational viewer who takes the narrative literally feeling a bit alienated.

     Sure, the performances in the movie are all likable. Reynolds reveals uncanny potential as a leading-man; he crafts a character that is thankfully far more relatable and affable than any real person who has ever worked for Bill Clinton could be. Breslin mainly just smiles and giggles in her part, but she retains every bit of the charm that she had in the lead-role in Little Miss Sunshine. Likewise, the three ladies in the movie (Banks, Weitz, and Fisher) all make for believable romantic-interests for Reynolds’ character. Still, the fact that Definitely, Maybe is as sympathetic a movie as it is makes it all the more disillusioning. I can’t imagine any thinking viewer not questioning the ethics of Will’s much-too-graphic confessions to Maya as they watch them unfold.

     Nevertheless, I can at least give the movie credit for being mildly interesting in the way that it thinks outside the box in presenting itself. Even when I was mildly offended by Definitely, Maybe, the movie always had me intrigued by the motions of its plot. For the sake of remaining optimistic about the state of mainstream cinema as whole, I’ll merely concede that the film is a failed exercise that may ultimately pave the way for equally clever, but more thoughtful entries in what many of us critics had previously written off as an insipid genre. As misguided as Definitely, Maybe is, it very well may represent a step in the right direction after all.

Definitely, Maybe is rated PG-13 and runs 111 minutes.

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