Definitely, Maybe (2008)

Definitely, Maybe plays like a film that's in the middle of being rewritten. You get the sense that there was an original version of the script, someone recommended a structural change, and the writer started to implement it, then time ran out and they just filmed what they had. It's messy.

The film's only saving grace is Ryan Reynolds, who is supremely watchable in just about anything. Which doesn't say much for Definitely, Maybe; Ryan Reynolds would probably be more entertaining if he were reading out a phone book than starring in this. Sadly, the DVD of Reynolds' rendition of The Yellow Pages hasn't been released yet, so Definitely, Maybe will have to do. Reynolds plays Will Hayes, a political consultant whose life didn't quite go the way he'd planned - he's getting divorced, and he isn't the president yet. Hoping to gain some insight into why her parents are splitting up, his 11-year-old daughter asks Will to tell her the story of how he met her mother, which launches him into a very, very long account of every relationship he's ever had. Including lots of intimate details and incriminating anecdotes of the kind you really would never tell a small child, particularly if they were your own offspring.

Essentially, then, we get to watch each of Will's relationships blossom and then fall apart, interspersed with brief moments of Will tucking his daughter into bed, making her a hot chocolate, or awkwardly answering her questions about what exactly a "threesome" might be. That's the main problem with the film, right there: it just doesn't make sense. The idea of a father explaining to his child how he fell in love with her mother and, in the process, gaining his own insight into what went wrong with his relationships and how to put them right could potentially work; playing around with subjectivity and the idea of the unreliable narrator shouldn't be too much of a stretch, either. But Definitely, Maybe is too stupid to play it off like that. Instead, Will apparently recounts every single thing that happened - every awkward bit of flirting, every alcoholic drink consumed and illicit cigarette smoked, and every tiny tiny detail of everyone's mannerisms and speech patterns. (Including every time his so-called friends make jokes about suicide whenever anything bad happens to him - hilarious, guys! Or, you know, really really fucking inconsiderate.)

As an added bonus, we get to watch as a young Will gradually becomes more and more disenchanted with politics, eventually abandoning his dream of becoming the President of the United States as he's disappointed with Bill Clinton, to the point where he calls his earlier ambitions stupid. But that's not the story he's supposed to be telling; it just doesn't make sense. What seems more likely is that the film was originally supposed to be just a straight account of Will's life and relationships, but somewhere along the line someone suggested having it be a story he's telling his child - but no-one saw fit to rewrite any of it. It's awkward. And it doesn't help that actually it's all quite boring; Will's daughter tells him off a couple of times for being a "slut", but in reality he's had two relationships with women, both of whom he's proposed to, and fallen in love with his best friend along the way. That makes the term "slut" not only offensive and outdated but also kind of nonsensical - are we just supposed to go "ah, kids - what do they know?" and laugh here, or what?

To add insult to injury, Definitely, Maybe isn't even a comedy, because it's not funny. With a less charismatic actor in the leading role, it would be virtually impossible to even get through to the end of this film; as it is, well, Reynolds deserves better.

IMDB link