As far as RomComs go, my favorite is "When Harry Met Sally". There have been many before and many since, but none of them really come close to the humor and real life awesomeness of this genre defining classic. "Definitely, Maybe" tries really hard to be sophisticated and fresh, but ultimately falls a little short of wholly satisfying.
Ryan Reynolds plays William Hayes, an idealist who has aspirations one day to become president of the U.S. Fast forward to the future and he has a daughter who wants him to tell her the story of how he met mommy and fell in love. So he decides to tell a story with fabricated names so she will have to guess which one of the three people in his life at the time was her mommy. A simple premise that is fairly poorly worded and convoluted in the movie. This is the film's biggest downfall. RomComs should have a lightness to them. Not that they can't be deep, but they shouldn't be structured so that they are clunky. This film feels way too long. Unfortunately, it kind of needs to be. So it could have used a bit more snappy writing. And also a bit of focus. You end up learning very little about these characters in the large amount of time they spend onscreen. I enjoyed all of the characters, I just wish I knew a little bit more about most of them.
Reynolds does a great job trying to liven the mood in almost every scene. I do enjoy his comedic timing. He is very charming and charismatic. You really don't have to bend reality to understand why he could get three different women to like him. The women are also well suited for their parts. Rachel Weisz is a happy surprise and a fun, flirty writer named Summer who is dating Kevin Kline when Will and Summer first meet. The scenes between these two/three are some of the best scenes in the movie. Elizabeth Banks plays a part that is way smaller than it should have been. Lastly, Isla Fisher shows why she almost became popular. If only Amy Adams hadn't blown up. She IS charming, but her character seems forcibly quirky. All of the actors in this film do their best with what they have to work with. I enjoyed all the characters, just not as much as I should have.
Script issues aside, this movie does have some charm to it. Abigail Breslin has a small but cute part as the daughter to which Will tells his story. Their scenes are really quite adorable. Even the film's story overall is nice and sweet. I just wish that it didn't feel like work to watch it.
6 out of 10 stars