
The synopsis above tells about what the movie is about. What it doesn't tell you is the wonderful wonderful story that it endeavours to tell over a bedtime story. It touches your heart, enlightens you about love in relationships... and more importantly.. that there's always hope that you'll find that ideal person someday.
The story of finding out of the 3 people in Will's life that he has ever loved, one of them happens to be his daughter, Maya's mother. The story is intrinsically woven, so much so that you think it's going to be another of those predictable love stories... you know? But the way the director throws a curveball at you is very smooth and unexpected. The three women in his life are as follows:

Along the story, each of these women create a niche for themselves, portraying themselves in a different identity of modern women. Those who take life with a pinch of salt like April, those that are more conservative and careful like Emily, or those who are the go-getters and take life as it comes like Summer. Which of these is Maya's mom... and the underlying question of it all is... who of these three does Will truly love?
I'm not going to spoil the ending for you, but I have to admit that this movie kind of challenged certain perspectives that I had, especially with regards to stereotypes. In one simple movie.. you see unconditional love, you see unrequited love, you see love that transcends, you see love that understands. Of course, you also see the other side of love.. the selfish love, the deluded love and the love that doesn't let go when it is time.
Even as I'm typing this, I find myself wondering exactly what love is it that is prevalent in society these days... and how wonderful it is that despite the seemingly loss of importance of the sanctity of true love, it is still there in the obscurity of a seemingly feeling-less Earth. Because there's always hope. In that hope... there lies the promise, though it may be thin, of eternal bliss in a marriage or a relationship. It's definitely possible.
The linguistic puns in this movie are great. I love how "Definitely Maybe" has different connotation in the movie. How two of the three girls are "Definitely Maybe" candidates for Will. How Will himself is a "Definitely Maybe" kinda guy. Or how commitment to some people is "Definitely Maybe"... there're a lot of different ways to look at the movie and how the title plays around it, but it's definitely worth an analysis. =)
In short... love is definitely something... I wonder if it'll ever happen to me. =)