Adam Brooks’ Definitely, Maybe is the kind of fairytale that could only possibly work in today’s post-millennium, cynical times.

Will Hayes (Ryan Reynolds) is a sweet, slightly overly dramatic speechwriter and divorced dad to Maya (Abigail Breslin). The film opens with his voice-over, right away setting up that this is not your typical romantic comedy. After picking up his daughter from school and learning her class got a lesson in sexual education that day, Will discovers Maya’s hell-bent on finding out how her father came to fall in love with her mother, a topic all the more heated now that they are no longer together. Will starts his story way back in the early ’90s, preparing his daughter to hear about the three women he had serious relationships with and leaving it up to her to figure out which one is her mother. Though it is painfully obvious which woman is in fact Maya’s mother from the moment audiences meet all three, Definitely, Maybe is just as sweet (and, at times, just as slightly overly dramatic) as its protagonist, offering reminiscence of some simpler times to cushion the harsh blow of the ever-changing world around both father and daughter.

Definitely, Maybe is in many ways a love letter: not only to the women Will has left (or who left Will) but also to the city that surrounds him, New York. Brooks, along with his cinematographer, Florian Ballhaus, are fond of long tracking shots of the characters moving through the city streets, lingering on the architecture, foliage and background players to exhibit that it is all important to this man’s story. The city is as much involved as any of the women; in fact, it could be considered Will’s fourth love. It is the kind of New York that only exists in movies, from the pleasing fall color palette to how Will manages to cross paths time and again with the same people, giving it an almost magical, ethereal quality and undoubtedly being used as a device to further drive home Brooks’ modern-day fairytale imagery.

Unfortunately, much of Definitely, Maybe’s dialogue feels contrived, and the only reason the movie is saved is because of its phenomenal casting. Elizabeth Banks as Emily, Will’s college girlfriend, perhaps has the worst lines, but her down-to-earth and sunny demeanor delivers the words at times a bit sheepish but never cartoonish. Rachel Weisz as Summer, the free-spirited, precocious writer, makes herself a bit more mysterious, and in turn creates another dimension to her character just through subtle eyework and body language while interacting with Reynolds. Isla Fisher as April, the somewhat flakey but always hopeful doe-eyed ingénue, easily flits back and forth between serious and goofy, warming the audience to her immediately. Since the just-under-two-hour course of Definitely, Maybe must include the arc of all three relationships, some are better developed than others, which only makes it all the easier to determine just exactly how the story will end. Ironically, though the audience is often one step ahead of Will (and therefore one step ahead of the film itself), there is never a dull moment; anticipation runs high as viewers find themselves easily caught up in this messy world, rooting for the young man to finally come to his senses both in the past and the present.

Since the story is mostly Will’s, Reynolds is really given a chance to shine as a leading man, for the first time in a non-genre feature film. He eagerly accepts the challenge and gives every scene his all, making his performance the biggest joy to watch.

Unfortunately, Will’s love life is just so complicated that it takes the majority of the movie to explain, relegating Breslin to a supporting player. She doesn’t get to offer much more than some spunky retorts and overly enthusiastic voice-over. The few scenes she shares with Reynolds she of course steals, though for the most part, those are moments already seen just by viewing Maybe’s trailer. What is nice, though, is how Breslin manages to pop up right before audiences have completely forgotten she is the reason for this diatribe, which leaves the impression that throughout everything, she is always on her father’s mind. If nothing else, that is a sweet sentiment with which to be left.

For some reason, watching Definitely, Maybe in anamorphic widescreen on the DVD (Universal Studios Home Entertainment, MSRP: $29.98) makes the images look compressed, as if the original was just over 2.35:1 and therefore had to be refigured for at-home systems. The result is not completely distracting, but to a trained eye, it is noticeable. However, the rest of the DVD offers features great enough to make up for any visual quality shortcomings.

The audio commentary with Brooks and Reynolds sounds like two buddies hanging out and having a good time, which is welcoming, though not necessarily insightful. There are also the obligatory deleted scenes, as well as two featurettes, “Creating a Romance” and “The Changing Times of Definitely, Maybe,” both of which are exactly what they sound like.

“Creating a Romance” is a behind-the-scenes look at the storytelling devices used to set apart Will’s three relationships. Through interviews, the audience is given a little backstory on each love interest, explaining just how she is different from the next.

In “The Changing Times of Definitely, Maybe,” viewers are taken behind the scenes of the production design and given a crash course in how the crew transformed Will’s world through the decades. This is a chuckle-worthy piece, mostly because of the nostalgia it invokes, especially when considering the music choices within the film.

A gag reel would have been a nice inclusion as well, but regardless, at-home audiences should not take an indecisive cue from Definitely, Maybe’s title and debate with themselves whether or not to pick this one up on DVD; the verdict should definitely lean toward the former.

Definitely, Maybe is now available on DVD.