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A surprisingly charming romantic comedy from director Adam Brooks that thankfully doesn’t choke you to death with the sweetness.

In the midst of a separation and divorce from his wife, Will (Ryan Reynolds) still has regular visits with his daughter Maya (Abigail Breslin) to look forward to, but a surprise sex education class at her school prompts some uncomfortable questions.  This talk leads into a discussion of him and her mother’s relationship, made especially awkward considering the fact that it’s in the process of ending.

Will agrees to relate the story to her, but only if he can change the names of the three women he was involved with at varying times to keep her from changing how she might feel about her mother or him based on their past indiscretions or foibles.  Definitely, Maybe is set across a period from 1992 to 1997, and begins as he leaves his college sweetheart Emily (Elizabeth Banks) behind in Madison Wisconsin to travel to New York City and work on the Clinton Presidential campaign.  While working there as a volunteer, he meets April (Isla Fisher), who seems to be involved for more mercenary reasons as a paid employee.  They have a friendly bickering banter between them, and the final candidate who may be Maya’s mom is introduced when Will delivers a package to a friend of Emily’s from college.  The item turns out to be Summer’s (Rachel Weisz) diary, and he sneaks a peek and finds indications that Emily and Summer may’ve been more than friends in college.

Summer is flirtatious with Will, in spite of being in a relationship with an older man, but Will resists.  He’s promoted at the campaign office, and ends up spending April’s birthday with her; they seem to be getting closer to a romance.  Emily arrives for a visit and Will is on the verge of proposing to her when she reveals that she slept with his roommate back in Wisconsin, effectively ending the relationship.

Skipping forward a few years, Will runs into Summer at a reading by her boyfriend, who has now split with her.  Will and summer begin dating as Will maintains a pen-pal relationship with April, and when she returns suddenly, pretty obviously to declare her love for him, he’s in the process of buying an engagement ring to give to Summer.

April splits again, obviously hurt, and Summer is goaded into writing a scathing article about a candidate Will is working with, which effectively ends their relationship, but none of these women seem to stay out of Will’s life for long.

The film successfully manages to conjure the bygone days of the 90’s very well, reflecting the styles and fads in amusing detail, and the leads are all charming even as you know that something obviously goes wrong somewhere down the line.  The only thing I found a little groan worthy was something I felt was cribbed from Serendipity, but I won’t mention it here so as not to spoil anything, but if you’ve seen that film, it’ll become apparent as you get further into this one.

Definitely, Maybe comes to DVD with features that include an entertaining commentary from writer/director Adam Brooks and Reynolds himself, a small selection of deleted scenes, a featurette on the making of the film called Creating A Romance, and a short feature called The Changing Times Of Definitely, Maybe in which they go over the details of showing the subtle changes in fashion and accessories in the film.  A handful of trailers are also included to round out the disc.

A sweet and funny film, this is a great date movie and worth a look to most anyone who wants to have a laugh and maybe end up saying “Aww” by the time credits roll.

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