Definitely, Maybe Synopsis: A political consultant tries to explain his impending divorce and past relationships to his 11-year-old daughter.
Amid a relatively amicable divorce, a former political consultant, Will Hayes (Ryan Reynolds), agrees to tell his daughter Maya (Abigail Breslin) the truth about his past, his relationships, and how he met and fell in love with her mother. He changes the names of the three women with whom he had meaningful relationships, including his soon-to-be ex-wife, while Maya attempts to piece together the truth to discover which woman became her mother (whose real name is Sarah).
I remember enjoying this movie when it came out in theaters in 2008, and I’ve rewatched it several times. But this time around, I came to have more appreciation for it. The storytelling, the humor, and the cast were much better than I remember. Reynolds has perfected the art of sarcastic, dry wit over the past several years, but it’s so wonderfully subtle in Definitely, Maybe, rather than what we expect of him today.
Will is nothing more than a young man fresh out of college, trying to make his way in the world while making a difference, but finding frustration in the tediousness of moving his ‘way up the ladder.’ He’s relatable but also intelligent and handsome, which he has to be in order to charm three beautiful women over the next decade or so of his life. Will Hayes has an idyllic view of love thanks to his parent’s marriage, but that comes crashing down around him when his college sweetheart, Emily (Elizabeth Banks), turns down his proposal.
From that point on, the story kicks in as Will attempts to navigate his career while growing closer to his friend, April (a wonderfully quirky, energetic Isla Fisher), and dating and falling in love with Emily’s old college sorority sister, Summer (Rachel Weisz, who can do no wrong in any movie as far as I’m concerned!). The mystery of who Maya’s mother is hits a snag as Maya realizes it doesn’t matter who her mother is because she and Will are getting divorced anyway. Every single romance/would-be romance in Definitely, Maybe is a treat to watch, but the father-daughter relationship here brings the heavier emotion.
Divorce is difficult, not only for the two people splitting up but also for their children. You can see Maya’s desperate need to hear about how and why her father fell in love with her mother, as if telling the story would trigger those memories and feelings all over again. You see the hope on her face that her parents will somehow find that magic again and reunite.
But Maya is also pretty intelligent for an 11-year-old girl, and once she realizes the marriage is truly over, she focuses on helping Will find happiness again with someone else. I enjoyed these moments between Will and Maya during this rewatch because their relationship is truly the heart of the movie.
That being said, Weisz, Banks, and Fisher are all incredibly delightful. There is no wrong choice here, no woman who is so blatantly wrong for Will that you know he’s wasting his time. I could see Will ending up with any of them and would have been satisfied, although it’s pretty clear who he truly belongs with, even if he can’t see it until it’s too late.
The endings of Will’s relationships with these women are heartbreaking but never full of melodrama or tragedy. They’re believable, and you never feel any real hatred or resentment toward any of the characters. It’s something else that helps Definitely, Maybe stand out from some of the other movies in this genre. There’s no need to create a villain or push a one-dimensional woman or ex at Will to show us his true soulmate forcibly.
Definitely, Maybe is full of 90’s nostalgia, taking us back to the era before cell phones and email as Will worked for the 1992 Clinton campaign. He marvels at the rising price of cigarettes, becomes disenfranchised with politics as the Clinton-Lewinsky scandal breaks, and finds frustration in internet dial-up. Then there is the fashion and music, as campaign workers celebrate Clinton’s win in the presidential primaries with Vanessa Williams’s ‘Save the Best for Last’ and April introduces Will to Kurt Cobain and Nirvana.
There’s plenty to love about this movie, and you get the bonus of watching Kevin Kline as boozy, opinionated Hampton Roth, an author and professor dating Summer when she first meets Will. Really, it was difficult to find fault with anything in this movie. Perhaps the ending was tied up a bit too neatly? But it’s definitely perfect for the movie. Maybe. 🙂
Watched: 01/21/2019
Notable Song: Come As You Are by Nirvana







