In the midst of a rather 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 with, 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 Definitely, Maybe when it came out in theaters back in 2008 and I’ve rewatched it several times since. But this time around, I came to have a bigger 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 being more or less over the top, which is what we expect of him today.
Will is really 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 he’s 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 parents’ 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 really 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 is Maya’s mother hits a snag as an emotional 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 it’s the father-daughter relationship here that brings the heavier emotion.
Divorce is difficult, not only for the two people splitting up but for their children as well. 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 will somehow trigger those memories and feelings all over again. You see the hope in her face that her parents will somehow find that lost magic 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. It’s these moments between Will and Maya that I really enjoyed 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 just 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 all heartbreaking, but they’re 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-lover at Will to forcibly show us his true soulmate.
Definitely, Maybe is full of 90’s nostalgia, taking us back to the era before cell phones and email as Will works 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. And then there is the fashion and the 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 added bonus of watching Kevin Kline as boozy, opinionated Hampton Roth, an author, and professor who is 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.