The troubled loves of Definitely, Maybe
July 11, 2023 (several additions made throughout February - April, 2025)
Rating: 4/5
Definitely, Maybe is a 2008 romance period movie shot at the end of said period (the Bush-Clinton-Bush era). It's about the consequences of words and actions, and about committing to people, not just ideas about people.
The story is told by the protagonist, Will Hayes (played by Ryan Reynolds), in order to soothe his pre-teen daughter Maya (Abigail Breslin), who's riled up after a sex ed class. The story is about how Will met Maya's mother.
The journey spans many years and three women - aimless party girl April Hoffman (Isla Fisher), bourgeois-bohemian libertine wild child Summer Hartley (Rachel Weisz), and Midwestern girl-next-door Emily Jones (Elizabeth Banks) - who bounce in and out of Will's life. Every time one of them appears to come close to him circumstances conspire against any lasting bond forming.
The four characters change over the course of the movie. The young, idealistic, confident, and ambitious Will is hardened and wiser. April evolves from a self-proclaimed "nothing" to someone with her own office at Amnesty International. Summer becomes a mom. Emily has the least of a trajectory, but one can say that if nothing else she definitively stops relying on Will to bring her contentment.
It is a more interesting movie than one might expect.
My late wife liked the movie a lot as it captures the sense of excitement and hope that the Bill Clinton campaign for president generated among young people in the early 1990's. It also captures the painful disappointment and growing disillusionment that the actual Clinton presidency brought with it. The movie was in a sense 90's nostalgia before 90's nostalgia was a thing.
Definitely, Maybe is also well structured. Every scene moves the viewer closer to the climactic reveal of who Maya's mother is. Every conversation contains tension as the characters try to achieve personal or professional objectives.
It's an unusual romance movie in that it does not leave viewers with much certainty that it is a lastingly happy ending. April's history with men and Will's with relationships do not inspire confidence.
A common viewer comment is that Will was wrong to marry Emily after she cheated on him. True, but Will also held on to a book for eight years that was very important to April. His stated rationale for doing so is that it was the only thing he had left of April - while he was married to Emily.
April is an interesting character who has clear similarities with the female protagonist, Tom, in the movie The Only One. But Tom and April ultimately choose different paths.
Definitely, Maybe was written and directed by Canadian Adam Brooks. In interviews he has talked about what inspired him to make the movie and why he structured it the way he did:
Should you watch Definitely, Maybe? Yes. It's enjoyable.
Also...
they should make a sequel set in present day.
Who does Will end up with?
Will ends up with April, the woman he first met at a Bill Clinton campaign office in New York City in 1992. At the time, he was in a relationship with Emily, to whom he was planning on proposing.
April's relationship with Will during that time is a critical part of the movie and of the trajectory for Will, April, and their relationship. During that time April saw the naive earnest Will.
April saw a Will so charming and earnest that she was a split second from accepting when he told her the proposal he was planning for Emily. The same earnest attitude he had displayed when they first met and he vainly tried to convince her to support Clinton.
Contrast that earnestness to his drunken insistence that he loves April after his professional and personal lives had fallen apart after and because of his relationship with Summer.
Given that April had seen Will's heartfelt eloquence when talking about Emily, it's hardly surprising she was offended by his clumsy, drunken, and borderline desperate attempt to proclaim his love to April.
But April was already in love with Will, probably had been from the moment they were smoking cigarettes outside a convenience store the second time they met in the movie, although it took her a while to accept it.
Why was April so upset that Will had held onto the copy of Jane Eyre?
Towards the end of the movie, after having signed his divorce from Emily, Will visits April at her office to give her the copy of Jane Eyre that her dad had bought and inscribed for her when she was a child.
The book is an important subplot in the movie and a metaphor for how April is searching for something that is missing in her life. Similarly, "something always seemed to be missing with Kevin" (her last boyfriend in the movie) as she tells Will just before he gives her the book.
After giving her the book Will admits to having had it for years, prompting April to ask him to leave.
Why did April ask Will to leave when he gave her the book?
Because Will had betrayed her. He knew how important the book was to her He knew she was looking for the book in second-hand and antique bookstores while he was sitting on it.
Why did April forgive Will?
April forgave Will because she loved him, as she had for a long time, and she finally believed that he loved her.
Who is the mom in Definitely, Maybe?
Emily is the mother of Will's daughter. Emily's real name is Sarah, but Will changed her name in the story to make it less obvious which one of the women is the mother.
What is Definitely, Maybe really about?
While Definitely, Maybe tells the story of how Will met Maya's mother, the movie is really about youthful idealism giving way to mature realism.
Idealism vs Realism
Will Hayes's journey from naive idealism to seasoned realism is really what the movie is about. In the beinning of the story Will is a young man, fresh out of college, whose ambition is to become President of the United States.
His immediate objective is to help make Bill Clinton president. Former president Clinton is a perfect symbol for the idealist to realist journey, as he inspired a generation to rally to him, only to get bogged down in messy personal affairs (Emily cheating on Will mirrors Bill cheating on Hillary).
While trying to fundraise for the campaign Will learns that truth or reason are not as important as the story he tells the party supporters he calls to sell seats and tables to a fundraiser.
He is also slowly corrupted by Summer, an ambitious young woman who has no issue with sleeping her way up the ladder even if it means hurting those she claims to care about.
This comes to a head when Summer, at the behest of her professor, lover, and mentor Hampton Roth (played by Kevin Kline), writes a magazine article on the mayoral candidate Will works for while Will is about to propose to her. Will's client is not the stand-up guy he poses as and Summer has no problem putting her own needs and desires above Will's success.
The fallout from the article tanks Will's consultancy and torpedoes his personal life, setting up the scene where he drunkenly tells April he loves her.
Searching for what's missing
April leads a life trying to find some missing piece.
She misses her dead who passed away when she was a teenager.
She misses the book her dad inscribed for her that was lost during a move.
Her (offscreen) boyfriend is missing on her birthday because he has a gig out of town.
She finds something is missing in her (offscreen) other boyfriend Paco.
She finds something missing in Will when he drunkenly states his love to her.
She ultimately finds something missing in her longtime boyfriend Kevin.
What was missing?
April likely missed her dad and the qualities he possessed and embodied. It's reasonable to assume he was learned, thoughtful, and caring. He was probably not beholden to the whims of pop culture.
Will certainly caught April's attention by casually admitting he had no idea who Curt Cobain is.
In spite of her bargain-bin anti-marriage speech she's deeply affected by Will's rehearsal proposal.
Will's experience as writer and especially writer made an impression on her, as demonstrated by her returning to New York City to get together with after months of letter writing between the two (mostly dealt with in a voiceover on a brief montage), only to find out that Will was about to propose to Summer.