The troubled loves of Definitely, Maybe

July 11, 2023

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, in order to soothe his pre-teen daughter Maya, 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, bourgeois-bohemian libertine wild child Summer, and Midwestern girl-next-door Emily - 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 it does not leave the viewer 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.

Should you watch Definitely, Maybe? Yes. It's enjoyable.

Also...

they should make a sequel set in present day.