movies
Movies like Definitely, Maybe
Definitely, Maybe
2008
4.4/5
Romantic comedy: Will Hayes, a 30-something Manhattan dad is in the midst of a divorce when his 10 year old daughter, Maya, starts to question him about his life before marriage. Maya wants to know absolutely everything about how her parents met and fell in love. Will's story begins in 1992, as a young, starry-eyed aspiring politician who moves to New York from Wisconsin in order to work on the Clinton campaign. For Maya, Will relives his past as a idealistic young man learning the ins and outs of big city politics, and recounts the history of his romantic relationships with three very different women. On the campaign, Will's best buddy is Russell McCormack. They not only have similar political aspirations, they share the same type of girl problems, too. Will hopelessly attempts a "PG" version of his story for his daughter ad changes the names so Maya has to guess who he finally married. Is her mother Will's college sweetheart, the dependable girl next-door Emily? Is she his longtime best friend and confidante, the apolitical April? Or is she the free-spirited but ambitious journalist? As Maya puts together the pieces of her dad's romantic puzzle, she begins to understand that love is not so simple or easy. And as Will tells her his tale, Maya helps him to understand that it's definitely never too late to go back...and maybe even possible to find a happy ending.

Filter by:
Cross-category suggestions
Filter by:
Filter by:
Filter by:
Filter by:
Filter by:
Filter by:
Filter by:
Filter by:
Lists with Definitely, Maybe



- 38 Movies
watching
List includes: Bride Wars, Penelope, What Happens in Vegas
a few months ago
0
@Sallymaa



- 38 Movies
Romance Movies
List includes: 27 Dresses, The Proposal, 10 Things I Hate About You
July 2025
1
L
@liam-fryer



- 5 Movies
sarah
List includes: The Holiday, About a Boy, Love Actually
June 2025
0
S
@smeeagain



- 4 Movies
movies to watch
List includes: He's Just Not That Into You, The Sisterhood of the Traveling Pants, Definitely, Maybe
May 2025
0
G
@gabby-marazzi



- 66 Movies
seen
List includes: 500 Days of Summer, 27 Dresses, She's the Man
March 2025
0
A
@ana-chukhrukidze

- 1 Movie
Watchlist
List includes: Definitely, Maybe
January 2025
0
@KevinS


- 2 Movies
Romance
List includes: About a Boy, Definitely, Maybe
January 2025
0
E
@ella-mathews



- 30 Movies
great rom-coms
List includes: 27 Dresses, She's the Man, The Proposal
November 2024
0
@ipluggedin



- 37 Movies
- 1 Show
To watch
List includes: The Proposal, How to Lose a Guy in 10 Days, What Happens in Vegas
November 2024
0
@sarah-partington



- 143 Movies
- 7 Shows
watched
List includes: She's the Man, The Proposal, Hellboy
September 2024
0
E
@enrique6374



- 78 Movies
Watchlist
List includes: 27 Dresses, The Proposal, 10 Things I Hate About You
July 2024
0
@livv



- 210 Movies
Seen
List includes: 500 Days of Summer, Alice in Wonderland, Harry Potter and the Prisoner of Azkaban
May 2024
0
E
@elizabetta