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Definitely, Maybe

Definitely, Maybe

Three relationships. Three disasters. One last chance.

20086.91h 52m

Overview

When Will decides to tell his daughter the story of how he met her mother, he discovers that a second look at the past might also give him a second chance at the future.

Directed by Adam Brooks
Written by Adam Brooks
Produced by Eric Fellner, Tim Bevan
Box Office0Revenue: $55.4M

Top Cast

Ryan Reynolds

Ryan Reynolds

Will Hayes

Abigail Breslin

Abigail Breslin

Maya Hayes

Elizabeth Banks

Elizabeth Banks

Emily

Isla Fisher

Isla Fisher

April

Rachel Weisz

Rachel Weisz

Summer Hartley

Kevin Kline

Kevin Kline

Hampton Roth

Derek Luke

Derek Luke

Russell McCormack

Liane Balaban

Liane Balaban

Kelly

Annie Parisse

Annie Parisse

Anne

Nestor Serrano

Nestor Serrano

Arthur

Themes & Keywords

love of one's lifeparent child relationshipelection campaignpoliticsnarrationmarriagemake a matchsex educationromancebest friendfalling in loveprecocious childdating woeslove problemspast relationshipyoung daughterpast lovefather daughter relationshiprelationshipsdating historyimpending divorcepolitical ambition

About Definitely, Maybe

Definitely, Maybe is a comedy, romance film released in 2008 exploring themes of love of one's life, parent child relationship, election campaign, politics, narration, marriage. Directed by Adam Brooks, it stars Ryan Reynolds, Abigail Breslin, Elizabeth Banks. When Will decides to tell his daughter the story of how he met her mother, he discovers that a second look at the past might also give him a second chance at the future.

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