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A father in the midst of a divorce is pressured by his 10-year-old daughter to reveal the story of how he met her mother. He reluctantly agrees, but changes the names and some details to make it a guessing game for his daughter. As he recounts his past romantic entanglements, he realizes that a second look at his past might give him a second chance at his future.
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Some movies that have similar genres and were produced around the same time as Definitely, Maybe include The Invention of Lying, Raising Helen, No Reservations, New York, I Love You, She's Out of My League, Good Luck Chuck.