Definitely, Maybe is the story of Will Hayes (Ryan Reynolds), whose 10-year-old daughter Maya (Abigail Breslin) wants to know how he met her mother, who he is currently undergoing a divorce with. Will decides to tell her the whole story, but changes the names of the women who came and went through his life, leaving Maya to guess who her mother is. The stories he tells are shown in long flashbacks, starting with when he leaves his home of Wisconsin and his college sweetheart Emily (Elizabeth Banks) to work on the Clinton campaign. There, he meets aspiring journalist Summer Hartley (Rachel Weisz) and copy girl and close friend April (Isla Fisher). He decides to propose to Emily, and he practices on April, who realizes she has feelings for him but keeps them to himself. Emily confesses that she has been unfaithful, purposely distancing herself from Will. Summer and Will become involved after she breaks up with the older writer she was seeing, but before he pops the question, she writes an article betraying Will and getting him fired. His friend April reconnects with Will, and he realizes that he has feelings for her, but his confession escalates into a fight, and by the time he is ready to reconcile, she is living with her boyfriend. Maya correctly guesses who her mother is, but the subtext of her plan, to get her dad to fall back in love with her mom, doesn't work, nor does she want it to any longer. Instead, she encourages him to go back to his true love and assures him that it's never too late for a second- or third, or fourth- chance.