Definitely, Maybe (2008)

Plot:

On the day she has her first sex ed class, 10-year-old Maya grills her divorcing dad Will Hayes about her conception. That night, he fills her in, changing the names of the women who were in his life then to keep her guessing which is her mom: Emily, his college girlfriend when he came to New York from Wisconsin for Clinton's '92 campaign; April, edgy, a little cynical, who misses her father; and, Summer, a writer attracted to older, established men. In demanding the story, Maya's motivation is clear: to get her dad to fall in love again with her mom. Will this parent trap work? In the telling, might Will discover his true Penelope? Definitely. Maybe.