Anna (AMY ADAMS) is a Boston-based career woman who has dated cardiologist Jeremy (ADAM SCOTT) for nearly four years. Anna is ready to take the relationship to the next level and get married. Jeremy, though, doesn't seem to have any interest in making such a long-term commitment. Instead, he goes on an extended business trip to Ireland.
Sad and depressed, Anna surfs the Web one night and comes up with the perfect solution. She will fly over to Dublin and surprise Jeremy on Feb. 29th, a date that happens every four years that many Europeans treat as a day in which it's socially acceptable for the woman to ask the man for his hand in marriage.
One problem: a fierce storm has forced Anna's plane to land on the other side of the country. She hooks up with Declan (MATTHEW GOODE), a hunky tavern owner who needs cash quick to keep the lenders at bay. He consequently decides to drive her to Dublin himself for a fee. Amid much bickering, the two fall in love.
What follows is a road comedy in which this mismatched, oil-and-water pair become kindred spirits. At the end of the road, though, is Jeremy and Anna's feelings for him.