While Anna Brady (Amy Adams) fixes apartments in Boston, making them more appealing to buyers and renters she learns her lover Jeremy (Adam Scott), a special young doctor, has taken a trip to the jewelry store and expects a diamond ring for a nightcap after dinner. When it becomes ear-rings she decided to evoke an old tradition, on February 29th a woman can propose to her man.
In her drive to make this obvious perfect coupling she follows Jeremy to Ireland to ask for his hand in marriage. At that point she becomes Daisy Mae Scroggs from Li'l Abner as she drives toward "Sadie Hawkins Day" - the day in Dogpatch on which all bachelors run from clutching women who want to marry. That day is February 29, Leap Year. She is cursed on her trip like John Candy and Steve Martin in Planes, Trains and Automobiles - every barrier comes up to slow her down.
Walking in heals on a muddy landscape and following a bar fight she sets out on a road trip with Declan (Matthew Goode) who she hires to get her to Jeremy. From pushing his car off an edge to sleeping in the shower they share mud and a few days together.
But in a back-to-the-50's style, one kiss and her heart skips a beat and the equation of perfection is in trouble. A song about sweet dreams puts them in the mood for love and they attend a Catholic Wedding on Sunday, and we all know all her inhibitions and ambitions are about to end.
Amy Adams is appealing even in the limited script but Leap Year, doesn't leap, jump, or rise to a sufficient level to get it out of the mud.