Anna Brady (Amy Adama) from Boston is a planner who stages apartments for Realtors. Anna has been dating cardiologist, Jeremy (Adam Scott) for four years and they are buying a high standard apartment in Davenport together. Anna expects Jeremy to propose to her on a dinner date but he gives her a gift instead, after which he travels to Dublin for his work. Anna thinks he is the one for her and decides to take matters into her own hands. Anna decides to meet him in Dublin on the February 29th and propose to him in accordance with an old Irish folklore tradition from the Fifth Century of leap-year proposals by women where the man has no other choice but to accept the woman's proposal. However, her airplane is forced to land in Wales due to bad weather and she is not able to find a connection since the Dublin airport is closed. She decides to travel on a small boat but is forced to disembark in Dingle due to a storm. Anna walks to the only restaurant and inn and hires the unfriendly owner Declan (Matthew Goode) to drive her to Dublin. Declan agrees to drive her as he needs the money to pay off his debts and save his inn. They go on an adventure together which will make a lasting impression on both of them. In the end, she rejects Jeremy's faux proposal and goes back Declan who gave her the best moments in her life.