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.