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Busy as she is as a Boston stager, Anna Brady likes to control all aspects of her life. One of the few things she has not been able to control is getting married; her boyfriend, cardiologist Dr. Jeremy Sloane, has not yet proposed to her after four years of dating. She hates the story told often to her by her father Jack Brady that there is an Irish tradition that allows women to propose to their loved one on February 29, which is what purportedly got her paternal grandparents together. Anna hates surprise herself, but she decides to surprise Jeremy by showing up in Dublin, where he is attending a conference, and proposing to him on Leap Day. But her trek from Boston to Dublin is anything but smooth. She gets stranded in Dingle, her unintended entry into Ireland, a few days before Leap Day. Despite their antagonistic meeting, struggling pub/innkeeper Declan O'Callaghan agrees to drive Anna to Dublin... for a price; the agreed-upon fare would cover much of his debt, which would allow him to keep the pub/inn. Largely because of their antagonism, Anna, Declan and their third, Louis (what Declan calls her Louis Vuitton suitcase), get into one misadventure after another, which threatens Anna's arrival to Dublin by February 29. Through their time together, Anna and Declan might find that there are more important things in life than having that fairytale February 29 proposal and saving the pub/inn through extortion of Anna.