Much as she has to do 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 as her boyfriend, cardiologist Dr. Jeremy Sloane, has not yet proposed to her after four years of dating, marriage to Jeremy what she wants. 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. Regardless, Anna, despite hating surprises, decides to surprise Jeremy by showing up in Dublin where he is attending a conference and proposing to him on leap day. But Anna's trek from Boston to Dublin is anything but smooth. Anna gets stranded in Dingle, what ends up being her unexpected point of entry in Ireland, a few days before leap day. Despite their antagonistic meeting, struggling pub and innkeeper Declan O'Callaghan agrees to drive Anna to Dublin... for a price, as the agreed to 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 into Dublin by February 29 and her planned romantic fairytale proposal. Through their time together, Anna and Declan may find that there are more important things in life to them than having that fairytale February 29 proposal and saving the pub/inn through extortion of Anna respectively.