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The next day while hitch-hiking down the road, Anna and Declan are caught in a hail-storm and take shelter in a nearby church, where a wedding is taking place. That night, they sleep in the same bed, but do not admit their new feelings for each other. This stirs feelings that neither had expected. During dinner, when other couples kiss to show their love for each other, Anna and Declan are "forced" to kiss as well. That night, Anna and Declan are forced to stay at a local bed & breakfast in Tipperary, where they pretend to be married, taking the name "O'Brady-Callaghan" so that their conservative hosts will allow them to stay. During the story, they lose track of time and miss the train. So the woman gave her wedding guests a sleeping potion so she could run away with a young Celtic warrior she did love. In doing so, Declan also tells Anna of an old Irish legend about a young woman engaged to an elderly lord that she did not love. They ask each other what they would grab if their homes were on fire and they had only 60 seconds to flee. While waiting, they hike up a hill to the ruins of a nearby castle. Anna and Declan reach a railway station and decide to wait for the next train. Anna and Declan are ejected from the pub by the owner for fighting on the premises. Declan fights them, displaying unexpected strength for a man of his size, and retrieves Anna's bag. Anna and Declan eventually make their way on foot to a roadside pub, where they discover the three van thieves going through Anna's luggage. Before she can enter the van, they drive off without her. Ignoring Declan's warning, Anna accepts the ride and hands them her luggage.

Continuing on foot, Anna flags down a van with three travellers who offer her a lift. Anna steps in cow-dung while attempting to move the animals, and tries to clean her expensive shoes while leaning on Declan's car which causes it to roll downhill into a stream. Their travel is interrupted by a herd of cows blocking the road. He also mocks her belief in a leap year "tradition" of women proposing to men.

Along the way, he makes fun of her fancy Louis Vuitton luggage, which he calls "Louie". At first he refuses, but after his tavern is threatened with foreclosure, he agrees to drive her for EUR500. She requests him to taxi her across the country to Dublin. Anna tries to enlist the help of Declan O'Callaghan, the surly Irish innkeeper. The severity of the storm, however, forces her to be put ashore at a small seaside village called Dingle, where she makes her way to a local tavern. During the flight, a storm diverts the plane to Wales, where Anna hires a boat to take her to Cork. Anna wishes to invoke an Irish tradition that a man who is proposed to on leap day must accept the proposal. She decides to travel from Boston to Dublin, to propose to him on February 29, leap day, while he is there at a conference.

Successful real estate agent Anna Brady is frustrated that her cardiologist boyfriend Jeremy Sloane still has not proposed to her after four years.

The synopsis below may give away important plot points. 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. 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. for a price the agreed-upon fare would cover much of his debt, which would allow him to keep the pub/inn. Despite their antagonistic meeting, struggling pub/innkeeper Declan O'Callaghan agrees to drive Anna to Dublin. She gets stranded in Dingle, her unintended entry into Ireland, a few days before Leap Day. But her trek from Boston to Dublin is anything but smooth. 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. 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. Jeremy Sloane, has not yet proposed to her after four years of dating. One of the few things she has not been able to control is getting married her boyfriend, cardiologist Dr. Busy as she is as a Boston stager, Anna Brady likes to control all aspects of her life.