Anna Brady is a successful Boston real estate stager who has been dating her cardiologist boyfriend, Jeremy, for four years. When Jeremy travels to Dublin for a conference, Anna learns about an Irish tradition that allows a woman to propose to a man on Leap Day. Seizing this opportunity, Anna decides to fly to Dublin and propose to Jeremy herself. However, her travel plans go awry due to bad weather, and she ends up stranded in the small village of Dingle. Desperate to reach Dublin on time, she enlists the help of Declan O'Callaghan, a surly innkeeper with his own set of troubles.

As they journey across the beautiful, but unpredictable Irish countryside, Anna and Declan encounter various obstacles that compel them to rely on each other. Along the way, Anna's meticulous and controlling nature clashes with Declan's laid-back attitude. Despite their initial animosity, moments of vulnerability and shared experiences start to soften their interactions. As they draw closer to their destination, Anna begins to question her intentions and reevaluate what she truly wants in life.