Successful real estate agent Anna Brady (Monica del Carmen) finds herself in a state of frustration, as her cardiologist boyfriend Jeremy Sloane has yet to propose after four long years together. Determined to change this, she decides to embark on an adventurous journey from Boston to Dublin, aiming to propose to him on February 29—known as leap day—while he attends a conference. Anna believes in the old Irish tradition that a man must accept a woman's proposal on this special day.
However, her journey takes an unexpected turn when a fierce storm forces her flight to divert to Wales. Undeterred, Anna hires a boat to continue her travels to Cork, but the storm proves too severe, and she finds herself stranded in a charming little seaside village named Dingle. With resolve, Anna heads to a local tavern in search of help and encounters the grumpy innkeeper, Declan O'Callaghan (Gustavo Sánchez Parra). Initially reluctant to assist her, Declan eventually agrees to drive her to Dublin after facing his own financial struggles—his pub at risk of foreclosure. Their agreement is set for a hefty sum of EUR500.
As they set off in Declan's old, beat-up car, a clash of cultures begins. He pokes fun at her high-end Louis Vuitton luggage, calling it "Louie," and ridicules her belief in the leap year tradition. Their journey takes a comedic turn when they encounter a herd of cows blocking the road; Anna's attempts to clear the path result in her stepping in cow dung and inadvertently causing Declan's car to roll into a stream. On foot, their misadventures continue when they get a ride from three travelers who abandon Anna with her bags, leading to an unexpected confrontation as Declan demonstrates surprising strength to reclaim her belongings after a scuffle at a pub.
Their bond deepens as they arrive at a railway station, where they share a conversation about what items they would rescue if their homes were on fire. During this encounter, Declan shares an enthralling Irish legend about a woman who used a sleeping potion to escape an unwanted marriage—a tale that resonates with both of them. As night falls, they must stay at a local bed & breakfast where they pretend to be a married couple named "O'Brady-Callaghan,” engaging in playful interactions that spark emotions neither had anticipated, ultimately leading to a complicating intimacy that neither acknowledges.
The next day, while hitchhiking, they're caught in a hailstorm and seek solace in a nearby church hosting a wedding. Invited to the reception, Anna finds herself reflecting on her true feelings. After consuming too much alcohol, she faces an embarrassing moment but simultaneously questions her commitment to Jeremy and her growing attraction towards Declan. The tension culminates when Declan shares his own heartbreak—his previous fiancée eloped with his best friend and stole his mother’s cherished claddagh ring.
As they finally reach Dublin, Anna is taken aback when Jeremy proposes to her right in the hotel lobby. In a moment that feels surreal, Anna glances at Declan only to see him walking out of the hotel, prompting her to accept Jeremy’s offer. However, during their engagement party in Boston, the truth about Jeremy's motivations unfolds, shattering Anna’s expectations of their future together. In a pivotal moment, she tests the idea of grabbing only the essentials within 60 seconds, realizing her lack of attachment to Jeremy and his priorities.
Later, back in Dingle, Declan has made significant progress in his life, successfully running his tavern with help from the community. Anna arrives with newfound clarity; she has ended her engagement with Jeremy and confesses to Declan that everything she desires is in Dingle. When she proposes a future together without any strict plans, Declan initially steps away, making Anna think she has been rejected. In a moment of desperation, she rushes to a cliff, contemplating her path forward.
Declan reveals himself, having gone to fetch his mother’s claddagh ring, intending to offer it to her. His romantic gesture culminates in a proposal of his own on the cliffside, prompting a joyful acceptance from Anna. Their journey concludes with the two of them driving away in Declan's car, ready to embrace whatever adventures lie ahead, leaving their destination to fate.
