Leap Year

Successful real estate agent Anna Brady is feeling frustrated as her cardiologist boyfriend Jeremy Sloane has yet to propose after four years of dating. This lack of commitment pushes her to take drastic action to change the course of their relationship.

Driven by her desire to propose, Anna plans a trip from Boston to Dublin on February 29, a day she believes holds special significance for proposals due to an Irish tradition. Her intention is to catch Jeremy off-guard and ensure he accepts her proposal.

During her flight, a severe storm forces the plane to divert to Wales instead of reaching Dublin. This unexpected turn of events complicates Anna's plans as she must find a way to continue her journey.

Anna hires a boat to take her towards Cork, a necessary step in her journey despite the stormy weather. However, she is ultimately put ashore at the seaside village of Dingle where her adventure truly begins.

In Dingle, Anna meets Declan O'Callaghan, a surly innkeeper whom she enlists for help. Initially reluctant, he agrees to drive her to Dublin for a fee, creating an uneasy partnership forged out of necessity.

Anna and Declan set out on their journey in his old car, and their contrasting personalities clash from the start. Declan mocks her expensive luggage and Anna's belief in the leap year tradition, setting the stage for further conflict.

As they travel, their trip is hilariously disrupted by a herd of cows blocking the road. Anna attempts to assist in moving the cows but ends up stepping in cow dung, leading to a series of comical mishaps.

The duo unexpectedly encounters three thieves rummaging through Anna's luggage at a roadside pub. Declan's surprising strength comes to light as he confronts the thieves, igniting a chaotic, yet bonding experience between them.

After a detour to a nearby castle, they realize they've missed their train. The experience leads to heart-to-heart discussions about regrets and dreams while strengthening their connection during their shared adventure.

Staying at a local bed & breakfast, Anna and Declan pretend to be a married couple to secure a room. Their staged intimacy ignites unexpected feelings, culminating in a forced kiss that stirs emotions neither are ready to confront.

Caught in a hail-storm, they seek refuge in a church hosting a wedding, where they are invited to the reception. However, Anna finds herself questioning her feelings for Jeremy, realizing her growing attraction towards Declan.

After numerous adventures, Anna and Declan finally arrive in Dublin, though tension lingers as Declan shares a painful story from his past. Their journey brings them closer, yet Anna's original intent remains clouded.

Just as Anna feels connected to Declan, Jeremy unexpectedly proposes to her in the hotel lobby. Caught between her old life and burgeoning feelings for Declan, Anna accepts, complicating her emotional state even further.

During her engagement party in Boston, Anna realizes that Jeremy's proposal was motivated by practicality rather than love. In a moment of clarity, she pulls a fire alarm, testing the urgency of her own true feelings.

Returning to Dingle, Anna confronts Declan at his tavern, confessing that she ended her engagement with Jeremy. In a surprise twist, Declan proposes to her on a cliffside, solidifying the deep bond they forged during their travels.