In Boston, Anna (Amy Adams) is shown decorating luxury apartments. She is a “stager” by profession: she puts furniture and accessories in empty apartments and houses, in order to make them look their best to sell. She meets her boyfriend, Jeremy (Adam Scott), a cardiologist, and together they go before the board of The Davenport, an exclusive co-op where they hope to be approved, and buy a condo.
Afterwards, she meets a friend for dress shopping, and while being fitted, her friend says she saw Jeremy coming out of a posh jewelry store, carrying a small signature red bag. They scream in excitement: this store is known for their engagement rings. Anna practices looking surprised, as they have a reservation for a fancy dinner out, since Jeremy is about to leave for a medical conference in Dublin.
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Before dinner, she meets her Dad (John Lithgow), for a drink and a visit in a Red-Sox bar. He is unkempt, and appears to be less than successful, but quite happy. He tells her that her grandmother proposed to her grandfather on Leap Day, and they were married and quite happy. He explains that on Leap Day, February 29th, a girl can propose to her guy in Dublin, and it’s a tradition. She laughs and says it is a silly custom.
At dinner, Jeremy pulls out a small box, and tells her to open it-she does, and is surprised to find it holds diamond earrings, and not an engagement ring. She smiles wanly and feigns enthusiasm. She is disappointed that it isn’t an engagement ring and proposal, after living together for 4 years.
After Jeremy leaves for his flight to Dublin, Anna looks on the internet for the Leap Day tradition, and finds out it really happens, and reads articles and watches video clips of proposals. She decides to do it, packs a bag, and books a flight to Dublin. She is seated next to a priest, and tells him her plans. As they near Ireland, they hit a bad storm, and must divert to Cardiff, Wales to land. Upon landing, Anna is amazed she cannot get any flights to Dublin, even after they tell her all the airports are closed. She takes a bus, and then a small tugboat to Cork, Ireland…but again, the storm messes her plans and she is taken and dropped on the beach in Dingle, Ireland. Anna takes her rolling Louis Vuitton suitcase, and starts walking. It begins to rain, and she is soaked. Eventually she finds a small village, and goes in the pub.
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