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.
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.
She asks the bartender, Declan (Matthew Goode), if there is a taxi she can hire to take her to Dublin. He gives her a card, and she uses her cell phone to call. He answers her call and all the men in the pub laugh. Declan says he’ll take her to Dublin tomorrow, for $500 Euros. Anna agrees, and also books a room for the night; the only place in town is the rooms above the pub. Declan takes her to a small room and Anna looks for a plug to charge her phone. With European plugs being different, she has trouble, then finds one to work, plugs it in…and the phone sparks, and all the power in the village goes out. She shouts “You fried my Blackberry!” and Declan answers, “You fried the whole village”.
Next morning, Declan barges in her room to tell her he’s about ready to leave, but Anna is only wearing her underwear. She is furious he walks in unannounced, and yells at him, then gets ready to go. Declan tells her she now owes him $600 euros, to cover her stay +damages. He takes her to a clunky old red car. The old men from the pub comment that it is a bad day to start a trip; then they contradict each other, trying to remember what the bad luck is, either black cats or black magpies, and they discuss this while Declan and Anna depart.
As they drive, Anna tells Declan of her plans to propose on Leap Day. He laughs at her, while eating his sandwich, and tells her it is the dumbest idea, and if her guy wanted to marry her-he’d propose. She is furious, and throws his sandwich out the car window. Up ahead, their road is blocked by a herd of cows. Declan says to relax and wait, but Anna refuses, and shoos them out of the road. While doing this, she steps in cow poop and ruins her fancy shoes. Sitting on the car bumper, she tries to scrape the poop off, and the car rolls backwards. She and Declan try to stop it, but it is going too fast, and careens backwards down the road, and crashes into a pond. He is angry, and tells her to wait and they’ll eventually get a tow. Anna grabs her “Louey” rolling suitcase, and begins walking towards Dublin. She flags down a car, and a young man offers her a ride. She grins, and gives him her suitcase, and he puts it in the van, where she sees 2 other guys. Declan tries to warn her away from these guys, but she refuses to listen. Before she can get in the van, they speed off with her bag. She and Declan walk to the next town.
When they get to the pub, she sees the guy who stole her bag, and goes after him. Quickly the 3 surround her, and mean to do her harm, but Declan comes in, and defends Anna. They fight, and he wins and gets her bag back, and the thugs leave. Anna is grateful, and softens a bit towards him. They walk on to the next town and find there is a train that goes to Dublin in 2 hrs 45 min. While they wait, Declan wants to climb the hill nearby to see the view and the castle ruins there. Anna is afraid she’ll miss the train, but decides to go. At the top, the view is incredible and Anna can see the ocean. He tells her the story of the castle, and. then he asks her a question: if her house was on fire and she had about a minute, what would she save? She has no idea. He says he’d save his mother’s claddaugh ring. As they begin the walk back, she hears the train whistle. She runs down the hill, slips, and rolls all the way down and lands face first in the mud. They miss the train, and Anna cries.
The station master tells them that was the last train. They ask if there is a place they can stay, and he takes them to a B&B, which, coincidentally, is his house not too far away. His wife tells him they have one room available, as she kicked the last couple out as they weren’t married. Anna and Declan pretend they are married so they can stay the night. With just one bed in the room, they flip a coin for the bed. Declan tricks Anna into thinking she lost the bet. She takes a shower, and doesn’t know the shower curtain is almost transparent. When she gets out, she tells Declan it is his turn, and he tells her no chance since the curtain is see-through. She thinks he is joking…then is mortified to realize it is true, and he saw her in the shower. Declan laughs and smiles.
Anna and Declan make dinner for everyone at the B&B, to avoid eating the planned tripe for dinner. At dinner, the guests ask Declan and Anna to kiss. They give each other a quick peck, but the Irish stationmaster bangs his fist on the table and tells Declan to really kiss her. He turns and gives Anna a very passionate kiss. They both look at each other afterwards, in surprise, and almost smile.
Declan and Anna go to their room to go to bed, and since the shower is still wet, Declan can’t sleep there and Anna says he can share the bed with her. They stay far apart, but both roll over to look at each other, and are confused by what has happened and their growing feelings for each other. They go to sleep, and awake in the morning, with Declan’s arm around Anna.
They ask the stationmaster/innkeeper what time is the bus to Dublin, and he tells them there are no buses or trains on Sunday. They have to wait another day. Anna is frantic; Sunday is Feb 28th, and she will just barely make it to Dublin in time by waiting’ till Monday. While they wait, they go to a wedding in town, and stay for the reception. Anna is touched by the Irish toast the bride gives the groom: “May you never steal, lie or cheat. But if you have to steal, then steal away my sorrows. If you have to lie, then lie with me all the nights of our life. If you have to cheat, then cheat death because I don’t want to live a day without you”. Anna has a wonderful time and dances an Irish dance with Declan. During it, her shoes flies off and hits the bride in the head. She apologizes and the bride forgives her. As Anna sticks out her hand to shake the bride’s hand, she knocks over a glass of red wine on the bride’s white dress. Mortified at her clumsiness, she takes a bottle of whiskey and heads alone to the rocky shore of the lake, and drinks herself drunk. Declan finds her, and she throws up on his shoes, and he carries her back to town.
In the morning, the two are asleep on a bench near the train station, with Anna resting her head in his lap. She awakes, and leaves Declan asleep on the bench. He hears the bus and wakes up. Anna is nowhere to be seen, and the bus leaves. He fears she is gone, and looks sad. Anna comes out of the pub with 2 cups of coffee. He tells her she missed the bus, but she says she knows, and there is another one in 20 min.
On the bus to Dublin, Declan tells her his prior fiancé is there. She and Declan and Declan’s best friend opened the pub and it was going great…until she left Declan with the friend and those two went to Dublin. He is sad that she still has his mother’s claddaugh ring. Anna tells him she should go get it back. He looks away.
In Dublin, she goes to the hotel ATM to get Declan’s money. She tries to pay him, but he refuses it after all. They say good bye and turn and leave, but each stops. Declan turns first, and looks at Anna, and calls her. She turns, and they both look in love with each other, but before Declan can say anything, Jeremy calls out to Anna and comes and hugs her. He thanks Declan for getting Anna safely to Dublin. Then, he drops on one knee and proposes marriage to Anna. She is torn between Declan and Jeremy…and then says yes. Declan turns and leaves. Jeremy also tells Anna that he heard from the Davenport, and they are approved to buy the beautiful condo they wanted. Outside, Declan makes a phone call in a phone booth, and goes to a pub. A girl shows up, and says she is so surprised he called. She is the same girl from the photo at the pub; his ex. They talk and smile.
There is an engagement party for Anna and Jeremy at their new condo back in Boston. It is beautiful and Anna seems happy. Jeremy tells Anna and their friends that the reason he proposed was that the people from the Davenport made it clear that if they were married, they’d be approved. So, to get the condo, he proposed. Anna is crushed that that was Jeremy’s motivation to propose, and not love. She looks very sad at the party. Suddenly, the fire alarm goes off, and Jeremy tells everyone to leave. He tells Anna he needs to grab the laptop computer and the video camera. Anna realizes there is nothing she wants to save, and she calmly walks out and is gone.
In Ireland, the pub is about to close from financial trouble, and they are having a fundraiser to save it. Food and beer are being served, and it looks like it isn’t enough. The landlord is about to kick Declan out, when the old Irish men who drink there everyday start adding money to the collection jar. Enough is collected, and the landlord leaves. They cheer, and Declan says drinks are on the house. Once inside, dinner is served to a large crowd. One of the waiters tells him that a customer is complaining that the chicken is too dry. Declan is mad, and goes out to see who the troublemaker is. It is Anna. She asks him to be nice to her, and she just flew 3000 miles to see him, and tell him things didn’t work out with Jeremy. She asks him if he’ll NOT make plans with her, and give their relationship a chance…and she waits for an answer. He turns and walks away. She is so sad, and says that that must be an Irish “no”, and runs out of the pub, and down the road. Anna ends up at the giant cliffs, overlooking the ocean, crying. Declan shows up, and says “Just where in the hell are you going?” Anna replies that he said no, so she left. He says that he didn’t say no…he went to get something. He shows his mother’s claddaugh ring, and then drops to one knee, and says that he rejects her proposal to NOT make plans, and says he wants to make plans with her, and then says “Will you marry me?” Anna says yes, and they share a passionate kiss on the cliffs.
They are driving in the old red car again, and as they drive away, the back of the car has “Just Married” on it, and her “Louey” strapped on the roof. They drive off on their honeymoon.
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