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What lengths must a woman go to and what limits must she push, to secure her man’s affirmation to marry her? Seems bizarre if you think about how it is something of a given that the man is the one who should ‘pop the question’ if a serious relationship is heading towards marriage. But in the movie Leap Year, directed by Anand Tucker, the ‘option’ opens up for women in Ireland according to Irish tradition on of February 29 every leap year, to propose marriage to a man. And the man is said to be compelled to accept it!
When her steady boyfriend of many years – Jeremy shows no signs of yet proposing to her Anna Brady grows frustrated at the lack of initiative on his part to make a commitment to marriage. The two of them are even making a ‘living in’ arrangement as well in an upscale exclusive-residential-apartment complex. But the good looking cardiologist has simply not got around to taking that big step, going down on one knee, and making Anna’s dream come true.

When Jeremy goes to Dublin to attend a conference,and it so happens that he will be there on the last day of February –the 29th which makes it a leap year day, Anna sees, what seems to her, is a providential sign that she can make him marry her after all. So, she decides to travel to Ireland and ‘pop the question’ herself! But after her flight hits a stretch of turbulence and the intervening circumstances leave her in a little Irish coastal backwater with quirky folks who have muddled up their local superstitions and abhor the thought of setting foot in Dublin, Anna finds herself in a race against time to make it to Dublin before February ends. She procures a surly, but handsome, Irish innkeeper, Declan O’Callaghan, as her transporter to take her to the capital going across the idyllic Irish countryside to make it in time to propose to her man, before the time lapses.

But Declan who thinks her idea is stupid and indicative of utter desperation, complies only because his pub is threatened with foreclosure, and he needs the money, the fee of 500 Euros. Worlds apart in their outlooks about life and what ranks as priorities, the journey soon finds a formidable hurdle in the nature of a herd of cows blocking the road.

A stark difference of opinion, and action, leaves the two of them finally stranded with no means of motor transport after the car rolls down the road and falls into a stream.
Pretending to give her a ride three hoodlums who drive by in a van steal Anna’s luggage. And eventually Declan and Anna reach a pub where they discover the thieves who rummage her luggage with crass boisterousness. Declan gets into a fight with them and they are all kicked out by the landlord. They reach on foot a railway station from which there is the hope of catching the train to Dublin. But after a time whiling stroll causes Anna to miss the train which arrives early the two are offered bed and breakfast at the stationmaster’s home. There is a quick improvise done there to please the conscience of the highly conservative host – the wife of the stationmaster. Declan and Anna say they are married since otherwise they simply wouldn’t be entertained there to spend the night.
The evening and the following morning create sparks of subtle attraction between the two pretending couple and the following day they go to Dublin by bus. In Dublin they go to a park and Declan tells Anna that the reason he hates Dublin is because his former fiancée is in the city. He had once been engaged. But she had run off with his best friend and his family ring to Dublin.

When they go to Jeremy’s hotel, Anna is completely surprised when Jeremy going down on one knee proposes to her. She accepts after a moment’s hesitation. She turns around to find Declan, dejected, walking away.

Back in the US at their engagement party, Anna learns that Jeremy had decided to propose marriage to her for what seem ‘not the right reasons’. It had been a calculated move to qualify to get the apartment they had applied for.

Back in Ireland, Declan is successfully running his pub-cum restaurant, after having saved it from foreclosure. A waiter tells Declan that a customer had complained about his chicken stew being dry and he stomps out to the restaurant to find out who had made the affronting remark. The answer, then leads to a turn of the story that would have at the point when Anna first walked into Declan’s pub seemed the unlikeliest of fates.