Uptight [[UsefulNotes/{{Boston}} Bostonian]] Anna (Adams) travels to Ireland hoping to propose to her boyfriend (Adam Scott) because according to Irish tradition a woman can propose to a man on February 29 during a leap year and said boyfriend happens to be attending a convention in [[InDublinsFairCity Dublin]]. Unfortunately bad weather forces her plane to divert to Wales and when she tries to reach Ireland by boat she ends up dropped of at Dingle (about as far away from Dublin as you can get while still being in Ireland). She ends up hiring local innkeeper Declan (Matthew Goode) to drive her to Dublin so she can get there by the 29th. HilarityEnsues.

The film has not been greeted with universal acclaim, especially by Irish critics who were left frothing at the mouth at some of the outdated [[{{Oireland}} Oirish]] stereotypes it employed.

If you're looking for the trope about the 29th of February, see LeapDay.
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!! This film contains examples of the following tropes:

* TheAllegedCar: But remember: "It's a classic"
* CannotStandThemCannotLiveWithoutThem: Anna is originally less than thrilled about relying on Declan for a ride...that changes.
* CityMouse: Anna. 
* ComfortingComforter: When Anna wakes up on the bench, she sees that Declan has given her his coat as a blanket. When she rises, she places it tenderly across his body.
* CuteClumsyGirl: Anna is more than a little klutzy.
* TheDitz: While not totally stupid Anna ''is'' kind of an airhead.
* FakeIrish: Matthew Goode.
* FourthDateMarriage
* HappilyMarried: The owners of the B&B and their Italian guests
* {{Hatedom}}: Amongst Irish movie critics. One called it "offensive, reactionary, patronising filth". [[http://www.culch.ie/2010/03/03/leap-year-is-a-time-travel-rom-com-possibly-set-in-lost-universe/ This review is roughly as favourable, but much funnier.]]
* HeyItsThatGuy: Anna's best friend is [[ItsAlwaysSunnyInPhiladelphia Sweet Dee]] and her father is the [[ThirdRockFromTheSun High Commander]]. 
** Also, Declan is [[{{Film/Watchmen}} Adrian Veidt]].
* IrishNames: The films best joke, at least for Irish audiences.
-->''Anna reads the name 'Eoghan' on a bartenders shirt.''
-->'''Anna:''' Hello, um, E..o..g..h..a..n?
-->'''Eoghan:''' ''Owen''.
* KissingUnderTheInfluence: Averted. ''Juuust'' when we think drunk Anna is going to kiss Declan on the beach in the moonlight. . .she pukes all over his shoes. 
* LeapDay
* LoveConfession: Both Anna and Declan have one at the end
* {{Oireland}}: Played absurdly straight. Even uses the phrase "Top of the Mornin' to You" unironically.
* MoneyDearBoy: Matthew Goode claimed he only did this film for the money and so he could visit his family more often.
* OohMeAccentsSlipping: Some people though Matthew Goode was doing a great ''Welsh'' accent (he's supposedly from Kerry). 
* OppositesAttract: Refined (if ditzy), uptight fashionista Anna and slobby, [[{{Dismotivation}} aimless]] Declan.
* RoadMovie
* RomanticFalseLead: Obvious, since Adam Scott is not even on the front cover
* RunningGag: "Just put 'em in the wash. They'll be grand."
** Also, refering to Anna's suitcase as "Louis."
* SleepCute: ''Twice.'' First when they fall asleep on the bench, Anna's head pillowed on Declan's lap. Then again right after on the bus with her head on his shoulder.
* TallDarkAndHandsome
* YouFailGeographyForever: Anna sets off by boat from Cardiff, aiming for Cork, even though she actually wants to go to Dublin. A storm forces the boat to put in ''Dingle'' (consult a map of Ireland). 
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