Tom Leezak (Kutcher) and Sarah McNerney (Murphy) are a young couple unexpectedly swept off their feet after their first meeting. Tom is a late night radio traffic reporter whose good looks, blue collar lifestyle and unrelenting passion for sports makes him the ultimate alpha-male. Sarah is a beautiful, free-spirited writer whose family is as wealthy as it is snobbish.
Much to the surprise of Tom’s friends and the dismay of Sarah’s family, the two quickly fall in love. Tom’s attempts to assimilate himself into Sarah’s world of privilege and expectations fall short, but Sarah ignores her father and sister’s incessant attempts to dissuade her from following her heart and marrying her knight in rusty armor.
Following their wedding, the happy couple sets off with the highest of hopes and ideals about love and marriage, on what they expect will be the perfect vacation in Italy. But thanks to Sarah’s wealthy ex-boyfriend and a relentless string of bad luck, the happy couple experiences a honeymoon from hell that tests the limits of their young love.