Plot: Slick stud Tom, a born womanizer, always had a boon for confident Hannah, the one who never fell for his cheeky charms but became his female confident, yen years after their college dorm days. He always waved his New York basketball mates' warning she wouldn't remain available endlessly for a serial dater. For her job as art prospector, she was on a six weeks mission to Scotland, during which Tom realizes he misses her around badly. To his horror, she returns with a Scottish perfect fiance, Colin, who already convinced her to move into his ancestral estate. While hesitating to make a last-chance move, baffled Tom accepts her invitation to act, lacking a girl buddy, as his 'best maid', inspired by his committed mates to attempt sabotaging Colin and convincing her he's the only soulmate. So he comes along to Scotland, where he's heir to the country's largest whiskey distillery, and a champion at everything, from hunting to Highland games, yet Yankee novice Tom must compete.
Alternative Plot: Always shy of commitment, Tom (Patrick Dempsey) lives as a serial dater. Hannah (Michelle Monaghan), his best friend, has wanted to marry and now has found Mr. Right -- just as Tom realizes he really loves Hannah. When she asks him to be in her bridal party, Tom seizes the opportunity to prevent the nuptials and woo her himself.
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