Some of us don't mind that our hero, playboy Tom (Patrick Dempsey), is one of New York's most notorious womanizers; others consider him incapable of turning a new leaf. But no matter where our hopes and suspicions fall in this man's only shot at true love, conclusions aren't likely to land too far from the tree.

In their thirties, Tom and Hannah (Michelle Monaghan), the two best friends, are supporting each other through times of uncertainty.

Just as Tom's interest in encounters with the opposite gender wanes, he watches his father taking his vows with his seventh wife.

Hannah on the other hand, while all good humor and warmth, has grown weary of a romantically stifled lifestyle.

A business trip to the miserable lowlands of Scotland leads to Scottish millionaire Colin (Kevin McKidd) whisking Hannah away.

With marriage preparations being hurriedly organized, Tom finds himself ordained the maid of honor, and in a struggle on all levels to outdo the wonderful groom Colin.

We expect our hero's rival to show his villainous side. Instead, the finger of blame and ridicule ends up each time pointing to the charismatic heartbreaker himself, as he bids to vouch for Hannah's hand.

By the end of the film, Hannah remains more of a new breed of trophy than the independent-minded articulate animal rights activist her character is painted out to be.