Amy catches her fiance doing the dirty with another of their coworkers. She cancels the wedding and decides to take the "trip of a lifetime honeymoon" to Italy, but she doesn't want to go alone. Without another option, she signs onto an internet "travel chums" website and her ad is answered by "Mallory." It isn't until she gets onto the airplane that Amy discovers Mallory is a man.

Mallory recently escaped from a mistake of a marriage. Rich and handsome, it's hard to sort through the gold diggers to find someone to spend the rest of his life with, someone to produce an heir with. On a bet with his cousin, he signs onto the Travel Chums website as a diversion.

The story is familiar, but it is still a light-hearted romp through some of Italy's famous tourism attractions.