Jean Webster 
Jerry Junior 

Jerry (Junior) is a wealthy upper-class American, a handsome young man whiling away several days in an Italian village, waiting for his sister and aunt to arrive. He’s getting very bored, so when the hotel waiter tells him about a lovely young American woman staying in a nearby villa, he decides to drop by (without an invitation or introduction, gasp!) and meet her. Unfortunately, Jerry and Constance get off on the wrong foot, and she dismisses him without a whole lot of thought. Jerry, angry and a little humiliated, is about to leave town when he overhears Constance discussing him with her father at the hotel’s restaurant, admitting he was handsome and slightly regretful about how it played out. Since Jerry’s attracted to her, he decides not to leave town after all. When he also overhears her asking for an Italian guide for some hiking the next day ("He must have curly hair and black eyes and white teeth and a nice smile; I should like him to wear a red sash and earrings.") Jerry – in a burst of dubious inspiration – decides to disguise himself as their guide (though he speaks almost no Italian). (Goodreads)