Breakfast at Tiffany's by Truman Capote
Isn't it a lucky week for courtesans? Maybe I have a thing for them or something.
Guy falls in love with neighbor who is a teenage call girl, 19 years old. Not only is she a reformed hick, she's also stupidly naive. Basically, she's been carrying messages from this mob boss who's in jail to his lawyer. She gets caught, but refuses to stand witness against a friend i.e. said mob boss. She is helped in fleeing the country, if one can call it that, because she really wants a free flight to Brazil.
In a nutshell, hot but stupid chick gets stupid guy friends to commit a felony, but no one gets caught so who cares. Besides, she's hot.
It's like The Great Gatsby or A Separate Peace in that it's a character study, except those authors had the common sense to kill off their characters.