Claudine Nineteen by Paul Rachman

Claudine is an au pair in 1980s New York City, who has been stuck in her mostly no-wage job for way too long.  She dreams of traveling the world and approaches everything she does on her own unique terms.  Seeing no other options to realize her dream, she crafts a high-end shoplifting scheme. Suddenly, Claudine is put in charge of Henry, a shy, awkward teenage boy who suffers from extreme anxiety and fainting spells, and recruits him into her secret criminal life. The events over their weekend together give Henry the confidence he's lacking, due to his absent and controlling mother, and Claudine the empathy she needs.