The Babysitters is a film of many themes: entrepreneurism, how people change in marriage, crushes, family, and teen prostitution. What starts out as an innocent schoolgirl crush on an older man between Shirley Lyner (Katherine Waterston) and Michael Beltran (John Leguizamo) soon becomes something much more.
It's instigating factor has nothing to do with Shirley, her beauty or her personality but rather Michael’s increasing dissatisfaction with his marriage to his wife Gail (Cynthia Nixon). In Shirley, Michael sees a reflection of the way Gail used to be (carefree, laconic) before their marriage. Michael finds certain aspects of his neglected personality, his love of trains for instance, given attention and interest by Shirley. Shirley’s intellectual interest in Michael eventually spawns physical interest, which is forbidden not only because Michael is a married man but because it’s against the law.
After a key moment in their inappropriate relationship where it turns from a possible romance to just a business arrangement, the idea for turning what just happened into a business is born. This is also the point in The Babysitters that some might find distasteful since not only does Shirley start prostituting herself to her babysitting clients, she’s a junior in high school and under age. Soon Shirley starts receiving so many requests for her “babysitting” services, she has to hire more high school students as "staff" to help meet the demand. Since Shirley is the person setting up the appointments, she receives twenty percent from each referred job and in effect, becomes a madam.
Teenage boys can rationalize sex as a physical act for pleasure. It’s rare to see teenage girls rationalize it in a similar way on screen, discounting films like Kids. The girls in The Babysitters rationalize sex to an even baser level. Business. It’s all just business.