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.
Teenagers at Shirley’s age are full of awakened hormones and urges, regardless of gender. Rather than having sex with boys at school, which may or may not damage their reputations, the babysitter girls babysit, indulge their urges, keep their reputations intact (but for some, not their self-respect), and make money to save or buy their adolescent hearts’ desire.
The only babysitters that show an emotional response to what they are doing, that are emotionally affected by it, are Shirley and the third recruit to the babysitting team, Brenda (Louisa Krause). The emotional and physical toll begins eating away at Brenda, the luster of making large amounts of money for doing something pleasurable soon begins to fade and all that is left is the degradation she is freely submitting herself to. At one point, one of her would-be clients announces “it’s not worth it” and Brenda realizes that he is right, in more ways than one. This moment and its aftermath also served to bring The Babysitters down to earth as a whole. What started out as (a profitable) fun and games becomes grounded in the reality of the sex trade.
The cast of The Babysitters is good but it's Leguizamo and Waterston that do the majority of the heavy lifting in the film. David Ross’s The Babysitters turns sex conducted by the underaged for money into a film of consequences where the old adage “You reap what you sow” comes very much into play.