The Babysitters is a 2007 independent film directed by David Ross. It stars John Leguizamo, Cynthia Nixon and Katherine Waterston. The story follows a teenager who turns her babysitting service into a call girl service for married men after fooling around with one of her customers.
The movie begins with a voice over by Shirley Lyner (Waterson) as we see a cabin with mostly middle-aged men and teenage girls in various states of undress. In the narration she explains that this is her babysitting service, and then dismisses violence as a cause for why she started it.
Flash back to several months prior, Shirley is obsessively arranging items in her room when Michael Beltran picks her up for a babysitting job. She shows obvious signs of being attracted to him. After the babysitting is finished, Michael drives Shirley home and they stop into a diner to eat, where they flirt heavily and Michael admits frustration with how his wife has changed and Shirley says she doesn’t have a boyfriend because she finds guys her age to be too immature. She also admits to being an obsessive compulsive cleaner and organizer.
At school we meet Shirley’s friends: Melissa, a confident, sarcastic junior trying to get into Brown a year early, and Brenda, a very chatty girl who seems to have confidence problems.
The next babysitting outing, Michael and his wife Gail are meeting with Michael’s friend Jerry, who has a business offer for Michael. Gail is frustrated that Michael wants to take it, while Michael gets curious about an abandoned train yard behind the restaurant that Gail shows no interest in. When Michael is driving Shirley home that night, they stop at the train yard and explore it, eventually sharing a kiss. Michael pays her some extra money not to tell anyone about the kiss. On the next babysitting job, they actually have sex.
At school Melissa eventually wrings the truth about the babysitting outings from Shirley, who admits the extra money is nice. At the same time Michael confesses the wrongdoing to Jerry, who sympathizes with him. Soon, Michael asks Shirley if any of her other friends can “babysit” and Melissa volunteers. After Melissa’s outing, Shirley asks her for 20% of the money as her cut, which Melissa agrees is fair. They eventually convince Brenda to take a babysitting job and Melissa pushes Shirley not to warn her about the expected sex. At first it shocks Brenda, but the man with her is very reserved and nervous, eventually boosting Brenda’s confidence. The next day, Brenda agrees to the terms and the girls set up a working business, going so far as to have business cards printed up. Meanwhile, Michael is continuing to have trouble at his job and learns that Shirley is babysitting for others besides him, which makes him uncomfortable. His wife is suspicious of his continual long nights at the office, but he denies wrongdoing.
The first problem arises when Brenda invites her younger stepsister Nadine into the group without checking with Shirley. Nadine is much more rough and aggressive than Brenda and questions why Shirley gets a cut. She soon starts her own competing business behind Shirley’s back, and Shirley starts to lose customers while seeing Nadine and her friends wearing designer clothes and jewelry. Melissa suggests breaking into her locker to find proof and they enlist Michael’s help. When they find no evidence in Nadine’s locker, they vandalize the entire school to cover their tracks, making sure to target the lockers of other girls who were working with Nadine. Shirley meets with all of them and threatens more punishments unless they follow the rules. After the meeting, Melissa presents Shirley with fake permission slips for a trip to Jerry’s cabin for a weekend. The girls will be going under the make-believe of a school trip, while the men will be there on a “business retreat”.
At the party, Michael is increasingly uncomfortable with Shirley being with other guys while Jerry questions why Michael doesn’t go with any of the other girls. Jerry has supplied drugs at the party, and Brenda has a negative reaction to the seventh heaven. Jerry attempts to rape her, but along with Brenda’s verbal resistance and cries for her mother, decides not to proceed.
At her next babysitting job, Brenda has a collapse and runs out. When Shirley talks to her, Brenda says she wants out, which Shirley agrees with, but Melissa privately expresses worry that Brenda will talk. These worries are increased when Melissa is accepted to Brown. Michael’s wife confronts him about his distance and that he has been lying about his job situation, since he was just taken off of a major project. Michael finally voices some of his frustrations about the marriage, while Gail responds with hers.
On her own initiative, Melissa has several of their customers attack and threaten Brenda’s brother. Nadine assures Brenda that everything will be fine, while Shirley gets angry at Melissa and tries unsuccessfully to contact Brenda. Michael and Shirley, out at the trains again, have an argument where Michael tries to encourage Shirley to run away with him, while Shirley reminds him that this is just business and he’s cheating himself. He’s forced to abandon her when a cop shows up, and Shirley tries to contact Brenda for a ride. Upon hearing that Nadine is babysitting without her knowledge, she calls Melissa, who is with Jerry, and they go to confront her. They interrupt Nadine at a parking garage and nearly throw her off the roof. At that point, Shirley discovers that it is her own father that is with Nadine.
The scene cuts out to another voiceover by Shirley, who says that everything stopped and they all have to live with the consequences, though it is implied that no legal action resulted. The last scene is of Shirley parking across the street from Michael's house. She sees Michael interacting with his family, apparently trying to mend the gap.
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