Gene is a rich woman-child whose wild lifestyle has landed her under house arrest; Billie is a down-on-her-luck Harvard grad who has been hired to babysit; debauchery and depravity ensue.
Gene tries to have Billie fired after Billie forces her to complete a book report; Billie convinces Kent that he should be firmer with his daughter.
Gene gets a temporary release from her house arrest to attend a funeral, but she and Billie take a few detours on the way there thanks to Gene's unfettered enjoyment and Billie's fear of funerals.
The quarterback of a pro football team visits the house for a weekend which sparks an intense romantic rivalry between Billie and Gene.
While the mansion undergoes fumigation, Billie and Gene camp out in the guest house.
Gene's birth mother arrives at the house unexpectedly, generating intense emotions in Kent. Meanwhile, Billie goes on a date with a dental hygienist who has a surprising wild side.
Gene plans a prom for GED students and invites her cyberbully in order to humiliate him in public. Meanwhile, Billie's escort is a fellow tutor whose GED student is younger than she imagined.
Billie gets Joy fired by accident, so she and Gene try to persuade Kent to rehire her by holding a series of civil protests.
Billie's awful ex-boyfriend comes over for dinner, so Gene pretends to be a butler to show him how well Billie's been doing since they broke up.
Gene takes her GED, while Billie aims for her dream of being a college professor.
