When uptight Harvard graduate Billie interviews for a nanny job, she's surprised to learn that her charge is Gene, a grown woman on house arrest. Billie soon realizes that party animal Gene really does need a babysitter.

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 is granted a temporary release from house arrest so that she can attend a funeral. On the way there, Gene's excitement at finally being out in the real world and Billie's fear of funerals lead them to make a few unplanned detours.

The quarterback of a pro football team visits the house for a weekend, sparking 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 decides to organize a prom for GED students and invites her cyber bully in the hopes of publicly humiliating him. Meanwhile, Billie's date is an attractive fellow tutor whose GED student turns out to be much younger than she initially thought.

After Billie accidentally gets Joy fired, she and Gene stage a series of civil protests in order to convince Kent to rehire her.

When Billie's obnoxious ex-boyfriend comes over for dinner, Gene poses as a butler in an attempt to convince him that Billie has been prospering since their breakup.