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 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.
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.
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.