Emily attempts to secretly mold Jane into the perfect parent in order to name her as legal guardian to her kids should something befall her and Jason. Meanwhile, after attending her Aunt's funeral, Rosemary decides to throw herself a living wake so she won't miss out on all the fun when she's really dead.

In order to prove to her boss that she still has what it takes to be a great employee and that motherhood isn't getting in the way of her work, Jane does everything she can to hide the fact that she has the flu when the deadline to complete an important project is upon her. Meanwhile, a jealous Rosemary makes Horatio choose between being friends exclusively with her or a fellow nanny, and Emily's usually stoic husband, Jason, turns into her third child when he comes down with the flu.

Jane's week alone with Sophie turns out to be more stressful than she had hoped. Meanwhile, Rosemary tries to unionize Horatio's fellow nannies in order to get them better perks; and Emily and Jason's children don't like their "stay-cation" concept.

Jane feels like taking time off to be with her baby is as tough as being at work. Rosemary explains the need to unionize to Jane's nanny, Horatio. Emily and her husband decide to take a stay at home vacation this year, much to the disappointment of their children.

Jane heads to Annie's school to confront her bully, but when it comes to the workplace, she becomes the bully by using some tried-and-true techniques to get what she wants. Meanwhile, a newcomer is challenging Emily as head mom at the preschool. Also, Rosemary wants to get her 1980's band back together.

After Annie announces she is quitting her karate class, Jane rejoins a kickball at work to teach her a lesson regarding staying on course. Emily and Jason worry about their son's imaginary friend's temperament, and Rosemary shows off her parenting skills at seminar.

Jane begins to doubt her parenting skills when Shep, her boyfriend, immediately his it off with Horatio and her children. Meanwhile, Rosemary gives Emily a lesson on carpooling after being challenged by a neighbor on her supremacy.2