After spending years as a full-time mom, Katie goes back to work as a party planner, which brings new challenges of balancing home and work life into the mix.

With her new job taking up more of her time, Katie and Greg try to split up parenting duties. Katie over-involves herself in Taylor's social life by trying to keep some distance between Taylor and her boyfriend, Trip, to make sure Taylor is her own person aside from him. Meanwhile, Greg tries to convince Oliver to be honest after overhearing Oliver lie to his friends about his less-than-luxurious summer vacation.

While Greg enlists Oliver and Anna-Kat’s help to drum up new recruits for the Westport Historical Guild, Katie does her best to support Taylor’s dreams of becoming the next American Idol.

Katie's life is turned upside down when her notoriously elusive boss Whitney pops into town and promotes Katie; a colleague's death pushes Greg toward an existential crisis.