After coming to terms with the fact that she must share her work bonus with Greg, Katie encourages him to live a little and the two decide to splurge on an overnight getaway. Meanwhile, Oliver’s attempt at a rebellious streak ends in disaster; and after letting Anna-Kat down, Taylor comes to the realization that she needs to step up and be a better big sister.

When Katie gets sick, Greg enlists Kathryn's help in taking care of the kids, but Kathryn leaves the kids to fend for themselves while she entertains an old high school boyfriend. Meanwhile, Taylor gets a taste of her own medicine when she tries to help an unruly Katie.

Much to Katie’s dismay, Anna-Kat becomes best friends with Chloe Brown Mueller’s daughter, Penny. When Katie takes extreme measures to avoid Chloe and keep the girls apart, Anna-Kat and Penny are forced to take matters into their own hands. Meanwhile, Greg encourages Oliver to be honest with his girlfriend and not hide his passion for ballet.

With the kids away at the school dance, Katie and Greg look forward to a romantic evening alone; but Anna-Kat is crushed when the boy she likes doesn’t ask her to the dance, and Oliver begins to panic when the town psychic’s predictions begin to come true.

Frustrated by the lack of appreciation for all she does, Katie decides to go “full Westport” and leaves the family to fend for themselves. Katie’s plan quickly backfires when the kids seem to be doing just fine, leaving Greg to suffer the brunt of her absence.

Katie ignores Greg's warning and takes Anna-Kat through a terrifying zombie-themed maze at the annual Halloween carnival. Once inside, Katie quickly regrets her decision and sends Anna-Kat to find help. Meanwhile, Greg has entered a pumpkin carving contest and is ready to go head-to-head against the previous year's winners.

In an effort to stay connected, Katie and Greg look into activities that they can enjoy as a couple. Meanwhile, Anna-Kat has her own hurdles to overcome when Franklin shines at square dancing and she fails miserably. Plus, Tripp struggles with the idea of Taylor going away to college.