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.

Katie grows concerned when Anna-Kat is invited to join Westport's elite scout troop, The Wildflower Girls. Meanwhile, Taylor learns her Carnegie Mellon interview is scheduled with famous alumnus and Broadway star Brecken Phillips ; and, Oliver befriends the school recluse, Trevor.

When Katie learns that the top prize is an all-expense paid vacation, she doubles her efforts to help Anna-Kat win top prize in cookie sales against her fellow troop members, The Wildflower Girls. Meanwhile, Oliver's attempt to help a student he befriends through the Teen Help Line center backfires.

Greg ropes Katie into a double date with Principal Ablin and Maria in an attempt to further his political aspirations. Meanwhile, Anna-Kat’s newfound popularity at school proves to be overwhelming.