With Katie’s 40th birthday fast approaching, her self-esteem starts to wane. So Greg encourages her to go out and enjoy a night on the town with the girls, even suggesting she leave her wedding ring behind for a night of faux-single, silly fun. Meanwhile, Angela receives devastating news that will turn Doris’ life upside down. While Katie is away, Greg enlists the kids’ help to create a birthday present that is a heartfelt reminder of how much she is loved.

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.

Katie reminds Anna-Kat that she is a strong, independent, young woman and encourages her to start standing up for herself when dealing with Taylor. Meanwhile, Oliver feels left out when Greg invites Lonnie, Trip and Franklin to join him at the Historical Guild's latest reenactment.