Despite pressure from Oliver, Greg and her rival, Tara, Katie insists she’s going to plan the Spring Gala her way. After Oliver is emasculated by his ex-girlfriend, Greg attempts to teach Oliver how to “man up” by throwing a successful barbeque.

Katie is worried that the launch of Greg's new book might go poorly, so she enlists Angela and Doris to write positive reviews; when the book unexpectedly does exceedingly well, Greg buys a new car without consulting Katie.

Katie and Greg struggle to resist the urge to micromanage as their children navigate life choices, such as landing your first job, picking out friends and managing homework.

When Katie's mom, Kathryn, comes to town, Katie and Kathryn encourage the kids to make less than favorable decisions: Oliver cheats in shop class and Katie helps him try to get out of it, while Kathryn reassures Taylor that she doesn't need to go to college.

Viv asks Katie to take Violet for the night so she and Alan can discuss reconciling but is caught off guard when Greg is hit with a bout of baby fever. Meanwhile, Taylor tricks Oliver into helping her when Luther eats an expensive pair of earrings.

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.