Greg comes down with the flu and Katie battles exhaustion trying to take care of him and the kids. Her exhaustion leads to a confrontation with the school's overbearing school crossing guard.

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 and Greg dislike Taylor's new boyfriend, so they attempt to use reverse psychology to drive a wedge between them, which later backfires. After Spencer's over-the-top vision for Oliver's first date with a girl from his ballet class bombs, Greg helps Oliver make up for it with a romantic gesture.

The Otto children are beginning to experience struggles in their love lives after jumping into the dating world: Oliver is forced to choose between his girlfriend and his friend Cooper who come from two different worlds; Greg must play the “bad cop parent” to halt the PDA between Taylor and Trip; and Anna-Kat tries to make her relationship with Franklin official, without his consent.

Katie enlists Angela's legal help to convince Chloe Brown Mueller to sign off on the venue for the Spring Gala, but Angela ends up cozying up to Chloe instead.

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.

Anna-Kat runs for the Green Chair position in the school election against Chloe Brown Mueller’s daughter, which results in Katie and Chloe turning their kids’ election into a feud of their own. Meanwhile, Greg becomes concerned that Taylor’s new friend Pierce is trying to steal her away from Trip, causing Greg to intervene and scheme to prevent it.

After the previous “fattest housewife” in Westport gets plastic surgery to lose weight, Chloe Brown Mueller rubs it in Katie’s face that Katie has now assumed that title. In order to get revenge on Chloe, Katie goes through great lengths to dig up bad photos of Chloe from high school.

Katie lands the perfect pawn to play on the insecurities of the Westport housewives when she convinces a hot young trophy wife named Harper to volunteer as room mom for Anna-Kat’s class, but she quickly shifts gears when Harper rejects Anna-Kat’s idea for movie night. Meanwhile, Greg enlists the help of the kids to get Katie’s mom, Kathryn, to take an interest in someone other than herself.

As Oliver and Taylor stumble through their love lives, Katie begins to miss the spontaneity and unpredictability of being young and in love. Meanwhile, Kathryn’s plan to soothe Oliver’s heartbreak backfires when she tracks down an old boyfriend, Dan, and he is not as she remembers. At the same time, Anna-Kat makes strides at school when Franklin is stuck at home with the chickenpox, forcing her to make a new friend.

Katie plans a “friend date” in hopes of reconnecting with Taylor and encourages Greg to attend self-help guru Johnny Diamond’s seminar with Oliver. Meanwhile, Anna-Kat takes extreme measures to secure her place as Katie’s favorite child.

Katie feels left out and slightly jealous when Greg becomes fast friends with the newest member of the Westport Historical Guild. Meanwhile, Oliver fears Cooper is ditching him when he sees on social media that Cooper lied about his weekend plans.

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.