Morgan suggests that a man has been rehabilitated and aids in his parole, but later regrets his decision when the man murders someone days after being released.
When Doris goes into labor and Katie heads to the hospital to be with her, the Ottos struggle to be in the same place at the same time in order to open their Christmas presents together. Meanwhile, Taylor coaches Oliver on the best way to ask out a crush.
Katie and Greg dislike Taylor's new boyfriend, so they attempt to use reverse psychology to drive a wedge between them. 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.
Katie wants to prove to the Westport moms that she is fully capable of competing at Field Day at Anna-Kat's school, but ends up taking the competition a little too seriously. Greg enlists Taylor's boyfriend, Trip, to help him make the family recipe for chili in a local competition, which makes Taylor and Oliver jealous.
The Otto children begin 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.
