Katie goes to great lengths to appease Principal Ablin in order to ensure Taylor graduates high school. Meanwhile, Greg finishes ghost writing the final chapter of Lonnie's book. And while Oliver is devastated to learn Cooper's family will be moving out of Westport, Anna-Kat tells Franklin she is ready to venture outside her comfort zone and plans to attend sleep-away camp during summer break.

Without her lasagna business to keep her preoccupied, Katie feels like her life is once again off course. As she searches for purpose, she redirects her energy toward Greg and the kids becoming overbearing and controlling. Franklin challenges an older boy to a duel in an effort to win back Anna-Kat's affections.

Katie is taken aback when she learns Taylor's boyfriend Trip has been spending the night. Greg is forced to separate the kids when Anna-Kat and Franklin both come down with mono. And when Oliver starts spending too much time at the office, Cooper begins to feel neglected.

With Anna-Kat and Franklin home with mono, Katie seizes the opportunity to use them as the backdrop for her mommy vlog. And when Taylor's first college paper comes back with an A, Greg questions her TA's intentions. Meanwhile, Cooper helps Oliver renovate the basement.

Katie pushes Anna-Kat and Franklin to take a risk and try an activity outside their comfort zone in order to create new content for her mommy vlog. Meanwhile, Oliver is convinced taking performance-enhancing drugs will help him ace his SATs. And after bonding with her TA over an art exhibit, Taylor begins to wonder if Trip is the right guy for her.

When Katie’s mentor and dear friend Tami moves to Westport, Katie wastes no time introducing her to her “A Real Mother” vlog viewers. Meanwhile, Taylor discovers Greg has been keeping an entertaining secret.

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.

Katie and Tami make fast friends with J.D., a luxury hotel manager whose promise of access to complimentary hotel rooms around the world sounds incredibly enticing. However, Katie’s travel fantasy comes to a screeching halt when she learns J.D. is an aspiring first-time father who’s counting on her for parenting guidance.

Katie goes overboard in her efforts to help J.D. become a father. Meanwhile, after a brush with the law, Greg worries Taylor may be a political liability.

To celebrate the momentous 100th episode milestone of his podcast, Franklin invites Katie and the family to make guest appearances on his show, “Getting Frank with Franklin.” After witnessing his intrusive tactics with Taylor and the others, Katie is determined to keep her interview light and fun but is surprised when her mom Kathryn joins her. Meanwhile, Greg asks Lonnie to be his campaign manager to help strengthen his social media presence.

Katie and Greg secretly put Kathryn through a series of tests to see if she would make a good guardian for Anna-Kat in the unlikely event something should happen to them. Meanwhile, after tracking down J.D.’s potential egg donors, Tami and Katie scheme to learn more about them.

Katie plays matchmaker by impersonating Oliver on his social media account to win over a girl. Meanwhile, Lonnie helps Greg dig up dirt on his political rival.