As the Otto family ushers in a new era, Katie and Greg make the emotional decision to sell the family minivan; Oliver suffers a setback that forces him to rethink how to accomplish his goals.
Katie's life is turned upside-down when her notoriously-elusive boss Whitney pops into town and promotes her; a colleague's death pushes Greg toward an existential crisis.
When Anna-Kat's school lunch lady refuses to make simple eco-friendly changes in the school cafeteria, Greg puts on a show highlighting the importance of recycling with his friend and fellow environmentalist Bill Doty.
When Greg hosts a meeting for the Westport Historical Guild to welcome back Stan, Katie's homemade lasagna is a huge hit with the guys; Angela and Doris step in to help Oliver with his Teen Help Line interview.
Katie ignores Greg's warning and takes Anna-Kat through a terrifying zombie-themed maze at the annual Halloween carnival; Greg enters a pumpkin carving contest.
With Katie's 40th birthday fast approaching, her self-esteem starts to wane; 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 silly fun.
Katie teams up with Oliver in hopes of growing her lasagna-making endeavor from hobby to serious business venture; a bout of writer's block forces Greg to look at new career opportunities; Greg is pushed out of his comfort zone.
Katie's feud with Chloe Brown Mueller is reignited when Oliver discovers Chloe's attempts to sabotage Katie's lasagna business; Anna-Kat and Franklin play matchmaker for Principal Amblin in an attempt to secure more privileges at school.
Katie and Greg look into activities to keep them connected as a couple; Anna-Kat has her own hurdles to overcome when Franklin shines at square dancing and she fails miserably; Trip struggles with the idea of Taylor going away to college.
Katie looks forward to sharing her favorite Christmas tradition with Taylor, but a surprise visit from her mom threatens her holiday cheer; Greg is blindsided by Katie's good intentions; Oliver and Anna-Kat break a family heirloom.
Katie grows concerned when Anna-Kat is invited to join Westport's elite scout troop; Taylor learns that her Carnegie Mellon interview is scheduled with famous alumnus and Broadway star Brecken Phillips; Oliver befriends the school recluse.
Katie is determined to help Anna-Kat win top prize in cookie sales against her fellow troop members, The Wildflower Girls; Oliver's attempt to help a student he befriends through the Teen Help Line center backfires.
Against Greg's wishes, Katie sets out to play matchmaker for British Greg; Oliver goes along with a rumor at school about his sexual identity to help a classmate feel accepted; Anna-Kat considers throwing out her childhood toys.
Katie finds old furniture in the basement and tries to recreate her and Greg's first apartment; Greg enjoys an unexpected benefit of being the victim of Lonnie's relentless practical jokes; Doris recruits Oliver as her driver.
Katie begins to feel like a third wheel when breakfast talk starts revolving solely around Angela and Doris' new relationships; Greg struggles with Anna-Kat's newfound independence; Taylor and Oliver are horrified by an embarrassing photo.
Katie encourages Anna-Kat to stand up for herself when dealing with Taylor; Oliver feels left out when Greg invites Lonnie, Trip, and Franklin to join him at a reenactment of the Battle of Westport.
Against Greg's better judgment, Katy pushes Taylor to lighten up and participate in her school's senior prank; Anna-Kat asks Oliver to give Franklin a makeover so he won't embarrass himself at a classmate's party.
The Ottos go on vacation with Anna-Kat's prize: Katie tries for a kid-free day with Greg; Taylor gets conned in Hollywood and Anna-Kat must get them out of trouble; Oliver struggles to get Cooper to comprehend their financial disparities.
Katie confronts a classmate's mom when she suspects that Anna-Kat is being bullied; Taylor must complete the final item on her life-skills checklist so she can attend her senior prom; a girl on the teen helpline asks Oliver to prom.
