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As the Otto family ushers in a new era, Katie and Greg make the emotional decision to sell the family minivan; Daniel suffers a setback that forces him to rethink how to accomplish his goals.

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Katie's life is turned upside down when her notoriously elusive boss Whitney pops into town and promotes Katie; a colleague's death pushes Greg toward an existential crisis.

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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.

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Greg hosts a meeting for the Westport Historical Guild to welcome back Stan, and Katie’s homemade lasagna is a huge hit with the guys. After Stan makes several trips back for seconds and begins spending an inordinate amount of time at the Otto house, Chloe Brown Mueller becomes convinced that Katie and Stan must be having an extra-marital affair. Meanwhile, Angela and Doris step in to help Oliver with his Teen Help Line.

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Katie ignores Greg's warning and takes Anna-Kat through a terrifying zombie-themed maze at the annual Halloween carnival. Once inside, Katie quickly regrets her decision and sends Anna-Kat to find help. Meanwhile, Greg has entered a pumpkin carving contest and is ready to go head-to-head against the previous year's winners.

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With Katie’s 40th birthday fast approaching, her self-esteem starts to wane. So 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 faux-single, silly fun. Meanwhile, Angela receives devastating news that will turn Doris’ life upside down. While Katie is away, Greg enlists the kids’ help to create a birthday present that is a heartfelt reminder of how much she is loved.

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Katie teams up with Oliver in hopes of growing her lasagna-making endeavor from hobby to serious business venture. Meanwhile, a bout of writer's block forces Greg to look at new career opportunities. When a young YouTube sensation enlists Greg's help to ghostwrite his memoir, Greg is pushed out of his comfort zone.

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Katie's feud with Chloe Brown Mueller is reignited when Oliver discovers Chloe's attempts to sabotage Katie's lasagna business. Meanwhile, Anna-Kat and Franklin play matchmaker for Principal Amblin in an attempt to secure more privileges.

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In an effort to stay connected, Katie and Greg look into activities that they can enjoy as a couple. Meanwhile, Anna-Kat has her own hurdles to overcome when Franklin shines at square dancing and she fails miserably. Plus, Tripp struggles with the idea of Taylor going away to college.

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Katie looks forward to sharing her favorite childhood 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.