In the 'ideal' town of Westport, Kate Nixon is striving to raise her flawed family.
Drained Kate is struggling to balance between her children, schoolwork, and a sick spouse with a flu.
As Kate unwillingly participates in the annual Westport Zombie Run, Greg and Anna-Kat go too far with their costumes.
As Anna-Kat draws a giant plus-sized drawing of Katie for the school art show, Katie goes to recover it. On the other hand, when Katie goes away, Doris is left in charge of Oliver and Taylor, and sets out to discipline them.
To earn Anna-Kat an invitation to a famous girl's birthday celebration, Katie begins to behave like the other Westport mothers.
Things start to spiral out of control, when Katie's mother Kathryn comes over for Thanksgiving.
When Katie and Greg find that Dr. Ellie, Anna- Kat's special needs teacher, has been laid off, they get involved in PTA shenanigans to stop it from happening.
Oliver is developing his skills by taking classes, hoping to ask the girl he admires to go to the Westport Cotillion together. He also asks his father not to tell Katie about it.
Katie's festive joy is dampened when Viv forces her to participate in the school's Christmas show. Greg brings Taylor and Oliver to a nearby nursing home to cheer the patients up.
Katie and Greg are overjoyed that Anna-Kat has a playmate, until they discover that she's a kleptomaniac in the making.
The Ottos are trapped due to a snowfall without electricity, and Katie learns new things about Viv's life.
When Oliver informs his parents that he doesn't prefer to have a birthday party because of his parents' modest home, Katie organizes a surprise party for him anyway.
As the Ottos' house is put up for sale, Katie is the only one who is excited about the thought of leaving Westport.
Katie's minimal Valentine's Day preparations are disrupted by Greg's extravagant plans. On the other hand, Oliver buys a pricey present for the girl he likes, and Taylor tries to trick her parents into going to a party.
Greg forms a friendship with a fellow history geek, who also happens to be the husband of Katie's biggest rival.
As Katie decides to let everyone be and depend on themselves, she is shocked when they don't appear to want her assistance. Meanwhile, Katie battles a store manager over faulty garbage bags.
As Katie urges Viv to confront her obnoxious husband, Alan, Viv follows her advice and decides to leave him and stay with the Ottos.
Greg tries to encourage Katie and their daughter Taylor to live by his moto to "never give up". Meanwhile, Oliver's vision board is causing a stir.
Doris demands that Katie attend a charity polo match she is organizing, so Katie invites her college best buddy.
As Greg struggles to accept the idea that Taylor has a boyfriend, Anna-Kat informs her parents that all she wishes for her birthday is to be allowed to walk to the library on her own.
Katie must defeat her anxiety of wearing a swimming suit in public in order to assist Anna-Kat in overcoming her crippling fear of water. On the other hand, Oliver offers Greg a makeover.
After Celeste, Angela's ex, helps Greg sign a book deal, Angela is enraged when Katie and Greg spend the evening out with her.
Katie's plan to avoid parent volunteer work by claiming to be pregnant backfires, while Greg and Katie find out about Taylor's secret Instagram account.