Rebecca and Jack take Kevin, Kate, and Randall to the community pool on a hot day and quickly realize each child is going through their own struggles. Kevin auditions for his first Broadway play in New York and meets a determined actress who is less than impressed by him. Toby runs into his ex-wife while at a restaurant with Kate, which sends Kate into a spiral of self-doubt. William is mistakenly reported as a loiterer in Randall's predominately white neighborhood, which exposes deep-rooted issues of race.

Kate interviews for a new job that seems just about perfect, although it comes with a catch. Randall doubts his career choice and wonders if he followed the right path. Kevin and Olivia's relationship moves in a new direction. Rebecca and Jack are conflicted on what to do when Randall tests as a gifted child.

As Jack, Rebecca and the three kids make their way to Rebecca's parents' house for their traditional Thanksgiving holiday, an unforeseen detour occurs. Kate makes two drastic life-changing decisions. Kevin brings Olivia to Randall's house for Thanksgiving. Randall's heart is broken when he learns about a lifelong secret his mother has kept from him.

Kate, Kevin and Randall head to their family's cabin to get away after their chaotic family Thanksgiving. A very angry Randall finds comfort and explanation from his father, Jack. Olivia speaks a harsh truth to Kate, which drives a wedge between Kate and Kevin. Rebecca and Jack struggle with what to do when 9-year-old Randall tells them that he's been looking for his birth parents.

Kate struggles with her feelings in the aftermath of Toby's heart attack. As William begins to spend more time with Jesse, Randall has to get used to his father's new relationship. After receiving the news they're expecting triplets, Jack and Rebecca must find a way to afford a home that can accommodate three babies. Olivia unexpectedly resurfaces, throwing both Kevin and Sloane for a loop.