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.

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.

The Pearson family finds themselves at the hospital on Christmas Eve after little Kate comes down with appendicitis. When they run into Dr. Katowski, who is alone at the hospital, they realize they need to be there for him as much as he was once there for them. Presently, Kevin celebrates Hanukkah with Olivia and her family, Kate continues to pursue her big surgery and someone from William's past reappears in his life.

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.

Jack and Rebecca get in over their heads when they decide to throw Kate, Kevin and Randall three separate parties for their 10th birthday. Randall struggles to make time for William as things intensify at the office. Kevin makes a major decision in his romantic life. Kate's gastric bypass journey takes an unexpected turn.

As Kevin stresses about the premiere of his play, he receives support from an unexpected source. Randall struggles under the pressure of both his work and ailing father. Rebecca and Jack's Valentine's Day doesn't go as planned. Toby and Kate decide to dig deep and get to know each other's biggest secrets.

The entire Pearson family gathers at Randall's for an unusual party. Kevin and Sophie's relationship deepens on the night of his play's premiere. Kate struggles to open up to Toby about her father's death. Tensions are high between Jack and Rebecca as she leaves on tour with her band.