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.

The dynamic of Randall and Kevin's rocky relationship is explained. Beth and William spend time together, which unexpectedly brings to light a secret William has been keeping. As Rebecca gets back to work for the first time in years, both she and Jack acknowledge that there is distance between them. Toby is caught straying from his diet regimen, throwing Kate into crisis.

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.

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.

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.