Content Warning: This section of the guide discusses racism, anti-Black biases, and anti-gay biases.

Meanwhile, Monk’s mother’s memory is getting worse, and Lorraine begins a relationship with Maynard. When Monk visits Marilyn, a man named Clevon opens the door. Monk shakes hands with him but leaves soon after. Later, Marilyn tells him that she and Clevon used to date but that they are breaking up.

Soon after, Monk visits a clinic to see if it would be suitable for his mother. He is still uncertain about committing her there. He calls Bill to inform him about this, and Bill says he will send as much money as he can. He tells Monk that he sees his children only one weekend a month. Monk decides to tell Bill that their father had an affair with a British nurse in Korea and that they have a half-sister. Bill says he cannot deal with this information, but he also wonders whether their father left any more clues in that box.

Monk runs into Lorraine and Maynard on the dock. They announce they are getting married, and Maynard asks Monk to be their best man.

Then, Monk recalls the time he spent with his family on Christmas break when he was in his freshman year.