Toby has a conversation with Jack’s urn, telling the late Pearson patriarch he wishes he could’ve had his blessing before marrying his daughter and expressing his reluctance to treat marriage so nonchalantly. He knows Kate loves weddings and makes sure to note that he, like Jack, is a king of big romantic gestures. “My BS meter is going off too with this whole courthouse thing,” he says while Judge Judy plays in the background. “I don’t think that this is what she wants to do.” So what does Toby do? Pull off a grand romantic gesture, of course. In an elaborate sweatshirt-removing proposal, Toby spells out “Will you marry me?” (The question mark gets its own article of clothing.) ”You deserve to walk down the aisle between your two stupidly handsome brothers and feel them love the crap out of you,” he says. He formally proposes, and, in happy tears, Kate accepts. Bets on season 2 ending with a wedding?
The briefest stories of “The Most Disappointed Man” take place in the past, and they cover such complicated social terrain in such brief increments that it makes for strange viewing. On one side, we have Rebecca and Jack in the courtroom. The kids are now nearly a year old, and their path to officially adopting Randall is stalled by Judge Bradley (played by Delroy Lindo). Bradley doesn’t give a reason beyond expressing some concerns, but when Jack and Rebecca corner him in the courthouse, he allows them to discuss the matter in his chambers.
Bradley gives the couple a blunt opinion: He says Randall should grow up with a black family. “I never really understood what my blackness meant until a white man called me a n—-r,” he tells them, adding that his father was able to talk him through it “because he understood all the pain that word elicits.” What follows is a powerful monologue about discovering his own black identity and wanting that for Randall.
Rebecca tries arguing their case but fails. Later, she sends him a letter with a family portrait attached, asking him to reconsider. Rather than do so, Bradley recuses himself, and the Pearsons’ new judge, a black woman, Judge Shaw, formally grants the adoption without hesitation. (Head here for executive producer Isaac Aptaker’s take on Randall’s adoption.) It’s rushed and a little bizarre the way such a difficult, nuanced topic is touched on, but only to serve up a joyous milestone for Jack and Rebecca.
The same could be said for the time we spend with William in the episode. While the Pearsons are in court adopting his son, young adult William is nearby pleading guilty and being sentenced to prison. The judge (Sam Anderson) tells him he’s disappointed, given William’s otherwise sterling record, at which point William lays out the state of his life. “Just a year ago, my mother was alive and my girl was alive, and we were having a son,” he says. “Now they’re gone. They’re all gone.” The next day, the judge visits him and grants him a reprieve, telling him he’s going to get him out and get him help. The judge says to remember his face. “If you ever start heading toward the ending I don’t want to write, I want you to picture this ugly old mug,” he says to William, “and make a different choice.”
A brief flash forward indicates that William, as he aged, did just that: He was still surrounded by drugs, only to imagine the judge’s face and avoid them. But when older William — as we met him in the This Is Us pilot — is told his cancer isn’t going to get better and that he doesn’t have much time left, we see him getting read to shoot up. Suddenly, there’s a knock at the door: Randall. It’s the moment they meet in the pilot, when Randall tells William he’s his biological child. We see that Randall, without knowing it, gave his father some moments of happiness he otherwise never would have seen. But William’s struggles with addiction and grief are given the short shrift, so other than giving us some interesting context for where he was at before meeting Randall, there’s not much to get from these scenes.
It’s the moral of Randall’s arc in the episode that brings these many disparate parts together. After arguing over what to do with Beth, Randall decides to visit Shauna himself, and she’s both “everything I thought she’d be and somehow nothing I expected.” Her face is brutally beaten, which she says is why she didn’t want Deja to see her. Shauna tells Randall the story of Lonzo, her ex — not Deja’s father — who sent her down the perilous path to crime and prison. Randall says she still made her own choices; Shauna responds angrily. “You wound up over there because, no doubt, things broke your way,” she tells him. “Don’t you dare say that I’m in here by choice…. Make no mistake, you can give [Deja] your money and you can give her your cheerleading, but I gave her my blood.”
Shauna’s story parallels William’s in the sense that both indicate how circumstances can get in the way of “choices.” It’s something Randall realizes after returning home, where he tells Beth about their conversation. “I think about all those people making choices about my life before I could make choices for myself,” he says to her. Images of Rebecca and Jack holding baby Randall, now officially theirs, flow across the screen, as do images of William, trying to right his life. Randall tells Beth that he gave Shauna their home number — and we end on the sight of Deja, elated, speaking to her mom by phone. Suddenly our two thin story lines fit within the main story of “The Most Disappointed Man.” Both William’s arc and Jack and Rebecca’s story represent This Is Us’ tendency to gloss over complexities and treat subplots like pieces to click into a puzzle — but if that moving final montage reminds us of anything, it’s the the show usually manages to get away with it.