So far this season, I’ve largely confined Charlie to the notes at the end of my recaps, despite Luke Macfarlane’s solid supporting performance. Compared to season one, when the character’s insecurities about Sylvia and Will’s friendship were front and center, he has been at the margins, mainly offering unheeded advice to Sylvia and practicing for his big Jeopardy! moment. Now that moment is here, though, and Charlie is stepping up.

Given the name of the episode, it’s a bit of a shame that Charlie’s actual time on Jeopardy! is so brief, barring some fan-favorite twist or tournament that could bring him back in the future. The glimpse we get feels as real as you’d hope, with a cameo from Ken Jennings and Johnny Gilbert’s narration. But Charlie chokes, thrown off by some combination of his wife’s lateness and the pressure of finally experiencing something he has pictured for decades. First, it’s a little slipup: His mouth gets ahead of his brain, and he appends the word mode to his Beauty and the Beast answer (well, technically, question). Then he buzzes in but forgets The Bell Jar. Then he drops the buzzer and almost faints. Cue the Weird Al “I Lost on Jeopardy” title sequence.

Anyone who has competed on Survivor or any non-live reality competition knows that being humiliated on-camera doesn’t stop at the end of the taping; there’s typically a period of waiting for the actual show to be televised, and that can be almost as excruciating. In the wake of Charlie’s performance, he can’t stop thinking about it airing on national TV, to the point that he’s researching possible ways to stop it. Apparently, there’s a man in business affairs at King World (the production company that once distributed Jeopardy!) named Ed Little who could kill the episode if he wanted to.

Charlie is clearly going through something here, but Sylvia doesn’t have the patience to listen when he needs it. She’s preoccupied with a high-stress gig planning the annual company party for Charlie’s firm — an event that will double as the retirement party for a founding partner, bringing the guest total to over 1,500 — and Jeopardy! feels trivial by comparison. She should understand how much this means to him, though, after years of obsession and rehearsal. When she suggests they stop talking about the show and “focus on something real,” the flash of hurt in Charlie’s eyes is unmistakable. His return jab about her propensity for quitting feels pretty justified.

Will’s read is correct: Sylvia gets nervous she won’t succeed at each new business venture, so she abandons them. (Ali Rushfield’s script draws a neat contrast between this and Will’s opposite tendency to never quit a job, even when he has every reason to.) But she’s determined to nail this one, even if that means setting aside the safe option — a generic event space with a hideous carpet Stewart likens to “the COVID spike protein” — in favor of something sexier.

Sylvia finds herself agreeing to Stewart’s suggestion of La Cienega Haciendas, an upscale club where the stars hang out. And being Sylvia, she lies about being a member, eventually slipping in on the arm of a guy who mistakes her for being, well, on the clock. This isn’t the type of fiction she can maintain, though, and she does come clean to Stewart. It’s too late, though; he has already gotten approval from the higher-ups, and they want the party here. It’ll blow back on Charlie if La Cienega Haciendas falls through.

“Jeopardy” leaves this thread unresolved, ending on a funny beat (set to Katy Perry’s “Roar”) of Sylvia talking a big game about demanding the manager book their party, only to stroll right past her and out the door. In fact, this is a pretty transitional episode in general, reestablishing stakes and getting back in the swing of day-to-day work high jinks after last week’s bombshell aborted wedding. That means clarifying that Will does intend to keep working at Johnny 66, no matter how much Jenna is pushing him away. And she’s definitely pushing him away: She has already canceled his corporate card, relinquished the company car, and hired some schmuck named Terry (Kyle Mooney) to sit at Will’s desk and do his job.

Despite taking place so soon after the previous episode, this one doesn’t dwell too much on Will’s sadness about the breakup itself. It’s more about what it represents. This is a step backward for someone who is trying to grow up and do things that grown-ups do, like get married and start his own business. We see how much of a regression this is when Will crashes in Sylvia’s ADU and muses about the “shitty little bar” (Jenna’s words) he’d like to open one day. It’s all there in that small, quiet moment when he sits down alone and lets out a “fuck.”

The most memorable material in this episode for once doesn’t involve Rose Byrne. It’s Will and Charlie’s night of bromance, starting with an unexpected bench-press session and continuing at Jay 6, where Will rants at Terry about the corny banner and the presence of hard seltzer at a brewery. He and Charlie take off with some stolen drinks and enjoy them at Will’s old spot, where they have a meaningful conversation about what they each want out of life at this point. Will craves a big swing, most likely the Shitty Little Bar, that will help him achieve long-term stability. Charlie has stability but feels boxed in, especially by the career he has chosen, and wanted Jeopardy! to change his life. The two men make for natural foils.

But a healthy, wholesome chat turns into something else when their tipsy stroll leads them to the home of Ed Little, the man with the power to consign Charlie’s failure to obscurity. Macfarlane gets downright menacing here, to amusing and unsettling effect, as Charlie peers at the property and talks about going back to the way he felt before the show. He rings the doorbell and only backs down from confronting Ed after getting a boost over the wall and trapping himself in an alley behind the house.

The only way out of this is through, literally, and the sequence of Charlie sneaking around and then through the house is surprisingly tense. (It’s also nice to see Will as the relatively reasonable one.) He does manage to get away without the cops being called, only attracting the attention of some stoned kids. But based on Charlie’s behavior throughout the entire episode and his unresolved feelings about what his life has become, this isn’t over yet. Will and Sylvia aren’t the only ones in this cast with some issues to work through.

Inside Jokes

• “Holy shit, it’s Tony Shalhoub. Yo, Monk rules!”

• “I will circle back to you to touch base on the same page.”

• “I think you’ve been fucking with me since the second I came in here.” “No. I haven’t.” Mooney is very funny, and I enjoy the reveal that “Terry” is just a persona the character uses at work.

• According to Katie, La Cienega Haciendas is “so exclusive that it actively does not want you to find it.”

• And in another good Katie moment, she asks if she can “get three back” after attempting to bribe the hostesses.

 It’s too bad Will and Charlie’s night of bromance comes after going through such painful failure.