By: Quinn Que
Charlie (Luke Macfarlane) is getting ready for work while the kids and Sylvia (Rose Byrne) have breakfast. He’s feeling much better now that he’s attending therapy. Will (Seth Rogen) strolls through the yard with a female one-night stand, drawing curiosity from the children Frances (Sophie Leonard), Simon (Max Matenko), and Maeve (Sophia Kopera) and annoyance from their parents.
Charlie pulls Sylvia aside and, using pointed but carefully phrased therapy language, expresses that he wants Will gone from their property. Sylvia agrees with his request. Charlie then asks her to attend his next therapy session to discuss his life and certain complaints, which she agrees to do despite feeling quietly nervous about the prospect.
Sylvia emphasizes to Will that he needs to vacate the Accessory Dwelling Unit, or ADU, as soon as possible and he agrees. She then asks him whether couples therapy is a good or bad idea, and he tells her it was part of what led to his divorce. When he asks why she’s inquiring, she pretends it’s just casual conversation, though he remains dubious about her motives.
After Sylvia drops off the kids, she, Will, and Katie (Carla Gallo) have a conversation. Diane (Francesca Delbanco), a local realtor who appeared on Katie’s podcast, joins the discussion to say hello. Sylvia strong-arms Will into scheduling a meeting with Diane to review properties immediately, though he worries the realtor will get the wrong impression of him as desperate.
At the first property viewing, Diane mistakes Will for an ex-convict. He corrects her, explaining he’s a brewer looking for a bar location, and she suggests they visit a nearby business space. At the second location, Will is surprised and impressed by what he sees but explains he can’t afford both a new apartment and new business rental. Diane proves very understanding, offering to hold both properties while he considers his options, and they exchange numbers with smiles.
The next morning at the family house, Diane is spotted walking through the backyard past Will’s latest overnight guest. She awkwardly greets Sylvia before making a hasty exit. Charlie and Sylvia are both annoyed, Frances laughs at the situation, and the two younger children don’t understand what’s happening, prompting Sylvia to confront Will.
Sylvia tells Will he can’t sleep with people from “her world” because they’re off-limits and it will make things awkward. He rejects this premise and reminds her that Diane is an adult, though he insists it was a one-time occurrence. However, Sylvia is secretly pleased that Will is rebounding from his breakup and occasionally high-fives his inappropriate puns. Their conversation shifts to her work and the elusive La Cienega Haciendas venue, with Will offering to ask Diane to help book it for Sylvia since Diane is a member.
Will shows up at one of Diane’s open houses, where she assumes he’s obsessed with her. He clarifies he’s just there to ask a favor, and they engage in some passive-aggressive flirtation before he brings up the venue request.
Sylvia successfully books Charlie’s firm’s annual retreat, which is doubling as a retirement party for a founding partner, at the Haciendas, much to Stewart (Guy Branum)’s delight. However, she discovers the chairs for the event were delivered to the wrong address. Will agrees to borrow a box truck and help her retrieve them, and they successfully pick up the furniture.
While stuck in traffic, Charlie’s therapy reminder appears on Sylvia’s phone. She becomes upset that her day ran long and she’ll likely disappoint Charlie, but as she continues complaining about why she can’t attend, Will realizes she’s making excuses. He explains that therapy didn’t actually end his marriage – being in a bad relationship did – and offers to drop her off at Charlie’s appointment.
Will’s truck gets stuck in an alley as they attempt a shortcut. He insists Sylvia take an Uber while he figures out how to escape, and she calls one that’s twenty minutes away. She phones Charlie to apologize for running late and asks if she can FaceTime into the session as a compromise. He begrudgingly agrees, but the app puts a distracting animal filter on her face, causing Charlie to hang up in frustration while the therapist Dr. Melfi (Paul Lieberstein) compliments his assertiveness.
When Sylvia finally arrives, she’s met with subtle hostility and suspicion from both Charlie and the therapist. She insists her lateness was accidental and she’s not hiding anything, but they remain unconvinced. Before they can delve deeper, the session timer expires and Charlie politely agrees to end the appointment.
Charlie and Sylvia hash things out in the therapist’s lobby. She apologizes for not showing up more reliably when he needs her, referencing both today and his Jeopardy appearance. He apologizes for scheduling his session on the same day she was working his firm’s event. The therapist attempts to sneak out for a bicycle ride despite claiming he had another patient, prompting Sylvia to give him passive-aggressive grief for lying.
Will manages to escape the alley and delivers the chairs, allowing the party to start successfully. Sylvia runs the event from her iPad while multitasking, thanking Will, greeting guests, and saying hello to Charlie. Stewart proposes a toast since the event also serves as a retirement party for Frank (Michael Kostroff), a founding partner at the law firm. They play an extremely cringey video sketch set at the office featuring bad acting from Charlie and Stewart centered on Frank, which everyone except Will laughs at out of politeness.
Later, Stewart introduces Sylvia to his best friend “Cabo Carrie” (Aidy Bryant), who needs a new event planner since her previous one just flaked. Sylvia happily accepts the offer for a new client and they agree to meet later. After Sylvia leaves, Stewart and Carrie comment on how jealous they are of her lack of plastic surgery.
Will encounters his ex-wife Audrey (Alisha Wainwright) and they compare notes about their current jobs. Through their conversation, he realizes how much he wants to secure the rental space for his business. He approaches Sylvia, who’s still beaming about her potential new client.
Sylvia, still pleased about tonight’s event and amazed they pulled it off, asks if he’ll help her again with the next assignment. He tentatively agrees to assist her, conditional on her letting him stay in the ADU so he can afford the bar space. She’s nervous about the arrangement but says she’ll discuss it with Charlie, and Will tries to sweeten the deal by promising no more one-night stands, which Sylvia awkwardly smiles at.
Frank gives a farewell speech that receives enthusiastic applause from the happy crowd. At the end, Charlie grabs the microphone and adds that he is also retiring, drawing tepid and mixed reactions. Sylvia appears visibly stunned while Will asks if she knew about this beforehand.
That evening at home, Sylvia and Charlie discuss his surprising announcement. Charlie is excited despite having no idea what his next move will be, no clue about future employment or timing. Sylvia tries to temper her emotions and asks if she can be honest. When he assures her it’s a safe space, she admits she thinks his decision is “reckless and half-baked.” Charlie takes this criticism in stride, smiling and telling her he has “this feeling inside my bones” about the future, as “Can’t Stop the Feeling!” by Justin Timberlake plays in the background.