The nuptials prompt rare moments of frankness from the Roys amidst their usual chaos and scheming.

Love is in the air on this week’s episode of Successionas Lady Caroline Collingwood (Harriet Walter) summons her children and ex-husband Logan (Brian Cox) to the rolling hills of Tuscany for her nuptials with “seat sniffer” Peter Munion (Pip Torrens). There’s an awkward wedding proposal, blistering parent/child reunions, and the dick pic to end all dick pics. Meanwhile, Waystar has a business romance to manage: their deal with Lukas Matsson (Alexander Skarsgård) hangs by a delicate thread in “Chiantishire,” the penultimate episode of Succession’s third season.

Before the wedding, the Waystar board gathers. Kerri (Zoe Winters) intercepts Stewy (Arian Moayed) and Sandi (Hope Davis) to meet with Logan before the meeting proper. Waystar’s inner circle—Tom (Matthew Macfadyen), Roman (Kieran Culkin), Gerri (J. Smith-Cameron), and Logan inform Stewy and Sandi that they’re in the early stages of buying streaming platform GoJo to bolster their own StarGo. Stewy and Sandi feel ambushed, but in the end, they agree to not kill the deal.

The meeting proceeds with Shiv (Sarah Snook) and Kendall (Jeremy Strong) calling in remotely while Logan watches with a careful eye from the glass outside. With one uncomfortable meeting down, the Roys climb into their PJs (having managed to find a way around that condition of the Stewy/Sandi deal) and jet off to Italy.

Kendall, sporting a fresh buzz cut, arrives in Tuscany with his children and Comfry (Dasha Nekrasova) in tow. He’s greeted by Caroline, who informs him that due to his father’s attendance, Kendall may be asked to leave certain events to avoid any unwanted drama.

An icy reunion in the warm Tuscan sun may not have been what Kendall wanted, but should it be any less expected? In season two, Kendall attempted to bare his soul to Caroline about the car accident; she ended up leaving the next day to avoid the emotional conversation with her son. But Kendall’s got other things to worry about besides his mother, like a true-crime doc that, according to Comfry, focuses on “Curse of the Roys,” hinting that the car accident will be featured.

Connor (Alan Ruck) and Willa (Justine Lupe) glide into the Tuscan estate, Connor worrying about a Politico reporter who’s asking detailed questions about Willa’s past. To legitimize their relationship (aka Connor’s bid for presidency), Connor classically misreads the situation and proposes to Willa in front of guests at his stepmother’s wedding reception. Willa hesitates, says yes, and then immediately asks Connor if she “can have a little think” before giving a definite answer. Not wanting to let down the guests, Connor smiles, nods, and says through his teeth that he’s going to act as though she said yes.

At the other end of the estate, the Roy inner circle notices bizarre tweets from Matsson. He’s headed to Macau, with the only clue towards the meaning of his trip a Tweet of videogame controller and the fingers crossed and eggplant emojis. Is Matsson bailing on their deal? Or as Tom suggests, is he just hoping to fuck a videogame? Gerri suggests Roman try to meet Matsson and secure the deal. Roman may listen to Gerri when it comes to business, but as for his habit of sending unsolicited dick pics to her, it’s an open question if that will cease this weekend.

An icy reunion in the warm Tuscan sun may not have been what Kendall wanted, but should it be any less expected?

It wouldn’t be a wedding weekend without a bachelorette party, so the ladies head into the city center to get their party on. Shiv finds Caroline on the terrace. They give a heart-to-heart their best attempt and end up lashing out at each other verbally.

Shiv calls her mother out on giving up on the kids, as she gave Logan custody. Caroline says she was acting in her children’s best interests, as under Logan’s custody they’d retain shares of the company. She twists the knife further by revealing she believes she never should have had kids, and that she thinks Shiv’s doing right by not falling into the trap of motherhood.

Kendall may have struck out with his mother, but he agrees to get Logan to join him for a one-on-one dinner. Kendall lays it all out – he has nothing, and he is nothing without the family and the company. He wants the buyout and a chunky asset, and he’ll go away. Logan says he needs to think about it.

Shiv seems to be back in her element, and back to her old ways of talking a big game without considering Tom’s place in all of it.

Like any kid who doesn’t get what he wants, Kendall lashes out, denouncing Logan as an evil man, and that declaring he wants out because he doesn’t want to be like his father. Logan reminds Kendall of the car accident and leaves him with these parting words: “You’re my son. I did my best. And whenever you fucked it up, I cleaned up your shit. And I’m a bad person? Fuck off, kiddo.”

After the bachelor/bachelorette party, Shiv and Tom reunite. Shiv greets him with a kiss and proposes they have a baby. She follows up by rattling off potential plans for taking over Waystar when Roman inevitably fails.

Shiv seems to be back in her element, and back to her old ways of talking a big game without considering Tom’s place in all of it. Regardless, they get into some “spicy” pillow talk, starting with Shiv saying “You’re not good enough for me. … I’m way out of your fucking league. … But that’s why you want me.” It’s the most honest Tom and Shiv have been with each other this season, even if they won’t admit it the morning after.

As for Waystar’s romance with Matsson, Roman breaks the news to Gerri that Matsson is looking for a merger, not a buyout. It’s not the outcome they were hoping for, but Gerri suggests Roman pitch it to Logan. Roman pitches and lands the deal with a flourish. Gerri texts Roman to congratulate him. Roman being Roman, crafts a text to Gerri with a very vivid dick pick, but accidentally sends it to his father instead of Gerri.

There’ve been a host of tense moments on Succession, but this stands as one of the most nail-biting. Logan declares that he needs five minutes and takes the matter up with Shiv in another room. Shiv uses the opportunity to get one up on both Roman and Gerri, suggesting the latter bring the former’s behavior to the board. It’s a sad moment for Gerri/Roman stans—their relationship may be well and truly dead after this.

With his family out on business, Kendall lies adrift on a mat in the Tuscan estate’s swimming pool, beer in hand. His children announce they’re going inside, leaving their very inebriated dad alone. “Chiantishire” closes on Kendall dropping his beer as his head slowly dips into the water, drifting dangerously off to sleep. Kendall has played with martyr imagery on Succession this season—indeed, he wanted to crucify himself for his birthday. Alas for him, he’s proven unable to live the life of a martyr. With one episode left this season, we’ll have to wait for next week to see if Kendall Roy’s drifting off into oblivion is his final bow.

Episode Superlatives and Finale Predictions:

• Most Iconic Line: Logan telling Kendall during their tense dinner “Not everyone can live this life.” Is this hinting at Kendall’s fate? Or just stating the fact that many will never reach their one-percenter lifestyle?
  
  
• Episode MVP: Caroline, played to perfection by Harriet Walter. She brought depth to Kendall, Shiv, and Roman’s icy mother. She tells Shiv she should have had dogs instead of children, but she could never as Logan “Never saw anything he loved that he didn’t want to kick it, just to see if it would still come back.”
   
• Cringiest Moment: This week’s moment of cringe goes to King of Cringe Roman accidentally sending a dick pic to his dad that was clearly meant for Gerri.
   
• Predictions: The easy route would be to kill Kendall and pin all of the Waystar crimes on him. But when has Succession taken the easy route? Kendall’s gonna pull through, and perhaps even get back into the good graces of Logan. And while the previous episode hinted that the DOJ’s investigation is slowing down, there’s still one episode left for the rug to be pulled out from under the Roys.