"Chiantishire"
The Roys are in Chiantishire for Caroline's big Tuscan wedding. Though Roman is concerned about their stepfather-to-be, Matsson's weird tweets causing his stock price to skyrocket become a more urgent issue as it threatens their planned acquisition. Meanwhile, Kendall has been exiled from much of the proceedings because Caroline's social-climbing fiance wants to appease Logan. He demands that Logan meet him for dinner; later that evening, Kendall accepts Logan's buyout offer, but Logan himself is more tentative, reminding Kendall that he is still his son and Logan still cleans up his messes.
Connor tells Willa that journalists are looking into her work background, and proposes to her to ostensibly preserve their image. Greg cozies up with Comfry, but comments from Shiv and Tom spur him into pursuing a young and pretty countess at the wedding. Roman meets with Matsson.
Meanwhile, Shiv is still smarting at Roman sidelining her. After a painful conversation with her mother, she tells Tom she wants a baby. During their intercourse, however, she hits too close to home by telling Tom that she's out of his league and that she doesn't love him. The next day, she muses on freezing their embryos instead.
Before the banker's meeting to discuss the acquisition, Roman tells Logan that Matsson wants a merger, not an acquisition. Logan says it may be worth doing. Gerri congratulates Roman via text, and Roman sends a dick pic in response...except he accidentally sends it to Logan, who is furious.
Back in the villa, Kendall dips his face into the pool water, and keeps exhaling.
Tropes in this episode
- Babies Make Everything Better: Defied by Caroline, who bitterly tells her daughter Shiv that she regrets having children, but Logan wanted them. This conversation causes Shiv (whose marriage is not too healthy either) to rethink Tom's desire for a child and pitches sex with him on that front, but later backtracks and considers freezing their embryos instead.
- The Bad Guy Wins: Lampshaded by a despairing Kendall, who knows he can't compete with his father's mastery of corruption; he outright labels Logan "evil." Defied by Logan, who dismisses the accusation as melodramatic and hypocritical.
- Central Theme: Kicking the dog just to see if it will come back. Shiv is left on the verge of tears by her mother telling her she shouldn't have had kids, and she, in turn, humiliates Tom by saying she doesn't love him as dirty talk. Roman tries to hide the fact that he's not terrified after Logan accidentally receives his dick pic, and when Kendall finally just asks to leave, Logan decides to Yank the Dog's Chain.
- Eating the Eye Candy: Some outdoorsy Tuscans like what they see when Willa and Shiv explore Chiantishire in their flattering dresses.
- Everyone Has Standards:
- Though Roman admits to not being much of a feminist, he pleads with his father to not fire Gerri for receiving dirty pictures from him, since it really wasn't her fault.
- Deconstructed by Logan when Kendall tries to claim that, unlike his father, he has standards about what he'll do to win. Logan bluntly points out that Kendall caused a man's death, fled the scene instead of trying to get help, and got Logan to cover the whole thing up and make it disappear;
- Failed a Spot Check: Roman ends up putting Gerri's career in jeopardy by accidentally texting a dick pic to his father. This results in Roman and Gerri's previous relationship becoming public, which becomes another scandal Waystar has to deal with.
- Foreshadowing: In her conversation with Shiv, Caroline mentions restructuring the divorce agreement with Logan. This becomes important in the finale.
- Hypocrite:
- When Logan confronts Roman about his fling with Gerri, his main concern is the "fucking disgusting" age difference, all while he's having an indiscreet affair with his roughly 50 years younger secretary.
- He's on the giving end to Kendall when the latter tries to claim that unlike Logan he's a good person, however, noting that good people don't recklessly cause the deaths of waiters and then get their wealthy daddy's help to make it all disappear.
- Internal Homage: To the "number one boy" scene, as Logan methodically tortures his son (Kendall finally just wants out, Logan would rather he rattle around the mailroom) before leaving Kendall to cry. And this time, Kendall tries to kill himself.
- Internal Reveal: Logan learns that Roman and Gerri have a weird flirtation going on, something that the viewers have known since the middle of last season.
- Jerkass Has a Point: When Kendall tries to claim the moral high ground by claiming that he's a better person than Logan and ill-equipped to play the game his way, Logan absolutely skewers him by pointing out that it's only thanks to Logan that Kendall is not serving the jail sentence he rightly should be for causing someone's death; Kendall is in his way entirely as corrupt as Logan, he's just more self-deluding.
- Nice Job Breaking It, Hero: Had Roman decided to adhere to Gerri's request to stop sending her pictures of his penis, Logan likely would've never found out about their secret flirtation. But of course, he just had to keep going with it, and even worse, accidentally sends one directly to his father, spelling both problems for him and Gerri.
- "Not So Different" Remark: When Logan meets with his prodigal son Kendall, Kendall defiantly says he's better than his corrupt father. Logan reminds him that Kendall is also corrupt, since Logan covered up that Kendall killed a man.
- Parental Sexuality Squick: Roman is disgusted when his mother preens about her new fiance.
- Suddenly Shouting: Logan's furious summons of Roman get a flinch out of Shiv.
- Tampering with Food and Drink: Logan considers that his son might poison him, and has Kendall's son taste-test the food in front of Kendall as a power move.
- Wham Shot: Roman sending a dick pic to Gerri... only for the camera to show he's accidentally send it to his father, destroying his rising respect from Logan and his future success.
- Would Hurt a Child: Logan calls over Iverson and feeds him some of the meal Kendall had the chef specially prepare. Of course, this isn't that kind of show (or Kendall, at least, isn't that kind of guy), but the point is made regardless.
