On a sailboat excursion, tension starts almost immediately when Marla pedantically argues about whether Lila’s signature drink should be called “Vacations in a Cup” or “Vacation in a Cups.” Lila is irritated, and Gary tries to shut the argument down, but Lila turns to Phoebe for an answer because Phoebe is an English professor. Phoebe explains the grammar, then softens the moment by saying language changes according to the people who use it. The group laughs, the mood recovers, and Phoebe is quietly moved by how good it feels to be asked for help and seen by other people again.

As the drinks flow, Marla distracts herself by frantically renewing her car registration from the boat, which annoys Gary and amuses Phoebe. Phoebe and Gary fall into an easy, intimate rhythm of joking about the drink, their fathers, and being orphans, and Phoebe recognizes how rare it has become for her to speak this naturally with someone. Meanwhile, Gary’s father and Marla revisit the family mythology around their celebrated cousin Roy, and Jim tries to entertain and impress everyone with stories, his plane-building hobby, and growing interest in Phoebe.

The emotional center of the trip arrives when Juice asks Phoebe to help hold a funeral for her dead virtual dog, Human Princess. Phoebe asks Juice to say what she loved, then invites others to speak. Jim remembers Wendy buying the toy for Juice, and Gary thanks the dog for keeping his daughter company before becoming overcome with emotion. When Phoebe adds her own thanks, the ritual opens into grief for Harry, for her miscarriage, and for the daughter and family life she imagined but never got to keep, and she briefly sobs in front of everyone.

When it is time to let the dog go, Marla objects that dropping it in the ocean would be littering, and the captain gently asks them to keep belongings on the boat. Phoebe still tells Juice to go ahead, deciding that if she is going to live, she wants to live differently and less fearfully. Juice throws the dog into the water, and the moment passes strangely quickly as the adults return to drinking and wedding chatter, even though Phoebe feels that something real has happened between her and Juice and that Gary feels it too.

Afterward, Lila tries to rejoin the moment by offering Juice an ice cream sandwich, but Juice rejects it, and Gary drifts back to Lila. Phoebe watches Gary and Lila kiss for the crowd and notices that even in affection they seem public-facing rather than private with each other. Juice later throws the unwanted sandwich overboard as well, which restarts Marla’s complaints, but Phoebe stays beside Juice as the girl reads aloud from the inn’s Wikipedia page. By the time they return to the wharf, the others are drunk and cheerful, Juice is leaning against Phoebe, and Phoebe does not want the outing to end because it proves she has stepped back into the world.