Dr. Spaceman looks into Liz's mouth as she asks him to examine some cold sores that she gets when she's stressed out. Liz is officially on break after the last TGS show of the season and she's renting a cottage in the Hamptons. As Dr. Spaceman gives Liz a prescription for her cold sores, he asks her why she isn't wearing pants. Liz explains that the "other doctor" told her to take them off. Dr. Spaceman laughs that the "other doctor" is his brother, who's headed off to prison tomorrow for the rest of his life.
Liz visits Jack in his office, greeting him with a pitying tone. Jack tells Liz that he understands that people feel sorry for him because his wife was kidnapped by Kim Jong-Il, but he doesn't want her pity and he's tired of that pitying tone. Jack admits that he misses Avery and all the things they usually do together. Liz tells Jack he needs to try to feel normal again and starts yelling ultra-liberal things at Jack, hoping that by being a "bummer," Jack will feel like his old self. It works! Jack tells Liz to leave. She gives him a double thumbs-up and backs out.
Liz wishes Jenna a good summer. Jenna assures her that she will have a great summer. Jenna reminds Liz about how Jenna performed during halftime at the Wool Bowl. She reports that the sponsors were so happy with her they're naming her the new celebrity Face of Wool, which will be very lucrative.
Liz finds Frank, Toofer, Lutz and John playing Halo in the writers' room. As she talks to Frank, she notices that his character blows up. Liz thinks it means the game is over, but Frank explains that he killed himself because Toofer had him cornered, so now he'll "respawn" and start again. Liz is disgusted that they're killing themselves rather than letting someone else win. Liz can't wait to get out of there. She has a fantasy about Barefoot Contessa Ina Garten being her neighbor at her summer rental. Liz comments that all she has left to do is pay the fine for the bag-in-a-tree incident. She puts the envelope in Cerie's out-box and leaves.
Jenna meets with the National Wool Council in their boardroom. The chairman, Eugene Gremby, informs Jenna that because wool is a "wholesome fabric," there will be a morality clause in her contract. Eugene explains that they're concerned about a certain kind of publicity. He shows her a celebrity gossip magazine photo of Jenna walking Paul on a leash like a dog. Jenna assures Eugene that she and Paul are in a committed relationship. Eugene says they need a few days to think it over. Jenna thinks Eugene just needs to meet Paul and see that their relationship is everything that wool is. Jenna sings to the sheep sitting at the conference table, who nods his approval. Eugene agrees to meet Paul. He'll bring his wife to dinner at Jenna's tomorrow.
Jack finds Kenneth setting up a home-cooked meal in Jack's dining room. Jack doesn't want Kenneth's pity, but Kenneth assures him that he's just helping Jack the way his community back home helps people. They sit down to eat, and Jack comments that he hasn't eaten at the table since Avery's been gone. He points out that Kenneth is sitting in Avery's chair but tells him to stay there because the two of them have similar-shaped buttocks.
Liz sits outside on the porch of her rental cottage as she listens to her Spanish-language tapes. Suddenly, a golf ball shatters a glass table. Too late, Liz hears a voice yell, "Fore!" Tracy comes around a hedge, holding a golf club. Tracy is excited to see Liz, who is shocked. Tracy explains that he bought everything around the house. Tracy asks if Liz minds if Tracy takes a nap on her couch.
Kenneth enters Jack's office. Jack thanks him for dinner the night before and asks if Kenneth can do it again that night. Kenneth would love to, but he has too much work to do because he likes to give everything a good spring-cleaning when the crew is gone. Jack is disappointed.Jenna arrives home to find Paul waiting with an early anniversary present, a new leash she can use to walk him. Jenna explains that, as the new Face of Wool, she has to maintain a certain image in public. Jenna tells Paul that Eugene Gremby and his wife are coming to dinner at their place that night, and they're conservative. She asks Paul to change out of his blouse. Paul isn't happy about it, but he agrees to change and cancel the "sitter" who he's hired to come and sit on them that night.
Kenneth finds Jonathan coming out of the bathroom with a bucket and sponge. Jonathan tells Kenneth that he's made a very dangerous enemy. Kenneth realizes that Jonathan is cleaning and is puzzled because that's his job. Jack approaches and explains that Jonathan "volunteered" to clean up so that Kenneth could come over to Jack's again for dinner. Kenneth comments that it's not just the bathrooms that need cleaning. Jack says that's why Jonathan's family is there, and he'll see Kenneth at seven.
Liz sits in the living room of her rental cottage, holding her head as loud music plays next door. Tracy enters to ask for a cup of sugar. Liz snaps. She wanted to learn Spanish on her vacation, not live next door to Tracy! Tracy comments that he's sorry Liz doesn't want to live next door to a friend. And if they're not friends, that's fine and it won't affect his behavior next season at all. Tracy dumps out a bottle of wine on Liz's stereo. Jack pours Kenneth a glass of wine and stares at him. Kenneth says that he needs to go. Jack tells him not to leave and calls him Avery. Jack has Kenneth put on a pair of Avery's earrings and then sit with him on the couch and talk the way Jack and Avery used to. Kenneth is trapped.
Jenna and Paul, dressed as a man, host Eugene Gremby and his wife for dinner. They make awkward small talk. Eugene comments that he's impressed with how normal the dinner has been and says that it's "very wool!" Just then, the sitter, a little person in a jester's outfit, arrives. Paul pretends that he doesn't know who the sitter is and kicks him out. Eugene applauds Paul and compliments him on his handling of the situation.Back at Jack's place, Jack lies on the couch, sound asleep and spoons Kenneth, who is wide awake. Kenneth tries to sneak away, but Jack hugs him tighter and Kenneth can't move.
Liz returns to the writers' room to find the guys still playing their game. She notices the envelope with her fine still in Cerie's out-box. Liz announces that she came back for the day because Tracy lives next door to her. She can't leave; she can't stay. Liz feels trapped. The guys continue blowing themselves up so that the others can't win, which gives Liz has an idea - she has to blow herself up! Liz tears up the envelope with the fine. Later, Liz appears before a judge and tells him she's not disputing the fine, she's just refusing to pay it. The judge informs Liz that if she doesn't pay, he can sentence her to three weeks of community service. Liz says a number of rude things to the judge to goad him into increasing her sentence to three months, which he does. Liz is thrilled!
Kenneth approaches the breakfast table in Avery's pink silk robe. He asks Jack where his clothes are. But Jack is lost on a tangent of his own self-pity, missing Avery. Jack keeps trying to make Kenneth into Avery. Kenneth has had enough. Kenneth tells Jack that if he wants Kenneth to be Avery, then that's what he'll do, but Avery is mean. Kenneth speaks coldly and forcefully to Jack as Avery. He tells Jack to get over his self-pity and even makes fun of himself. Jack finally gets it. He gives Kenneth back his clothes and tells Sherry to put Liddy in her baby pantsuit because he's taking her to work today.
Jack pushes Liddy in a stroller through Central Park. He encounters Liz, who is in an orange jumpsuit, picking up trash. Liz declares that she got her dream summer - she's outdoors, wearing comfortable clothing, gardening and learning Spanish. In Spanish, a supervisor orders her back to work. Liz responds in Spanish. Jack shares that Liddy just spat up on a white lady's dreads at Strawberry Fields. They're both back to their versions of "normal." Just then, Jenna runs over in a dog suit. Paul approaches wearing a conservative suit and a gimp mask, scolding Jenna. A golf ball hits Paul's head. Tracy walks over with a golf club. As they all coo over Liddy, we see Kenneth spying on them, commenting to himself on the good in them. Kenneth listens to something unseen. He says that he needs more time, begging "Jacob" for more time.
The four guys continue playing Halo in the writers' room, periodically respawning. Liz returns to the writers' room and asks if everyone is ready for Season Six. She realizes that they never left. The guys pause momentarily, wondering how long they've been there, then return to playing their game.