Liz Lemon is visiting Dr. Spaceman to treat some stress-related cold sores. He assures her that there’s nothing to be embarrassed about (he gets them from hookers all the time) and offers her some R&R (Rum and Ritalin) for the stress. However, Liz only wants to treat the cold sores. She feels her stress is under control now that she’s booked a house in the Hamptons for the summe break.
Meanwhile, the others are making their summer plans. Jack is trying to figure out what to do with himself now that his wife has been kidnapped by North Koreans, the writers are engaged in a final melee battle on their PlayStation, and Jenna is about to land a big advertising deal with the Wool Council, who she impressed with a previous performance at the Wool Bowl.
Liz pays a fine she owes to the city for a hate crime she committed against a Jewish tree, and then heads for the Hamptons. Once there, all is going according to plan, until Tracy shows up and reveals that he’s purchased the homes around Liz’s guest house and is treating it like his own private playground.
Tired from a long day of golf, Tracy decides to take a nap on Liz’s porch. He has to rest up for his big night of firing guns into the air. Before he nods off, he mentions that he and Liz will be seeing each other a lot over the summer. He also warns her that he tends to scream in his sleep, but that she should not wake him no matter what, or he will attack.
Back in New York, Jenna is about to finalize her deal with the Wool Council, when the subject of her personal life brings the meeting to a halt. They are concerned that her cross-dressing boyfriend will sully wool’s conservative image. But after a stirring song, the head of the council agrees to give Paul a chance, and sets up a double date with Jenna.
Meanwhile, Jack is copping with the loss of his wife by replacing her with Kenneth. What starts as a simple act of kindness turns into an obsession when Jack forces him, the hapless page, to come over for dinner night after night. Jack’s assistant, Jonathan, ends up getting stuck with Kenneth’s duties, and is forced to call in his family for help.
Later, Liz confronts Tracy about his behavior, and tells him that she doesn’t want him to ruin her relaxing summer. But when Tracy threatens to cause trouble on set next season, Liz is forced to back down.
Jenna and Paul are hosting the president of the Wool Council and his wife. Although it is hard for Paul to hide who he is, the meal is going well. But when Jenna’s “sitter” shows up (a dwarf the couple pays to sit on them) he is forced to pretend that sexual fetishes disgust him.
Kenneth is having problems of his own, as Jack is now forcing him to completely take on the role of his missing wife.
After being forced to sleep over, Kenneth draws the line, and while impersonating Jack’s wife, tells him to stop feeling sorry for himself and move on. The speech snaps Jack back to reality, and Kenneth is free to go.
After the dinner with the Wool Council president, Jenna and Paul decide that they must be true to themselves. At the photo shoot, they publicly make out while dressed in drag, Wool Council be damned.
After much deliberation, Liz has a revelation, and decides not to pay her ticket for the hate crime, which results in mandatory community service. She finds the work relaxing, and is even picking up Spanish from some of her fellow trash pickers. Jack happens upon her in the park, just as Jenna and Paul are out for a walk. Tracy, who hit a golf ball onto the back of a truck and refuses to take a mulligan, is also passing through the park as he plays his way back to the Hamptons.
The group stops to admire Jack’s baby, while Kenneth watches from afar via telescope. In a “Lost”-like ending, he screams to an unseen “Jacob” that he “needs more time.” With that, the story ends, to be continued in season six.
What did you think of the way things ended? Is the show still going strong, or has the quality started to drop off?