Jerry looks to get his massages covered by his health insurance by getting a dentist friend to write him a prescription note for physical therapy. George and Elaine use the same scam but George ends up with a male masseuse, much to his dismay, but the experience makes him question his sexuality. Kramer is convinced that he saw Joe DiMaggio in a donut shop.
George breaks up with his girlfriend, and is brutally honest about the reasons, which causes Jerry problems as she is the IRS agent who happens to be auditing him. Kramer and Elaine have an awkward moment when Kramer starts dating her roommate.
Jerry and Elaine go to Florida to visit Jerry's parents as his dad is being honored by his condo board. Jerry is given an 'astronaut pen' that can write upside down by his dad's neighbour which ends up upsetting everyone.
When a fellow airline passenger is sent to the hospital, Jerry is stuck watching his dog for a few days. With Jerry stuck in his apartment, Elaine and George realize that they have very little to talk about without Jerry there. Meanwhile, Kramer is finding it difficult to break up with his girlfriend.
Jerry is tracked down by the NYC Public Library for a book that he checked out in 1971 and supposedly never returned. George and Jerry reminisce about their high school days when George thinks that the homeless man in front of the library is their old gym teacher while Kramer tries to strike up a relationship with the librarian. Elaine is paranoid that she is getting fired because her boss won't tell her what he thinks of her work.
After purchasing an air-conditioner, the gang is unable to find their car in the parking structure. A series of misadventures ensues, culminating in Kramer actually losing the air conditioning unit.
Jerry tried to help the owner of a small restaurant attract more customers by giving him a suggestion. George is asked by his new girlfriend to take an I.Q. test so he turns to Elaine for help and asks her to take the test in his place. Kramer, meanwhile, tries to hold on to a jacket belonging to his mother's ex-boyfriend as he thinks it helps attract women but the owner comes looking for it.
When Jerry audio records his standup act, he is shocked and intrigued to also hear a suggestive monologue delivered by a mysterious woman. They find out that it was actually Elaine and George, especially, becomes enamoured with her. George is also obsessed with a supposedly new Chinese cure for baldness, which happens to be quite foul smelling. Kramer continues to search for his 'mojo' jacket.
Jerry laments over dating a gorgeous woman who only has her looks going for her. Similarily, George contemplates breaking up with his new girlfriend because she has a big nose. Kramer relays that information so the the woman ends up getting a bad nose job. Meanwhile, Kramer get Elaine involved in his schemes to get back the good luck jacket from his mom's ex-boyfriend.
Jerry and Elaine are left hanging at a boring party after George leaves with one of the female party goers, who also happens to be his co-worker. The host of the party ends up taking Jerry up on his offer to drop by Jerry's apartment when he is in the city and ends up partying with Kramer and an escort at Jerry's place. George ends up paying for his romantic encounter with his co-worker.
Kramer gets a small part in Woody Allen's new film and the gang argues on how he should delive his one line: "These pretzels are making me thirsty." Jerry's car is stolen and the criminal uses his car phone, even answering the phone when Jerry calls it.
When Elaine helps George get a job at her publishing house he buys her a cashmere sweater on sale, due to a small red dot on the sweater, as a thank you gift.
Each one of the gang has a unique experience while riding on the subway, each to different destinations. Jerry falls asleep and wakes up with a fat naked man sitting across from him.
George begins dating a concert pianist but Elaine interrupts one of her concerts when she bursts out laughing at Jerry's pez dispenser. George's girlfriend later recognizes Elaine's laugh and it causes a rift in their relationship where he no longer has 'the upper hand'. Meanwhile, Jerry attends an intervention and Kramer becomes a member of the Polar Bear Club. He also develops an idea for a cologne smelling like the beach.
When Jerry's neighbor goes into a coma after trying to commit suicide, the coma victim's girlfriend hits on Jerry when he comes to the hospital to visit.
Jerry and Elaine set George and Elaine's friend up on a date and, in awaiting the result of the date, promise to keep each other updated with 'full disclosure' details of what each of their friends say about the other. Meanwhile, George begins to worry if 'his boys can swim' after an incident with a faulty condom.
In order to get an extension on his unemployment pay, George makes up a story that he was almost hired by a latex company called Vandalay Industries. When asked for the companies phone number, he gives them Jerry's home number and asks Jerry to answer his phone 'Vandalay Industries' for the next few days.
New York Met Keith Hernandez defends himself against Kramer and Newman's accusations that he once spit on them, using Jerry's 'second spitter' theory. Elaine makes Jerry jealous by dating Keith but when she discovers that he is a smoker, she starts to have second thoughts. Kramer insists that Jerry accompany him to visit a former neighbors baby and George wants to sleep with a very tall woman.
Jerry and George hop in a limo at the airport, pretending to be people that they are not. The limo is scheduled to drive them to Madison Square Gardens so they call Elaine and Kramer to join them, however it turns out that they are on there way to a Neo Nazi convention.
Jerry finds himself attracted to a woman who was a victim of a hit and run accident. He starts dating her, only to find out that she had hit another woman, a woman who Jerry had always wanted to date. Meanwhile, George starts dating one of Elaine's friends and Kramer has a violent physical reaction to the sound of Mary Hart's voice.
George accompanies Jerry to his new girlfriend's art exhibit and feels obligated to buy one of her pieces. Later, Jerry realizes that his girlfriend is a plagiarist when he hears the same words that she wrote to him in an important letter about their relationship, spoken on television. Elaine wears an Orioles baseball cap to the owners box at Yankee Stadium and refuses to take it off and Kramer poses for a painting.
George gets into a confrontation about parking etiquette with Jerry's friend and neighbor Mike when they both vie for the same parallel parking spot- George backing into it and Mike pulling in straight. Elaine borrows Jerry's car and has to come up with a wild story about why it is now making strange noises.
After invading his life one too many times, Jerry revokes Kramer's spare key privileges and and gives the keys to Elaine. This prompts Kramer to reexamine his life and decides to follow his dream of acting and move to Los Angeles. Meanwhile, Jerry needs his spare keys but can't find Elaine so he and George search her apartment and find something unexpected.