Jerry Seinfeld learns he has a fine on an unreturned library book from 1971, Tropic of Cancer. Jerry is convinced that he did indeed return the book, as he remembers the girl he was with that day, Sherry Becker, and her orange dress which is “burned into his memory”. Jerry must go down to the library to sort it out, and he invites Kramer, who enthusiastically accepts.
When they get to the library, Jerry learns from the librarian (Ashley Gardner), that his ‘case’ has been turned over to the library investigations officer, Mr. Bookman. Eventually George Costanza arrives at the library, and he’s very upset, claiming that the homeless man on the steps outside the library is none other than Mr. Heyman, a physical education teacher at Jerry and George’s high school, John F. Kennedy High School. Jerry explains to Kramer how George was responsible for getting Heyman fired. As Jerry and George depart, Kramer stays behind and starts chatting with the librarian, Marion.
Meanwhile, Elaine Benes is concerned when a co-worker forgets to ask her what she wants for lunch, and it sets her to worry that Mr. Lippman is planning to fire her.
The following day Jerry, George, and Elaine meet at Monk’s Cafe, where George tells Elaine the story of why Heyman was really fired. Flashing back to the old high school locker room, Heyman and some of the high school boys give George a wedgie, all the while Heyman deliberately mispronouncing George Costanza’s name as “Can’t-Stand-Ya”. As the flashback ends, George confesses that he complained about the incident, and Heyman was fired the next day. Kramer arrives at the diner to alert Jerry that the library cop, Mr. Bookman (played by Philip Baker Hall) is waiting for him outside his apartment.
Bookman and Jerry argue in his apartment about whether Jerry returned the book or not. As Bookman leaves Jerry’s, Marion is waiting to enter Kramer’s apartment, and quickly runs in when she sees Bookman. She worries that Bookman will return to the library and find that she is not there, but she finds it hard to leave her new-found love.
Jerry then proceeds to look up old high school girlfriend Sherry Becker. When Jerry meets up with her, he finds that she has gained weight, and he is a little perplexed at her recollection of that day. She remembers that she wore a purple dress, not an orange one as Jerry recalls, and that the book they read to each other was actually Tropic of Capricorn, not Tropic of Cancer. Jerry then remembers that the book he returned to the library was Tropic of Capricorn and he actually loaned Tropic of Cancer to George, and runs out of the diner.
Kramer and Marion are caught by Bookman as the two stroll through the library after hours. Meanwhile, Elaine’s fears of being fired come closer to being realized when she finds out that Mr. Lippman wants to see her in his office. After she sees Kramer crying over Marion’s poetry, she takes some of it, hoping to impress Mr. Lippman with a new literary find.
Meanwhile, George arrives at Jerry’s apartment, and confirms that the man outside of the library was indeed Mr. Heyman and proceeds to tell how he just received an “atomic” wedgie from him on the library steps. Jerry then confronts George about the book, which George then remembers losing after the original high school locker incident with Heyman.
Jerry reluctantly pays Mr. Bookman, who subjects Jerry to another lecture. Elaine confesses that Mr. Lippman did not like Marion’s poetry. The episode ends with Heyman, homeless in an alley way, muttering “Can’t-Stand-Ya, Can’t-Stand-Ya”, the dilapidated long-lost copy of Tropic of Cancer lying next to him.