The New York Public Library notifies Jerry that he owes 20 years of library fines for failing to return a copy of Tropic of Cancer in 1971. Jerry is adamant that he returned the book, vividly remembering that he did so while ogling classmate Sherry Becker. However, he fails to plead his case to Lt. Joe Bookman, the "library investigation officer"—an idealistic, hard-nosed crusader who vows to guard the library system against miscreants, as he makes Jerry out to be.
George recognizes a homeless man outside the library as Mr. Heyman, his high school physical education teacher. After relentlessly bullying George and giving him a failing grade, Heyman was finally fired for ganging up with other boys to give George a wedgie. Needing to confirm whether he ruined Heyman's life, George introduces himself to the homeless man—and receives another wedgie.
Despite scoffing at library patrons, Kramer strikes up a romance with Marion, a librarian, and becomes enamored with her poetry, which moves him to tears. However, her absence from work to visit Kramer and their after-hours rendezvous in the library draw Bookman's wrath.
At Pendant Publishing, after Elaine's regular lunch order is not picked up, she suspects that her job is at risk. Seeing Mr. Lippman's cold reception towards a Christopher Columbus biography recommended by Jerry, Elaine presents Marion's tear-jerking poetry to him, but to no avail.
Jerry reconnects with Sherry to corroborate his story, but her account of events is entirely different, reminding Jerry that he actually returned Tropic of Capricorn with her, having lent Tropic of Cancer to George. Confronted with this, George remembers that he immediately lost the book during the wedgie incident. Jerry duly pays his fine, while the final scene shows the book still in Heyman's possession as he sleeps in an alley.