Despite slow initial sales, the book became a bestseller. Its characters and events are loosely based on the author's life and his observations on his Greek heritage. Eugenides developed the idea of writing Middlesex after he read the memoir Herculine Barbin, and was unsatisfied with its lack of discussion about hermaphrodites' anatomy and emotions.
The novel begins with the narrator, aged 41, recounting how the recessive gene, 5-alpha-reductase deficiency, caused him to be born with the characteristics of a female. He is christened with a female name Calliope and nicknamed Callie. After learning about the syndrome in his adolescence, he changes his name to the masculine name Cal. The narration periodically returns to the frame story of present-day Cal, who is bearded, male and interested in women, foreshadowing the personal revelations of Callie. The narration briefly explains how Desdemona, Cal's grandmother, predicted her grandchild to be male while Callie's parents had already made preparations for the birth of a daughter.
The story starts again further back in time, in a small village in Asia Minor, with the protagonist's Greek paternal grandparents. Eleutherios "Lefty" Stephanides and Desdemona Stephanides are orphaned siblings who share a close bond that begins to develop into a romantic relationship, despite their misgivings. Soon, in the aftermath of the 1922 war between Greece and Turkey, and amid graphic scenes of the Great Fire of Smyrna, the siblings are forced to seek refuge by emigrating to America. On the eve of their departure, Desdemona agrees to marry her brother. The marriage is possible because no one in America knows they are siblings and, as such, the legal and social prohibitions against marriage between siblings are not a risk. They reach the United States, and settle in Detroit, Michigan, home of their cousin Sourmelina "Lina" Zizmo, hinted to be a closeted lesbian, their American sponsor, and her husband Jimmy. Lefty soon goes into an alcohol-smuggling business run by Jimmy. In time, Desdemona gives birth to a son, Milton, while Lina gives birth to a daughter, Theodora, called "Tessie". Desdemona is made aware of the potential for disease in children due to consanguinity and becomes anxious about her pregnancy and the morality of her sexual relationship with Lefty. With the quality of his marriage declining, Lefty decides to open a bar and gambling room, calling it the Zebra Room.
Lefty and Desdemona's son, Milton, marries Lina's daughter, Tessie. Milton and Tessie, who are second cousins, have two children, Chapter Eleven and Callie. Chapter Eleven (a reference to the fact that he eventually becomes bankrupt) is a biologically "normal" boy, while Callie is intersexed. However, the family does not know this for many years, and Callie is consequently raised as a girl.
At 14, Callie falls in love with her female best friend, who is referred to in the novel as the "Obscure Object" (is a reference to the 1977 film That Obscure Object of Desire directed by Luis Buñuel). Callie has her first sexual experiences with both genders, the Obscure Object and the Obscure Object's brother. After Callie is injured by a tractor, a doctor discovers that Callie is intersexed, and she is taken to a clinic in New York where she undergoes a series of tests and examinations. Faced with the prospect of sex reassignment surgery, Callie runs away and takes the male identity of Cal. Cal hitchhikes cross-country, finally arriving in San Francisco, where he becomes an attraction in a burlesque show.
The club where Cal works is raided by police, and Cal is returned to Chapter Eleven's custody. Desdemona sees Cal as male for the first time, and the book ends when Desdemona confesses to Cal that Lefty was her brother. After learning that Milton had been killed in a car accident, Cal stands in the doorway to the family's Middlesex home (a male-only Greek tradition thought to keep spirits of the dead out of the family home) while Milton's funeral takes place. As an adult, Cal becomes a diplomat and is stationed in Berlin. He meets Julie Kikuchi, a Japanese-American woman with whom he starts a relationship. [1]
[1]. Wikipedia.org
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