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Cal goes on a date with Julie. Julie is not ready to show him her artwork, but they go to dinner. When Julie tells a story about an ex-boyfriend, Cal worries she’ll expect him to talk about his exes and judge his lack of experience. However, she doesn’t continue the ex talk beyond the one story. Cal likes her but questions how to proceed.
Back in the past, after the repeal of prohibition, Lefty turns the Zebra Room into a bar and grill downtown. In the summer of 1944, Tessie Zizmo sits on her daybed, listening to Milton play her a song on his clarinet from his bedroom window across the yard. Milton is now a college student.Desdemona waits in the living room with another Greek couple and their daughter, Gaia. Desdemona has been worried about the attention Milton pays to Tessie, and has started matchmaking to try and avoid more intermarriage. They chat about how lucky it is that Milton has flat feet and won’t be recruited by the Army. Finally, Milton arrives. Gaia’s father comments on his Boy Scout badges. Milton would have been an Eagle Scout if he’d gotten his swimming badge. Desdemona gives Milton a cookie that Gaia made, but Milton declares that he doesn’t like it.
Milton’s not typically attractive, but he makes up for it with confidence. Tessie has all-American good looks. Because of her mother’s exuberance and penchant for scandal, Tessie has become quiet and proper. One day, Milton returns home to see Tessie painting her nails in his house. She’s watching the roast while Desdemona is out. Tessie asks him to play her a song. He places his clarinet against her knee and blows a note. Over the course of weeks, Milton plays the clarinet against different parts of Tessie’s body, increasing their erotic tension.
Desdemona tries to set Tessie up with Michael Antoniou, a seminary student. At Sunday dinners, Milton jealously claims that the church doesn’t want people to think. Michael argues that people need stories and that the church offers the greatest story ever told. Tessie looks on her two suitors as opposites. She thinks about how chaste Michael’s flirtation with her has been and starts rebuffing Milton’s advances. When Michael proposes, she accepts. Milton, angry, joins the Navy, and Lefty reminds him that he can’t swim.
Cal calls Julie up three days after their date and offers a dinner date. When he arrives at her studio, she lets him in to see her artwork, photographs of factories. They kiss.
Now stationed at a naval base in San Diego, Milton is out of his depth. Even training has been dangerous. Despite always wanting to be American, he doesn’t like his American peers, whose talk he considers “knuckleheaded.” During training one night, he overhears two recruits talking about some sort of test that will get them out of drills.
Michael has returned to seminary. Tessie spends her time at the movies. She watches the newsreels closely, hoping to catch sight of Milton. She feels guilty because she knows he joined the Navy because of her.Michael writes Tessie twice a week. She responds to his letters by describing her trips to the theater, but Michael questions why she would go to the movies during a war. After this, Tessie lies in her letters, transforming herself into a virtuous fiancée who volunteers with the Red Cross.
Milton writes letters to Desdemona in terrible Greek. Censors redact much of his letters, but Desdemona can discern Milton’s distress through his shaky penmanship. Milton takes the test for the Naval Officer Academy, pleased to avoid training. Desdemona prays for St. Christopher to protect Milton from the war, promising she’ll send him to fix the church at Bithynios if he lives. Milton gets reassigned to signalman duty. The average life expectancy of a signalman is thirty-eight seconds.
During a newsreel before a film, Tessie sees a sailor who resembles Milton running across the deck of a ship. She admits to herself that she has never wanted to marry Michael and decides she must call off the wedding.
Desdemona and Lefty receive a letter from Milton telling them not to worry, but they realize Milton will likely die in the upcoming invasion of Japan. Desdemona takes to her bed. Tessie tells her she’s going to call off the wedding because she wants to marry Milton. Desdemona, convinced Milton will die, offers her blessing.
However, Milton receives a letter from the Officer’s Academy inviting him to study in Annapolis because of his high score on the exam. Desdemona believes this a miracle from St. Christopher. Milton and Tessie marry, and Michael attends the wedding. Still sad about Tessie, he dances with Zoë.
In the courtship of Tessie and Milton, we see repetitions of patterns in Desdemona and Lefty’s early years, furthering Cal’s emphasis on the circular nature of his family history. Cal has undertaken telling his family story as a self-reflective exercise, a way of understanding himself, and so in analyzing the earlier generations’ patterns, we can learn about Cal’s fears and desires as a character. For example, just as Desdemona doesn’t officially agree to marry Lefty until faced with death, Tessie tries to avoid her feelings for Milton until directly faced with the possibility of him dying. Both women value societal dictates of purity and modesty, and they weigh these above their personal desires unless something shocking and humbling, like death, forces them to confront and acknowledge their true feelings. We also see this tendency in Cal’s sabotaging of his own relationships that he mentions in Chapter 6 and again in Chapter 9 when he immediately assumes doom for his relationship with Julie. Like the women in his family, Cal represses his desires out of a sense of guilt and shame.
These chapters build on the earlier idea that sometimes not being able to be easily categorized is a dangerous and frightening position. Tessie, labeled as a good girl because of her reactionary response to Sourmelina, has a difficult time understanding herself when she pursues Milton instead of Michael. Milton, with his seductive clarinet playing, represents sexuality and promiscuity that she believes she should not want, whereas Michael represents the chaste, virtuous boy that she should want. Tessie’s reluctance to embrace Milton demonstrates a fear not just of impurity but also of what that means for her self-image. She manifests her anxiety around her desires in her letters to Michael that portray her as a nice Greek girl, charitable and hardworking, and trying to transform herself into an idea stereotype. Milton also struggles between two categories: Greek and American. Despite being American by birth, Milton doesn’t feel as American as his Navy peers because of his small stature and intellectual proclivities, which he considers markedly Greek. His not being quite all Greek nor quite all American causes him to feel inadequate and isolated at the base in San Diego. This repeated emphasis on the anxieties of not fitting into a single category foreshadows Cal’s own gender anxieties.
Milton’s stroke of luck in avoiding the war in Chapter 10 furthers the questions the novel raises about fate, free will, and chance. Although Milton’s luck comes shortly after Desdemona’s prayers to St. Christopher, he earns the high score on the officer’s exam himself. However, he only knew about the exam after coincidentally hearing fellow trainees discussing it. Thus, it becomes difficult to discern the origins of Milton’s change of fate. The way Desdemona’s superstition and Milton’s free will blur together brings to mind the way Cal has insisted upon the existence of a genetic fate that, despite its scientific origins, acts in almost a mythical or religious fashion. Just as this paradigm blurs the lines between science and spirituality, Middlesex does not easily separate religion or superstition from the realm of the human and scientific, blurring the binary and drawing attention to how quick the characters are to pin their situations on fate. Again, the murkiness of these distinctions questions how justified Cal’s fatalism is regarding himself. By using genetic destiny to explain his current loneliness and focusing on the patterns in his family as proof, he ignores the variations, whims, chance, and hard work that exist in his family history as well.
In Chapters 9 and 10, Desdemona and Tessie take responsibility for the behaviors of the men in their lives, acting as if they must control the well-being of the entire family. In our first glimpse at Desdemona in Chapter 2, she has a heart palpitation that represents both her inability to control her heart—in this case her attraction to her brother—and also the idea that her body and heart are sick. In other words, Desdemona believes that her impurity doesn’t just affect her silk but also her body. In this sense, Desdemona’s convalescence after Milton’s letter becomes not just grief but guilt, as if her own actions have led Milton to his doom. She takes to her bed, affecting illness, as a physical manifestation of what she believes is her spiritual condition (and foreshadowing a long period of bedrest to come). Tessie acts in a similar fashion by forcing herself to watch the news reels before movies out of guilt for rejecting Milton. Although Michael seems to believe Tessie’s cinema trips are frivolity, her focus on the news about dying soldiers suggests she actually goes both to feel close to Milton and to punish herself through facing what she views as a consequence of her unwanted desires.