The following version of this book was used to create this study guide: Bushnell, Candace. Sex and the City. New York: The Atlantic Monthly Press, 1996. Kindle Edition.

Sex and the City is a compilation of columns written by Candace Bushnell for the New York Observer in the 1990s that blend journalistic techniques and fictional storytelling. These vignettes offer readers an intimate glimpse into contemporary courtship rituals and modern sexuality, and in the opening chapter, the narrator sets the tone of the book by introducing Charlotte, an English journalist who moved to Manhattan and quickly discovered that love and romance had been replaced by noncommittal sexual encounters and business deals. Contrary to the New York of classic love stories like Breakfast at Tiffany’s and An Affair to Remember, the narrator argues that nowadays nobody has breakfast at Tiffany’s, and nobody has affairs to remember; rather, they have one-night stands that they quickly try to forget. The narrator herself notes that she understands the cynicism of her friends, such as Skipper Johnson and Carrie, and she too had recently decided she does not want to pursue a relationship.

Over the next few chapters, the narrator investigates various dating and sex trends and weaves together anecdotes, interviews, and observations. First, she attends a sex club called Le Trapeze, expecting to find a sensual and exciting experience but instead finding that they hype did not live up to the reality, and that when it comes to sex, there is no place like home. Next, she brings readers into a conversation between four women who find that they have something in common: they have all dated the same man, who they discover is a serial dater. She then discusses the new breed of women in Manhattan: smart, attractive, successful in her career, and still unmarried by her late 30s and early 40s. For the first time in history, women in New York have achieved the level of independence and the ability to travel, shop, work, and remain single, and they revel in it. Next, the narrator investigates the modelizers, a variety of men who prey particularly on young models, and the modelling agents who breed groom girls to go out with them.

Over tea with several friends, including Samantha Jones—a woman admired for her success and singledom—the narrator’s “friend” Carrie decides to give up on love, throttle up on power, and “become a real bitch” and “have sex like men” (42, 45). She then bumps into a man referred to as Mr. Big at two separate parties, and over the next few chapters they start to date. In the meantime, Carrie goes out for lunch with her friend Amalita Amalfi, and through this character the narrator explores the phenomenon of the “international crazy girls” (47). These are women who jet around the globe, adored for their beauty and sexual appeal, date wealthy and aristocratic men, and attend social events in exotic places. But there is another side to the glamour, and Amalita reminds Carrie that unlike her—who, as a journalist, has a career to fall back on—she just wants “to live” and asks, “how many times have I called you, crying, no money, wondering what I was going to do?” (54). Now she has a daughter, no husband, and an expensive and tiring routine of facials, exercise, shopping, and plastic surgery to maintain her appearance.

Next, the narrator investigates the threesome, an arrangement that she demonstrates is nearly always in favor of the man, who simply wants to sleep with two women at once. Then there is the archetype of the Bicycle Boy: a man with a literary profession and a romantic appeal, but in the end, an infantile approach to transportation and dating. Afterwards, a group of city women (34-year-old Carrie, 32-year-old cable executive Miranda, 38-year-old publicist Sarah, and 34-yaer-old banker Belle) visit their recently suburbanized friend who is now married and a mother. Belle is the only married one of the group and all of them are equally repelled by and strangely allured by the big houses, greenery, and domestic life that they discover. After they return to the city, Belle runs away from her husband, Carrie dances topless at a club, Miranda has unprotected sex with a married stranger in a closet, and Sarah rollerblades in her basement at 4am and breaks her ankle. The book then looks at the Hamptons, the getaway spot for Manhattan socialites and party-goers, where life slows down and embarrassing, meaningless sexual encounters occur. Three hopeful bachelors try their hand at finding women to sleep with: 25-year-old pretty lawyer Skipper Johnson who, contrary to everyone else’s opinion, claims he is not gay; 65-year-old five-time-divorced Mr. Marvelous who is attracted to young women; and 37-year-old screenwriter Stanford Blatch, who is gay but prefers straight men. Meanwhile, Carrie spends the weekend with Mr. Big, and their relationship is seemingly developing well.

The narrator then brings readers into a conversation between four young women who met at an Upper East Side restaurant to discuss what it is like to be an extremely beautiful, sought-after, envied, and paid for, all of them under the age of 25 years old. Next, Stanford introduces an underwear model and budding actor named the Bone that he has developed a crush on. Following this, the narrator considers the stories of two men who date women that they really get along with, develop a deep emotional connection with, and have fulfilling sex with, but that they decide not to pursue a long-time relationship with because they are not pretty enough by their standards. Then Carrie meets Cici, a young girl in her 20s who idolizes Carrie for her style and for prioritizing her career over all else. She and her friend Carolyne enjoy tormenting men and attending parties. During a heat wave, Carrie starts spending more nights at Mr. Big’s air-conditioned apartment. Manhattan society starts to crack under the heat and tension and Carrie and Mr. Big argue over their relationship as she realizes she has become too attached. Over the next few chapters, they continue to grow closer, occasionally arguing and Carrie displaying her insecurities and cynicism. She repeatedly debates ending their relationship if he does not make a full commitment to her, but she loses her resolve each time and coasts through the relationship.

The next chapter looks at how mothers in Manhattan go “psycho,” putting all their energy into child-rearing to the point of obsession (157). Then Mr. Big goes away for business and Carrie is lonely. She nearly spends the night with a girl, curious about what it would be like, but at the last minute changes her mind, and the next chapter investigates the figure of the “perennial bachelor,” someone who is in their 50s and still not (and will likely never) get married. Over Christmas, Samantha Jones starts complaining about not having a boyfriend. Skipper also resents how everyone else is coupling up. And Carrie has developed a routine of staying in and cooking dinner for Mr. Big. She thinks back to her difficult early years in the city, and then goes to visit her mother in Connecticut. Next, Bunny Entwistle tells Carrie about her near-marriage to a wealthy and unattractive man. Carrie and Mr. Big then go on a ski trip in Aspen. They fight and she debates ending their relationship yet again, but in the final chapter, she visits Amalita who has again found herself in poverty and as a single mom. The book closes with an epilogue briefly noting the fates of the large cast of characters; for example, Samantha gave up on New York and moved to LA, Stanford’s film was a success, Amalita launched a successful business, the perennial bachelors are still available, and Carrie and Mr. Big are still together.