Tales of the City (1978) is the first book in the Tales of the City series by American novelist Armistead Maupin, originally serialized in The San Francisco Chronicle.

Plot

Seeking a change in her life, Mary Ann Singleton moves to San Francisco in 1976, soon finding herself living at 28 Barbary Lane. Her life becomes intertwined with those of her varied neighbors and myriad colorful characters.

The novel is a look at San Francisco in the 1970s, exploring "alternative lifestyles" and "underground" culture.

Characters

• Mary Ann Singleton, a prudish naïf from Cleveland, Ohio, who impulsively decides to leave her sheltered life and turn a vacation to San Francisco into a new chapter in her life.
• Anna Madrigal is the landlady of 28 Barbary Lane. Anna fosters a maternal relationship with each of her tenants, perhaps most aggressively with Mona Ramsey. In addition to gently encouraging Mary Ann to develop relationships, she begins an affair with Edgar Halcyon, which is threatened by a dark secret of Anna's that may soon come to light.
• Mona Ramsey is Mary Ann's spacey, bohemian neighbor. Restless and somewhat melancholic, Mona finds herself unemployed after a particularly self-righteous day at the office. She lets her old friend Mouse stay in her apartment after his male lover ends their relationship, but she moves out herself to rekindle a relationship with D'orothea Wilson.
• Michael 'Mouse' Tolliver is Mona's best friend and eventual roommate. Mary Ann seems to become most comfortable with him, perhaps because they are both from more conservative parts of the country. Mouse is a confident, albeit newly-admitted, gay man. He goes to live with Mona after his then-boyfriend ends their relationship, only to begin a new relationship with Jon Fielding, a gynecologist.
• Brian Hawkins is a waiter and ex-lawyer who also lives at 28 Barbary Lane. Considered a womanizer by nearly everyone he knows, he spends much of his time searching nightclubs and taverns for women.
• Norman Neal Williams lives in the rooftop shed at 28 Barbary Lane. A skittish recluse of a man, he is cruelly referred to as Boo Radley by the other tenants. Mary Ann tries to be friendly with him and eventually finds herself beginning a relationship with him. He has some secrets of his own, however, that threaten to change life for Mary Ann and the rest of the tenants at Barbary Lane.
• Jon Fielding is a gynecologist, compared to a Greek god by Mona, and Mouse's boyfriend for a short time. While Jon himself is a down-to-earth and caring man, his main friends are the 'A-Gays,' a group of wealthy, snobbish homosexual men who are judgmental of most everyone, including younger effeminate gay men (who they refer to by the slang term "twinks"), like Mouse.
• DeDe Halcyon Day is a socialite well-known in San Francisco and the daughter of Edgar Halcyon. She is in an unhappy marriage to Beauchamp Day, who treats her with contempt and admonishes her frequently for her 'puffy' appearance. Aware of her husband's infidelity with Mary Ann, DeDe retreats to an exclusive fitness spa and emerges more confident. Her energized reunion with Beauchamp, however, is spoiled when she realizes that an earlier dalliance with the Chinese grocery boy has left her pregnant. She goes to great lengths to conceal the truth, including sleeping with a particularly grimy gossip columnist.
• Beauchamp Day is DeDe's narcissistic and philandering husband. Aside from currying favor with Edgar—his boss and father-in-law—and deprecating his wife, Beauchamp also finds the time to conduct extramarital affairs with both Mary Ann (who is Edgar's secretary) and Jon.
• Edgar Halcyon is the head of Halcyon Communications. He and his wife, Frannie, have become less fond of each other and, when he learns that he is dying, begins an affair with Anna Madrigal. Edgar is protective of his daughter, DeDe, which strains his relationship with Beauchamp, his son-in-law and employee.
• Frannie Halcyon is Edgar's wife and DeDe's mother. She spends most of her day in an oblivious, alcohol-induced haze. She is partial to mai tais.
• D'orothea Wilson is a successful model who comes back to San Francisco to renew her love affair with Mona. Her race provides a comedic twist to the end of the novel.