One early Sunday morning in October 1953, Belle Prater, who lives with her husband, Everett, and son, Woodrow, in an isolated holler in the Appalachians, "vanishe[s] from the face of the earth." Six months later, young Woodrow is sent to live with his mother's parents, Granny and Grandpa Ball, in Coal Station, a small mining town in Virginia. Gypsy Arbutus Leemaster, the daughter of Belle's sister Love, lives next door to the Balls with her mother and stepfather, Porter Dotson. Gypsy is twelve, the same age as Woodrow, and she is excited to become reacquainted with her cousin.
Woodrow, who has grown up in poverty, wears "hillbilly" hand-me-downs and has crossed eyes. In contrast, Gypsy has been blessed with uncommon beauty, and her family enjoys a comparatively solid level of financial security. Gypsy's life seems idyllic, except when "a certain nightmare [comes] to haunt [her]." She can never remember the details of the dream, but it involves something dead, and makes her wake up sobbing and screaming.
After Woodrow arrives, Granny tells Gypsy about their family's history. Gypsy's mother, Love, was very pretty, while her sister, Gypsy's Aunt Belle, was plain-looking, and "couldn't hold on to a boyfriend to save her soul." That changed when Love went away to college; handsome Amos Leemaster came to town and was captivated, for once, by Belle. The two were set to be married, until Love came home and stole Amos's heart away. Amos ended up marrying Love instead, and Belle was devastated. One night, soon after the wedding, Belle went out on the town, dressed "fit to kill." She ran off with Everett Prater, the first man who paid attention to her, and isolated herself from her family up in the holler, where Woodrow was born. About the same time, Gypsy was born to Amos Leemaster and Love. Amos doted on his daughter; he nicknamed her "Beauty," and made her mother promise never to cut her hair. When Gypsy was five, Amos died. Love remarried, but Gypsy resents her mother's new husband, Porter Dotson, whom she feels is trying to take her father's place.
Gypsy and Woodrow establish a comfortable rapport right away after their first meeting. Both children are outgoing and articulate and share a quick wit. Gypsy is appalled by the many small cruelties that her cousin must endure at the hands of insensitive townspeople, because of his crossed eyes and the notoriety of his mother's disappearance. When Gypsy, overcome by curiosity herself, asks Woodrow if he has any idea what happened to his mother, he shares with her a poem that Belle read over and over in the days before her disappearance. The poem describes an open doorsill "where two worlds touch," and admonishes, "you must ask for what you really want."
One night, Granny cooks a special dinner to celebrate Porter's birthday and the family enjoys a comfortable evening of storytelling and camaraderie. Woodrow has never experienced such shared love and closeness, and poignantly declares that if he were allowed to live one day in his life over again, it would be this one. Woodrow wonders how his mama could have left her parents' home, because to him, it seems like a "beautiful place [which] has everything you could ever want, and nothing could ever hurt you [here]." That night, the nightmare that so frequently haunts Gypsy's sleep reoccurs. In her dream, she sees a lifeless form lying in a pool of blood, but she cannot make out its face.
Amos Leemaster built Gypsy a treehouse before he died, and she and Woodrow make it their "secret hideout." One day, while they are sojourning there, Woodrow ponders the line from his mama's poem that reads, "you must ask for what you really want." Woodrow decides that, besides longing for his mama to come back, what he really desires is for his eyes to be straight. What Gypsy wants is to cut her hair short; she feels invisible under her thick tresses, and thinks that if they were gone, people might see what she is really like underneath.
Woodrow describes a mysterious spot in the isolated woods behind the Prater home where "the air is thick and it vibrates." He thinks that this is the "doorsill where two worlds touch" from his mama's poem and concludes that she must have passed through it. Just then, Blind Benny, a local character who wanders the streets at night, passes by, singing a ballad about a mother who tenderly rocks her baby to sleep and then abandons him. As Woodrow and Gypsy listen to the soft strains of the mournful song, Woodrow recalls that his mother used to tell him that she felt as if she was in a straightjacket, being squeezed to death by the circumstances of her life. He concludes that, on the morning that she disappeared, Belle asked "for what [she] really want[ed]"—to get out of her life—and got it.
At school, Woodrow's new sixth-grade classmates all know he is "Belle Prater's boy," and are anxious to meet him, but he immediately sets everyone straight in this regard by declaring, "I don't know what happened to her, and I don't want to talk about it!" Woodrow is kind by nature, and quickly wins the respect of fellow students and teachers alike with his pleasant personality and vivid imagination. Despite his insistence that he does not want to talk about his mother, Gypsy knows that Belle's absence gnaws at him constantly.
Gypsy contracts a severe case of the measles, and while she is confined to her room, Woodrow comes to her window to visit, with Blind Benny in tow. Blind Benny sings to her, and tells her that he and her father Amos "wuz boys together back there in Cold Valley, Kentucky. Later, Porter comes in and solicitously sets up a fan and a radio for his stepdaughter, but Gypsy is irritated by his presence. She asks her mother why she married the man, crying petulantly, "He's not my daddy...I hate him."
When Gypsy is well again, she and Woodrow have a wienie roast with some of their friends from school. Woodrow entertains everyone with stories, but one boy, Buzz Osborne, becomes jealous of the attention he is getting, and gibes cruelly about his crossed eyes. The next day, Gypsy asks Grandpa why "the way a person looks is so important" to others, and the old man sagely observes, "It shouldn't make no difference a'tall...but it does to most folks." He adds that, in reality, appearances do not define people; "it's only what's in the heart that counts." When Gypsy complains that people seem to notice Woodrow's crossed eyes and overlook his goodness, Grandpa says that Woodrow's mother Belle suffered in the same way: she was sensitive and talented, but she only wanted to be pretty like Love. Grandpa remembers that Belle had a gift for piano playing, and notes that Gypsy is a lot like her aunt in this respect. Gypsy thinks that...
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