His parents called him "Georgie" and when he was two years old, his family moved to West Texas, where his father sought to make his fortune in the oil business. They first moved to Odessa, and then in 1950 the family made its home in Midland, where George W. Bush spent his formative years. Though political opponents would seek to paint him as an eastern city slicker and an Ivy League elitist, Bush proudly recalled his time as a student at Sam Houston Elementary School in Midland.
One of the most somber periods of George W. Bush's childhood was the time leading up to the death of his younger sister Robin from Leukemia in early 1953. George and Barbara Bush sought advanced medical care for Robin in New York City, while George and his baby brother Jeb were cared for by family friends. After spending seven months in New York, Robin died. When his parents returned home, they took George out of school to break the news to him. According to his mother, he was stunned by the news and repeatedly asked her "why didn't you tell me?", meaning why hadn't they told him that Robin's condition was as serious as it was.
After Robin's death, George H. W. Bush began working longer hours. Barbara Bush's hair had turned white from the stress of dealing with Robin's illness, and George W. took on the role of consoling his mother. Barbara Bush later recalled this period, telling an interviewed, "I must say, George junior saved my life." Friends recalled that he would absent himself from baseball games, telling friends that he had to go home to take care of his mother.
In his memoir, Bush wrote that he "picked up a lot of mother's personality", sharing the same sense of humor and penchant for blunt and direct speech. Bush once said "I have my father's eyes and my mother's mouth." Unlike the elder George Bush, who was driven to be a high achiever, his eldest son grew into a cocky and fun-loving teenager.
In 1959 the family moved to Houston where George H. W. Bush's oil interests were in offshore drilling operations. George W. Bush attended Kincaid, a local private school, before being shipped off to New England to attend Phillips Academy in Andover, Massachusetts, the prominent prep school that his father had attended. He recalled that his friends in Texas saw this as some sort of punishment. Bush himself recalled being unhappy at Phillips. In one anecdote, he was asked to write an essay about a significant emotional experience, and he chose to write about Robin's death. He wrote about the tears he cried and, not wanting to repeat the use of the word "tears", he consulted a Thesaurus before writing "the lacerates ran down my cheek." He received a failing grade and was cruelly criticized by his teacher. It was also the beginning of his reputation for malapropisms.
Bush made it his goal to instill a sense of frivolity into his school experience. He made friends easily and became Andover's lead cheerleader. He organized a stickball league with registration cards that had false ages that could be used as fake IDs in local bars. His grades were not outstanding and the school dean was skeptical of his plans to apply to attend Yale. The dean underestimated the significance of the Bush family's history at the institution.
In his senior year at Yale, Bush became a member of Skull and Bones, the exclusive Yale secret society that both his grandfather and father had belonged to. Before that, he belonged to the Delta Kappa Epsilon fraternity, known as a home for athletes and parties. Bush organized the fraternity's first toga party. He had a reputation for organizing campus pranks. The theft of a Christmas wreath from a local hotel resulted in a charge of disorderly conduct that was later dropped. He was unpopular with some faculty members because of his father's support for Barry Goldwater, who had voted against the 1964 Civil Rights Act. When his father won a seat in Congress and supported the war in Vietnam, this added to George W. Bush's unpopularity among campus liberals. For many years after, Bush harbored a grudge against what he called the "snobs" at Yale and refused to donate to college fund-raising activities.
Bush graduated from Yale in 1968 as the Vietnam War was reaching its peak. The previous spring he had taken a pilot's aptitude test with the Texas National Guard and enlisted in the Guard's 147th Fighter Group. Members of the guard were exempt from assignment to Vietnam unless they volunteered. Other members of the guard at the time included the sons of Governor John Connolly, Senator John Tower and Representative Lloyd Bensen, as well as seven members of the Dallas Cowboys. Bush's admission into the National Guard would become an issue in his subsequent presidential campaign when he ran against Al Gore, who had served in Vietnam.