- "I have to believe in a better world."
- ―Rupert Giles[src]
- "Giles at sixteen? Less 'Together Guy', more 'Bad-Magic-Hates-the-World-Ticking-Time-Bomb Guy.'"
- ―Buffy, summarizing Giles' rebellious youth[src]
Rupert was born in 1954 into an upper-class family in London, England. His family had worked within the Watchers Council for at least three generations; both his father and grandmother, Edna Giles, were also Watchers, though his great-aunts, Lavinia and Sophie Fairweather, instead used their magical prowess to remain forever young and pursue carefree lives as hedonists. Although as a child Giles dreamed of being either "a fighter pilot or perhaps a green-grocer," being a Watcher was a calling, much as being a Slayer was, and Rupert's father explained his destiny to him when he was ten years old.However, any chance of Rupert having a normal life ended when, as a child, he used the Shard of Stronnos to turn a light demon that was attacking his aunts into a solid form that they could kill, his use of such powerful magic at such a young age confirming his potential, prompting his father to send him immediately to the Watchers Academy where his aunts would have preferred him to have more time as a child before taking on such a responsibility.
In 1972, as part of his Watcher training, Rupert, along with four other Watchers-in-training, was dispatched to the Highgate Cemetery to deal with the mysterious "Highgate Vampire." As it turned out, the Council had sent them out to deal with the threat on faulty intelligence, and the "vampire" turned out to be a Lorophage Demon, a powerful and deadly insectoid demon that fed on the traumatic memories and experiences of humans, driving them insane and killing them in the process. The Lorophage killed the other four Watchers-in-training and began to feed on Rupert, but two elder Watchers, one of them Rupert's own father, arrived and fought the Lorophage off before it could complete the process. Giles lost his innocence that day and his already-tense relationship with his father only worsened. Because of the incident with the Lorophage, Giles chose to turn his back on his destiny and follow his own path.
In 1975, Rupert was a rebellious youth, rejecting his responsibility as a Watcher and dropping out of his attempt at a history degree at Oxford University when he was twenty-one. He delved into dark magics and befriended a group of young people who delved into the dark arts for fun or money: Ethan Rayne, Philip Henry, Dierdre Page, Thomas Sutcliffe, and Randall. Rupert gained the nickname "Ripper" during this time. Together, they summoned a particularly grotesque demon called Eyghon and continued to explore dark magics. While being with his own punk band called Wretched, he ran into his grandmother Edna after many years. She expressed to him her worries over what he had been doing lately and gave him an uplifting speech about choices and redemption. However, this did little to sway Giles and he merely shrugged her off, showing her his Mark of Eyghon. While he briefly fought vampires with her, Edna once again urged him to return to his training as a watcher and all the good qualities he had for this. Again, Giles chose to rebel and remained indifferent to her words.
During this time, Ripper employed tales of demons and dark magics and also claimed to be a founding member of Pink Floyd in order to impress girls, although he later admitted this was untrue. He delved into minor criminal activity, primarily stealing cars, but most likely for joyriding. Following the death of Randall, Ethan and the others failed to exorcise Eyghon, and Rupert accepted his destiny of becoming a Watcher in 1980. His mentor in the Watchers Council was Archie Lassiter.
At some point Giles acquired homes around the south of England, including properties in Bath, Devon and Westbury, in addition to his family home in London.
At the behest of the Watchers Council, Giles traveled to Sunnydale, California, and took up the post of librarian at the local high school. It was unknown why Giles was present in Sunnydale without a Slayer to train. The Harvest was not prevented and Sunnydale is controlled by The Master and the Order of Aurelius. For face the danger, Giles becomes the mentor of the so-called White Hats, a group of vampire hunters. Cordelia inquired about this, but they were interrupted by Xander and Willow before Giles could answer. (Possibly, given Angel's presence there, Buffy was expected to move to Sunnydale before something happened to change Joyce's plans, with Giles being sent there by The Council in preparation for her presence and subsequently remaining.). Having learned about the "real" world from Cordelia Chase—before she was killed—he contacted this reality's Buffy for assistance, but when she left to fight The Master, showing no interest in his theories about how to change the world, he attempted to summon Anyanka, having identified her as the demon who had granted Cordelia's wish that Buffy never came to Sunnydale, in an attempt to restore the timeline to normal. In the subsequent confrontation with Anyanka, she asked him how he could be so sure that the other world was any better than this one. Giles simply replied "Because it has to be" before he smashed Anyanka's pendant, ending the wish and restoring reality to normal, albeit with Anyanka now powerless and mortal.
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