In his youth Rupert 'Ripper' Giles dabbled in the occult, participating in darkmagicin a rebellion against his known fate of becoming a watcher for the Watcher's Council. Eventually recognizing his fate as a watcher, he abandoned his wayward youth and delved into the study of demons, magic, talismans and vampires.
Giles first met his slayer charge Buffy when she moved to Sunnydale, California. Moonlighting as a high school librarian offered Giles the ideal opportunity to train the slayer while maintaining her cover as an average teenage girl. As he grew to know the slayer he grew attached to her like the daughter he never had. Realizing that Buffy was a unique case, Giles was forced to adapt his training routines to keep up with an unpredictable teenage girl.
His love interest, Jenny Calander, an undercover gypsy of the Kaldaresh tribe, was murdered by the evil vampire Angelus. The vampire left Jenny's body artfully displayed in an elaborate setup that drove a grieving Giles to attack his enemy with no hope for survival. Only for the fact that Buffy saved him, Giles would have easily become another victim of Angelus' plot.
After Buffy's school was blown up at her graduation ceremony, Giles found himself no longer the centre of Buffy's training. Deciding to open up an occult shop that would allow him to keep the magical items he needed without the inconvenience of having to find another job, Giles employed Xander's lover Anya who had an unusual affinity with money.
At the magical mental breakdown of Willow, Giles offered to mentor her in England to help her control her new found connection with the dark magical powers.
Giles was key in organizing the potential slayers into a cohesive group, opting to bring the fledgling girls to Sunnydale under the protection of the slayer.
This quirky ex-demon supported Giles when he opened a magic shop in Sunnydale. Her straightforward bluntness might have caused tension but her knowledge of all things magical and demonic was second to none.
As the slayer, Buffy was entrusted into Giles' care when she started high school. Providing guidance and training, Giles acted as a mentor and father figure, a relationship of mutual respect developing over the years.
Bright and Intelligent, this fledgling witch looked up to Giles in her formative years, relying on his guidance in matters pertaining to magic and the occult.
An average, somewhat bothersome teenage friend to Willow and Buffy, Xander caused many a problem for the watcher. Trying to find ways to see that he stayed out of the way and didn't die provided Giles many more hours of work than he would have liked.
As Angel the vampire rubbed Giles the wrong way, his undead status instantly at odds with Giles' training.
As Angelus he tortured Giles for fun, reveling in the pain and torment he caused. Using Drucilla to bewitch Giles into thinking his dead lover was really alive, Angelus basked in the abject horror Giles felt at the realization of his deception.
This rebellious slayer rejected his offer of guidance, choosing to take her own path. Lying to save her own skin, Faith attempted to play Giles against Buffy, succeeding only in alienating both her fellow slayer and potential guardian.
A vampire who rubbed Giles the wrong way, Spike was more trouble for Giles than he would have liked. Were it not for his promise to Buffy, Spike would have been staked many times over.