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The first was at university, his classmate, Andrew. They were both training to be Watchers, both hated their destiny. Romances were discouraged but instructors often looked the other way when students got together; the life of a Watcher was a lonely one. Andy knew it was only temporary and so did Rupert. That did lessen the pain when Andy died on a training patrol. His death was the proverbial straw that led Rupert Giles to finally rebel.
And meet Ethan. Looking back, Rupert isn’t certain that what he felt for Ethan was love, but it seemed like it at the time. At the very least it was passion, love bordering on hate and it fuelled his rebellion. Until Eyghon scared him back to the Watcher’s Council. Today, Rupert recognizes it as an odd affection that he harbors for Ethan, one that mellowed with time and distance.
Oz was a surprise, though not an unwelcome one. Bonding over shared musical taste, they’d spend nights listening and lighting up. It should have felt odd, being with a former student, but Oz’s views were laid back and he always made Rupert feel at ease. It was more like being with a contemporary than a former student. Rupert still hears from him, e-mails and postcards. He’s extended an invitation to the castle, sincerely hoping Oz accepts one day.
Rupert had eventually respected Wesley, but never thought of love until it happened. Rupert had to stop in Los Angeles when leaving Sunnydale, for what he thought was the last time. No one knew that his flight had been delayed and that he’d spent the time with Wesley. He’d grown by leaps and bound, Rupert observed. Maudlin reminiscing over beer turned to something more; for one night they found comfort with each other. Rupert thinks of it as a kind of love and mourns the loss of a good man, a good friend.
Of all the people Rupert Giles had loved, he never would have counted Xander among them. Xander was younger and a former student, but looking back Rupert realizes that these objections were silly given two of his previous lovers. Xander wasn’t his type. Xander was annoying. But Rupert had watched him mature, had become close with him, seem him through heartbreak. They understood one another, grieved over mutual friends (and loves). Somehow Xander wormed his way into Rupert’s life, into his bed and eventually into his heart.