Giles got to know Jenny Calendar under less-than-promising circumstances. She was helping him with a project to scan the Library's books, and the merging of the printed and the digital didn't go very smoothly. He was clearly uncomfortable around the computers, and she mocked his discomfort, teasing him for being old-fashioned. Neither particularly enjoyed the other's company that day, but the project had one other very unintended side effect: when Willow scanned the contents of a particular tome, she unwittingly freed a demon from the book. Man, I hate it when that happens.

With Moloch the Corruptor running amok on the Internet, Giles realized he needed help from someone who knew computers - namely, the school's computer sciences teacher, Jenny. While he was trying to decide how best to explain to her that there was a demon on the Internet without making her think he was a very crazy person, Miss Calendar shocked him by making his explanation considerably shorter. She already knew. Much to Giles' surprise, Jenny was well aware of the existence of demons. Her assistance was key in solving the problem, and when the danger was past, they took a moment to try and reconcile their differences. She teased him again, but this time her teasing had a distinctly flirtatious tone. Soon after, she became sort of an auxiliary Scooby, providing assistance and support and helping them avert the reopening of the Hellmouth at the end of the season.

When summer break was over, Giles was visibly delighted to see Jenny again. The two began spending more and more time together. Finally, Giles resolved to ask her on a date. He stammered a bit, trying to get the words out, but Jenny was in a hurry to get to class. Whatever he needed to talk to her about, she suggested, they could maybe discuss over dinner? Then go to the school's football game that night? Their first date went well as could be expected on the Hellmouth - a perfectly nice evening went and got interrupted by the need to save some lives, and Jenny playfully asked Rupert how he planned to top that excitement on their next date.

The two continued to grow closer, but a demon from Giles' past came back to haunt him. It possessed Jenny, who had to be put in mortal danger in order for the demon to flee her body. The experience brought their budding relationship to a grinding halt. Jenny still clearly had feelings for Rupert, but she was understandably traumatized by the experience and needed some time.

He tried to approach her a while later, but she was still upset and sent him away. He was clearly hurt, but he understood. Jenny, though, decided that she'd been a little harsh and went after him to apologize. She found him while he was on patrol, but they were rudely interrupted by a vampire. While Giles fought the vampire, Jenny tried to shoot it with a crossbow. Her aim was a little off, though. Instead of hitting the vampire, the arrow caught Giles squarely in the back. He wrenched the arrow out of his back to stake the vampire himself, and he and Jenny hobbled off together. Then the next morning, the sight of Giles and Jenny kissing in the Library showed the Scoobies that the two were once again an item.

Things finally looked great for the couple, so naturally, it was time for disaster to strike. Just before Buffy's birthday, Jenny was approached by her uncle. Both, it turned out, were members of the Gypsy clan that had cursed Angel with the return of his soul. He chastised Jenny for forgetting her mission in Sunnydale, reminding her that she was sent to monitor Angel and make sure that he still suffered for the sins he had committed against their people. She tried to tell her uncle that Angel still felt the weight of his sins and was striving to help people now, but her uncle wasn't interested in atonement or justice. The soul wasn't supposed to help put things right, it was supposed to provide constant punishment. And Angel's growing relationship with Buffy meant that he wasn't suffering enough for what he had done. Jenny was charged with separating the two young lovers.

Jenny tried, but her efforts weren't enough. After Buffy and Angel made love, the vampire's soul was ripped away. In a dream, Angel told Buffy to look to Jenny for an explanation. She confronted Miss Calendar... no, confronted isn't quite the word. She marched into Jenny's class, grabbed her by the throat, slammed her on the desk, and demanded to know what Jenny had done. Giles, who was there, hastily dismissed the class and tried to assure Buffy that she was acting out of grief. However, Jenny admitted that Buffy was partly right. She told them what she knew, insisting that she would have spoken up sooner if she'd had any idea that the consequences of Buffy's relationship with Angel would be so dire. She tried to apologize, but Buffy didn't want to hear it.

Caught between Buffy and Jenny, Giles had to side with his Slayer. Despite their feelings for each other, Jenny had deceived him about her very identity. She tried to make amends and offered to help, but after Buffy turned her back on Jenny, Giles reluctantly did the same.

During Angelus' reign of terror, Giles was clearly miserable without Jenny. Buffy momentarily put aside her anger to tell Jenny that Giles missed her, and Jenny resolved to do what she could to help. When Giles came to give Miss Calendar some news, she told him that she might have some news of her own for him later if he'd be willing to listen. He seemed receptive, and she tried again to explain her actions. She had a duty to her clan and was stuck between a rock and a hard place, she insisted, and when she came to Sunnydale, she'd never expected to fall in love. Giles brightened at her confession, and they agreed to meet at his home that evening. Meanwhile, she stayed at the school to try and find a way to restore Angelus' soul.

Once again, things between Rupert and Jenny appeared to be on the mend. In fact, as Giles came home that evening, the night looked to be full of promise. On his desk were a rose, a chilled bottle of champagne, two glasses, and a note telling him to look for her upstairs. He picked up the bottle and glasses, romantic music filling the house as he followed a trail of candles and rose petals up to his loft. He found Jenny lying in his bed. Her eyes were open, staring straight at the ceiling. She was dead. Angelus had found her at the school and killed her, preparing Giles' homecoming specifically to break the Watcher's heart. He succeeded.

Giles attacked Angelus that night in a fury of rage and grief. It was a suicide mission, but Giles didn't seem to care as long as one of them didn't walk away from the fight. Buffy arrived in time to save Giles, but his suffering was far from over.

Angelus kidnapped Giles to get information about a demon he wanted to summon. Giles, of course, wasn't being particularly helpful, so the vampire happily resorted to torture. The extent of this torture is unknown, but Angelus was well known as a particularly creative and brutal bastard. Still, Giles didn't break. He stood up to the worst the vampire could dish out (short of firing up a chainsaw), but Dru had worse torture in store for him. She delved into his mind to find the one chink in his armor - his feelings for Jenny. She assumed Miss Calendar's guise to get the information they needed, manipulating Rupert with promises that she would never leave him, that they would finally get to have and feel everything they'd been denied.

Giles' broken fingers mended, but I suspect this violation wounded him far deeper. It took Giles a long time to recover from the loss of Jenny. He had buried too many people during his time as a Watcher, he told Buffy, but Jenny was the first one he'd loved.

Pivotal Episodes:
I Robot, You Jane; When She Was Bad; Some Assembly Required; The Dark Age; Surprise; Innocence; Passion; I Only Have Eyes For You; Becoming II

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