Giles and Jenny met some time in the first season. Ms. Calendar was the sexy techno pagan and computer teacher which was the opposite of Giles who was the stuffy librarian. ( no offense, but before he started to have the secret past and stuff, he was pretty stuffy.) Anyway, all of a sudden their fighting became some major flirting and suddenly, they were perfect for each other. their first date took place in the second season, second episode "Some Assembly Required". After that they were an item until the demon that Giles had summoned while he was younger came back and took over Jenny's body. It almost killed her and she told Giles that she wanted some time away from him. I think that their first kiss took place in that same episode "The Dark Ages". Finally, after Giles tried talking to her, Jenny decided to forgive Giles.
Unfortunately, he was on watch at the time and he was attacked. Using the cross bow that Giles had in his bag, she shot but ended up hitting Giles instead. Then, they were back together. In the episode "Innocence", Giles found out that Ms. Calendar had been sent to Sunnydale to watch Angel and to make sure that the curse still made him suffer and got mad at her for betraying them and not telling them who she was. Once again, they were no longer a couple and in "Passion" Giles and Jenny had decided to meet later that night. But before that could happen, Angel came in after Jenny had just finished her curse to restore his soul. Angel chased her around the school until he finally killed her. Now Giles has no relationship with Jenny and can only wish that they had spent more time together while she was alive.
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