Giles' Love Connections
- Jenny Calendar (love of his life)- Jenny was the computer science teacher at Sunnydale High School. Giles couldn't really get to grips with technology so when archiving the books in the library called on Jenny's help. They weren't the best of friends instantly. But as they got to know each other better, they grew closer. Jenny turned out to be a techno-pagan, and so wasn't surprised when strange things went on in Sunnydale, especially to do with Buffy. Eventually Giles and Jenny went out on their first date, but didn't go to plan, but their second one did. They were happy together, until Jenny found out the hard way of some of the darker routes of Giles' past and the things that can happen being around him. She backed away, then realized that it was silly, and they got back together. Things were going well until Jenny told Giles that she was in fact not really Jenny, but Janna, from a gypsy tribe. Giles felt totally betrayed. Gradually they were able to get passed this one issue and the closeness of their relationship returned, only to be quashed when Angelus killed Jenny. Jenny was among the people that Giles held most dear to him.
- Joyce Summers (brief affair due to Band Candy)- When Giles and Joyce returned to their teenage years through some band candy, they became close, but as soon as the candy wore off things were back to normal, only slightly more uncomfortable.
- Olivia (short lived long distance romance)- Olivia is an old friend o Giles' from way back; she's visited Sunnydale on a few occasions. They seem very close, but there are still some unknowns about her.