Giles is a beloved character from the iconic TV show Buffy the Vampire Slayer. As the wise librarian and mentor to Buffy and her friends, fans are very invested in Giles’ relationships and love interests throughout the show’s seven season run. In this comprehensive article, we will analyze Giles’ major romantic relationships and prospective love interests to determine who his one true love is.
Jenny Calendar
One of Giles’ earliest and most significant relationships on Buffy the Vampire Slayer is with Jenny Calendar, the computer science teacher at Sunnydale High. Giles and Jenny have great chemistry from their first meeting and eventually start dating in season 1. As their relationship develops, Giles opens up and shows his fun, relaxed side more with Jenny. Their couple name from fans is “Gilenny.”
Giles and Jenny have some ups and downs when it’s revealed that Jenny was secretly sent to Sunnydale to keep an eye on Buffy and Giles. But they are able to move past this betrayal and continue their relationship. In season 2, their relationship gets very serious, with Jenny inviting Giles to her uncle’s wedding. Their love is tragically cut short when Jenny is murdered by Angelus.
Giles is completely heartbroken by Jenny’s shocking death. She is his first major love interest on the show, and her loss continues to affect him deeply through the remainder of the series. Though their time was short, Giles and Jenny had true love, and she leaves a lasting impact as one of Giles’ most significant romances.
Olivia
In season 4 of Buffy, we meet Olivia, an old friend and love interest of Giles who visits from England. Olivia is played by Phina Oruche and appears in 3 episodes. Based on their comfort level and past intimacy, it’s implied that Olivia and Giles were involved long before she comes to Sunnydale.
During her visit in season 4, Olivia and Giles rekindle their physical relationship. Olivia cares for Giles after he is fired by the Watchers Council and helps nurse him back to health. Their connection is strong, but the relationship also has some strain. Olivia expresses concern about the danger and violence in Giles’ life so close to the Hellmouth. She also appears jealous and threatened by his close relationship with Buffy.
By the end of her time in Sunnydale, Olivia seems ready to leave behind the weirdness and complications of Giles’ world. The two care for each other, but their relationship likely worked better when they had distance between them. Olivia returns to England, and we don’t see her again for the remainder of the show’s run.
Joyce Summers
Could Buffy’s mom Joyce Summers have been a romantic interest for Giles? There are a few subtle hints of a connection between them. As single parents of similarly aged teenagers, Giles and Joyce have plenty in common and reason to spend time together. Giles is frequently at the Summers home consulting with Buffy, giving him regular interaction with Joyce.
In season 2, when Spike is threatening Buffy’s family, Giles stays overnight at her house to help protect them. Joyce tells him “the couch is comfy” and thanks him for staying over. Giles replies sincerely, “I wanted to be here.” Could this night have brought them closer together? The warm tone and awkward intimacy of the scene leaves the door open.
Later in season 5, during Buffy’s birthday party, Joyce playfully teases Giles about his rebellious past as “Ripper.” They talk and laugh easily during the party with no romantic undertones. But some fans speculate this may be the start of Joyce viewing Giles differently.
While Giles and Joyce have admiring friendship and a strong bond through Buffy, the show gives very little evidence that they pursue a romantic relationship. Their deep care for each other may contain an unspoken “what if,” but their connection stays within safe parental boundaries.
Potential Interests
Aside from his major love interests, Giles has a few other potential romantic possibilities that are hinted at but never fully developed on the show.
Miss Calendar
In season 1, Jenny Calendar first substitutes for the computer science teacher Mr. Calendar. During this episode, Giles and Miss Calendar have their initial chemistry and start their banter, before beginning to date. If Jenny had remained “Miss Calendar,” she and Giles may have still grown close and gotten together.
Willow Rosenberg
Giles serves as a mentor and father figure to Willow throughout Buffy. But in season 4, Willow makes an offhand comment about Giles having “much older and wiser appeal.” She likely doesn’t mean this seriously, but it raises the question if Willow’s admiration for Giles ever contained a crush-like element.
Buffy Summers
As Giles’ Slayer, Buffy relies on him completely for training and guidance. They have one of the strongest bonds on the show. Buffy sometimes calls Giles “sexy” playfully, and they go to a school dance together. While their relationship stays paternal, if Buffy had pursued romance after she turned 18, Giles may have had trouble resisting his beautiful, once-in-a-generation Slayer.
| Name | Relationship Status |
|---|---|
| Jenny Calendar | Girlfriend (Deceased) |
| Olivia | Old Flame |
| Joyce Summers | Close Friend |
| Miss Calendar | Potential Girlfriend |
| Willow Rosenberg | Student (Potential Crush) |
| Buffy Summers | Slayer (Forbidden Attraction) |
Conclusion
While Giles has a few prospects, his one true love on Buffy the Vampire Slayer is Jenny Calendar. Their connection forms quickly and continues strengthening before tragedy strikes. Giles remains heartbroken long after Jenny’s death, showing how deeply he cared for her. Many fans see Jenny as Giles’ soulmate – the perfect blend of mysterious, alluring, and matching Giles’ inner “Ripper” self.
Olivia, Joyce, and other women hold significance for Giles as well. But none capture his heart completely like Jenny Calendar. Their palpable chemistry and emotionally intimate relationship can’t be matched. Jenny’s shocking and premature death cements her status as Giles’ one real Buffy love interest. Their romance remains his deepest and most meaningful on the show.
As a wise, paternal figure, Giles forms profound bonds with many characters. But the only woman he lets himself fall for and lower his emotional walls with is Jenny. Their connection transforms him. Despite its brevity, Giles and Jenny’s beautiful romance has a lasting impact on fans. When it comes to Giles’ heart, Jenny Calendar is undeniably his one true love.
Giles experiences profound personal growth over Buffy the Vampire Slayer’s seven seasons. He evolves from a strictly professional Watcher to a real father figure for Buffy and the Scoobies. Giles allows himself to love deeply and form a family – an arc often symbolized by his relationship with Jenny. She leaves him stronger and more open-hearted going forward. When considering who Giles’ one true love is, Jenny Calendar still rules his heart.
In summary, while Giles has some other prospects like Olivia and Joyce Summers, his one true love on Buffy the Vampire Slayer is his late girlfriend Jenny Calendar. Though their relationship was cut tragically short, Giles and Jenny had an undeniable connection, intimacy and chemistry that could not be matched. As Giles’ first real love, Jenny leaves an indelible mark and remains the woman who captured Rupert Giles’ heart most completely.