Being the main character of Jester of the Gremory Clan, Uther has developed many relationships throughout the fanfic.
Main Characters Edit
Maho Gremory Edit
Maho is the woman who reincarnated Uther and the woman he loves. Several people have compared Uther's and Maho's relationship to that of Issei's and Rias'. She often gets jealous when other girls flirt with or tempt him, even saying that Uther belongs only to her. She loves him very much and is willing to do anything with him. In response, Uther will do anything to protect her, as he loves her just as much as she loves him.
After volume 8, their relationship improved to the point where Maho no longer feels any jealous towards the other girls, with her being the person to first take Uther's virginity (something most of the girls were against at first).
Alice Helsing Edit
Uther is very protective of Alice ever since he met her, pitying the her and Asuna's suffering. Uther views Alice as a little sister that he needs to protect and is willing to fight anyone that tries to hurt her.
At first, Uther attempts to block out lecherous of her, believing that he must protect her and tries to think of her as a younger sister. After volume 6, Alice kisses Uther, causing him to see her more as a woman than his younger sister. After that event, she became more bold and daring in their relationship, as it is implied that she gives him a good morning kiss almost every morning.
Alice desires to stay with Uther forever, even if it means becoming one of his peerage, which happens in volume 9 after Uther's, Shuri's and Lucas' high-class promotion when she became Uther's official Bishop.
Asuna Helsing Edit
DIaochan is the second Rook of Maho's peerage. Issei and Rossweisse have a student-teacher relationship, where Rossweisse is shown to be giving advice to Issei on various stuff from Issei's studies in school, training, and even his relationships with the girls. Rossweisse later gained some interest in Issei during Volume 12, where she and the Occult Research Club members all asked Issei out on a date.
In Volume 17, she asks Issei to become her boyfriend due to her grandmother coming to visit, to whom she told that she does have a boyfriend when she actually doesn't. Later on in the volume, they go out on a date to Tokyo which was interrupted by the appearance of Euclid Lucifuge. During the attack on Auros and Agreas, Issei rescues Rossweisse from Euclid, defeating him in the process. By the end of the volume, Rossweisse develops feelings for Issei, even asking him out on a date to a 200 yen shop next time. In Volume 22, under Rias' orders, Rossweisse was transferred to Issei's peerage, becoming his first official Rook.