All high school relationships are wrong

Issei Hyoudou / Relationships

Issei has developed many relationships with the other characters over time, not only in the occult research club, but also within the 3 major factions, and has also attracted the attention of many female protagonists.

Occult Research Club

Rias Gremory

She is the woman Issei reincarnated as a demon after his death, and with whom he falls in love first. When she first summoned him, she treated him as a kind of "special" case, knowing that he had great potential. As time went by, she began to fall in love with him, this was compounded when he saved her from Rizer and viewed her as an individual and not as the next mistress of the Gremory household or just a demon. She gave Issei her first kiss after his fight against Rizer. Rias becomes very jealous when other girls try to flirt with him or try to seduce him and even goes so far as to say that he is only hers all alone. She loves him very much and is ready to do anything with him. In return, Issei is ready to do anything to protect her, because he loves her as much as she loves him.

It should be added that Rias usually sleeps naked next to him. Because of this, she has no problem with him seeing her naked and lets him touch her breasts from time to time.

When they like their derogatory nicknames "Switch Princess" (by Bikou) who was later officially used in Issei's children's television show "Oppai Dragon" and "Crimson Bust Princess" (from Azazel) she hated this. However, she didn't mind if Issei gets his power ups through her breasts, as she wants to be the source of his power.

In Volume 8, Rias and Issei have to pass an exam to show whether he is suitable to be their future husband. Both passed the tests, but Issei had no idea what this matter meant, but he notes that he would like to marry Rias one day.

In Volume 10, Issei got permission from Ria's mother to start his harem to make the other girls around him happy too. At that time he was trying to overcome the trauma he had received from Raynare. This trauma was the reason Issei couldn't believe that the girls around him were actually interested in him. This created tension between him and Rias until he confessed his love to her in front of the whole audience during the Rating Game between her and Saiaorg. He confessed his love to her again in the club room and called her by her name for the first time, whereupon she wept with joy and also confessed her love to him.

She was heartbroken when she heard of Issei's death and was reprimanded by Sairaorg, but she found new hope when she learned that his soul was still alive through the Evil Pieces.

In Volume 17, their relationship has evolved so much that she doesn't find it so bad when he dates other girls. Because she firmly believes that he would still love her even then. At the end of the volume, Issei asked if they could talk casually in their free time, to which she happily replied yes.

In Volume 22, Rias was there to allow Issei to become a high-class demon during the ritual in which she placed the crown on his head, thereby making him a king. The two became engaged after Issei proposed after Rias' graduation ceremony, making her his first bride.

In Volume 25, when they celebrated the victory over Vidar in the Hyoudou residence, the girls (Asia, Xenovia, Irina, Akeno, Kuroka, Koneko, Rossweisse and Rias) wanted Issei to show them his love, what he did and said that all of them are his brides. This statement reveals that he intends to marry all eight of them.

Asia Argento

Issei has been very protective of Asia since he first met her. He has compassion for her as she never had an easy life and was desperate when she was killed by Raynare. Issei sees Asia primarily as a little sister, whom he has to protect for anything in the world, and takes on anyone who wants to hurt her, such as Raynare, Fried or Diodora. When he thought that she was killed by Shalba Beelzebub, his negative emotions were so strong that he activated the Juggernaut Drive and seriously injured and almost killed Shalba in the process.

Issei often has perverse thoughts about her, but tries to suppress them and thinks he has to protect her from everything that includes himself and tries to see her as his little sister. Towards the end of Volume 6, she kisses him, which causes him to see her more as a woman and no longer as a little sister. After this event, she became bolder and bolder in her relationship with him, waking him up with a "good morning kiss" almost every morning. She loves him very much and got tears in her eyes when her love prediction came true. She would like to give birth to Issei's child.

She was heartbroken and devastated when she found out that Issei was dead and even planned to commit suicide just to be with him, even if he would never approve of it. When she found out that his soul was still alive, she began to cry with joy and regained hope. She hugged him when he came back.

Akeno Himejima

When Akeno first saw Issei, she thought he was cute kouhei, that she can pamper and flirt with. However, as time passed, she saw his kindness and compassionate manner towards others and fell in love with him in Volume 4. Even though Issei has great hatred of the Fallen Angels, he never despised Akeno because he only considered them a loving one Senpai sees.

Akeno approaches the relationship much more aggressively than the girls when she flirts with Issei. In Volume 7, she tells him that she loves him after he helped her reconcile with her father. Akeno is not afraid of getting into a fight with the other girls when it comes to Issei, as she loves him as much as the rest. She gets jealous when other girls flirt with him, but on the other hand is more relaxed about it than the others or Rias. She thinks it's OK to only come third in his harem, after Rias and Asia, because she likes the idea of ​​an affair with him.

She was heartbroken when she found out that Issei was dead, she closed herself off from reality and became downright lethargic, she only remembered the time she spent with him and began to cry terribly when her father died to comfort her. They and everyone else regained hope when they learned that Issei's soul was still alive. She hugged him when he got back and asked him never to leave her again. She is psychologically dependent on Issei, as you can see from her behavior when everyone thought he was dead or when she got angry when he lost to Sona Sitri in the rating game. She showed an overwhelming will to kill against Siegfried, whom she found on the roof of Akuja research laboratory, since his group was responsible for Issei's death.

She sometimes loses hers "Onee-sama" Aura when she is around him and starts acting like a girl her age, like in Volume 7 when she was on a date with him. She was depressed when Issei had to play Rossweisse's friend in order to deceive her grandmother in Volume 17. But she was cheered up again by Rias when she told Issei that he would also have to go on a date with her and Akeno when the whole thing with Rossweisse is over. During Milicas' visit to the human world, Akeno said that she would like to have Issei's child one day. Issei knows that Akeno is mentally unstable, so he worries a lot for her and promised not to die again.

Koneko Toujou

First of all, Koneko doesn't like Issei because she didn't like his perverted thoughts and antics. But she learned to respect him when she saw his determination and stubbornness never to give up, and how great his willingness is to help his friends. Even if his methods were rather lustful in nature, his courage was big enough to leave a good impression on her, which spurred her on to become stronger and braver herself.

She develops feelings for him as he helped her overcome her fear of Senjutsu by saying that he was by no means scared of her strength and would stop her whenever she got out of hand. After this incident she sat nowhere else but on his lap and began to seduce Issei like all the other girls in his harem. Like the other girls, she becomes jealous when other girls show some kind of attraction towards him or want to get intimate with him. She always gets angry with him when he suggests he isn't one Lolicon.

After Issei went to Juggernaut Drive and returned to Volume 12, he always has healing sessions with Koneko, which uses Senjutsu to restore his life energy that he lost through the mode. During one of these sessions she stated that she would hate it if he died and that she would do this session until her death if it meant that he didn't use that mode again. She even explained to him that there is a quicker way to cure him, but that it would involve sex, but Issei shyly refuses this method because he wants Koneko to do it with someone she loves (Issei can't yet believe they could mean business with him).

That love grew and grew until it culminated in Volume 11 when, she was hers Mating season reached prematurely and chose him as a partner, but she was stopped by her sister Kuroka. Shortly afterwards, Koneko stops Kuroka from seducing Issei and declares that he is hers. Later in the same volume, she proposed to become his bride, but Issei only accepted this on condition that she still needed to grow in size and chest. She wants to be more than just a friend to him because she chose Issei as her soulmate. She is very serious about her relationship with him, but she has to wait until her body is more mature, as it would be too dangerous for her to give birth at the moment. When Issei died she cried together with Ravel and was happy when she heard that his soul was still alive. When he came back she hugged him.

Yuuto Kiba

Kiba is Rias' first jumper and describes himself as Issei's best friend. Issei is extremely jealous and hostile towards Kiba at the beginning of the series as he gets the attention of all the girls because of his looks. Ultimately, however, both became friends after spending a long time together because of the training and their discussions about their future. Both want to get stronger to protect the girls in the Gremory group. Issei and Kiba have a good friendship with each other and are ready to protect each other from any harm. When Issei died, Kiba felt sadness and anger, but did not let these feelings out. He took out his anger on Siegfried, although he had lost he regained his strength when one of Issei's Evil Pieces turned into Ascalon for him. Like the others, he found new hope when he heard that Issei's soul was still alive.

Kiba also sees him as a strong rival and has noted several times that he wants to fight on the same level as him, or even defeat him.

Irina Shidou

Irina and Issei have been friends since childhood, in Volume 3 they met for the first time in years and Issei was surprised when he saw her because he thought she was a boy. She has been in love with Issei since they were little and was shocked to see that he is now a demon and a pervert. Nonetheless, her feelings for him didn't change. She wants to make love with him and give birth to his children as well as Xenovia to strengthen the troops in heaven. She loves Issei very much, but has trouble expressing her feelings like the other girls, as she threatens to turn into a Fallen Angel if she approaches "impure" Thinks or does things. In Volume 16, it was revealed that she was looking for a way to have sex with a devil without falling. In Volume 18 it was revealed that Michael had created a room in another dimension so that she could sleep with Issei without the risk of falling. It was also revealed that she stole Issei's first kiss when they were kids.

After what happened in Volume 18, when Irina kissed him again, she began to call him "Darling", became more attached to him, learned to cook for him, began to bathe with him and often slept with him. She became more and more relaxed and didn't care too much about falling out of it when she could be more intimate with him. She even offered him sex.

Xenovia Quarta

Xenovia and Issei met in Volume 3 and were not yet interested in each other at the time. Issei initially disliked her as she referred to Asia as a witch and wanted to kill her, but this changed at the end of Volume 3 when she became a demon herself, after which she learned of God's death and apologized to Asia. She then decided that she wanted to have strong children and chose Issei to have them with her. She is very shameless when it comes to sexual matters, even though she grew up in church, she tries to have sex with him everywhere, and even went so far as to bring condoms to school to practice with him there.

She would like to have his genes as the Red Dragon Emperor, as she wishes to have strong children, as a kind of reparation for the time she believed she had lost as a woman because she served God and not out of romantic feelings. This changed when she fell in love with him, as he asked Michael to give her and Asia the opportunity to pray without the aftereffects that a demon would otherwise have. As the series progresses, she develops genuine romantic feelings for him because of his determination to protect his friends, even if it means hurting himself in the process. She always exudes an eerie aura when another girl approaches him.

Xenovia expressed concern the further her relationship with other girls evolved, the more distant her own relationship with him. This made her decide to act more aggressively herself to seduce him, as shown in Volume 16. Despite his difficulty understanding her personality, like all the other girls, he is willing to protect her from harm. Xenovia wants Issei's peerage when he becomes a high-ranking demon, which eventually happened.

Gasper Vladi

When Gasper and Issei first met, he thought he was just another girl and was shocked in the end when he found out that Gasper is a boy in girls' clothes. Issei often curses Gasper because he is such a couch potato, although both are good friends and Issei trains him. Issei's blood gives Gasper a power boost when he drinks it and allows him to briefly gain control of his Sacred Gear, which then allows him a balance breaker. After Issei died, Gasper was filled with anger at the Khaos Brigade who killed his beloved Senpai and friend and defeated Georg with the strength he had developed.

Both have a decent Senpai-Kouhai relationship, as Issei teaches him various things and helps him with difficulties. The two have an extremely good relationship and form a strong team. It also looks like Issei is also teaching him his perverted ideals and Gasper, innocent as he is, admires his senpai in the process. Gasper helped Issei use his dress break twice by freezing his goals in time.


Rossweisse is the second tower in Rias Peerage and a teacher at their school. Issei and Rossweisse have a student-teacher relationship, where she helps him with various school matters, trains with him or gives him advice about girls. In Volume 12, she started showing a little interest in him after the other girls asked him out on a date.

In Volume 17, Issei had to play Rossweiß's friend, because the latter's grandmother came to visit and she told her beforehand that she had one. Later in the same volume, they both went to town on a date, which was cut short after Euclid Lucifuge showed up. During the attack on Auros and Agreas, Issei saves them from Euclid and in the end defeats him. Towards the end of the volume she has developed feelings for him and asks him if he would like to have a date with her in a 200 yen shop the next time.

Ravel Phenex

Ravel and Issei first met in the rating game Rias Vs. Riser and didn't have much to do with each other. Only when he challenges her brother Riser at his engagement party with Rias and defeats him, does she begin to develop feelings for Issei, albeit à la Tsundere at the beginning. In Volume 10 she moves in with him and changes to the Kouh Academy to spend more time with him. She is in the same class as Koneko and Gasper.She said that she had no problem with his own mistress as long as she is allowed to stay by his side. Issei is not aware of her feelings for him, but is ready to sacrifice his life for her because Lady Phenex asked him to take care of her. She was happy when Sirzechs asked her if she would like to become Issei's manager. She works very hard for him, such as finding a suitable magician for him to make a pact with.

Issei respects and admires Ravel for her vast knowledge and dedication as his manager. He trusts her completely when making decisions. Issei stated that he would like her to be his manager forever and as a strategist when he becomes a high-ranking demon and receives his own set of evil pieces.

Student council

Sona Sitri

At first Sona treated Issei like an ordinary servant, but over time she began to admire him for his hairiness and courage. Sona respects him very much for everything he has done so far, but is also jealous because he was able to solve problems for Rias where she was unable to, even though she is her best friend and a high-ranking demon. She later regards him as a boyfriend and Ria's boyfriend and allows him to address her by her first name. She asks Issei to take care of Rias despite her pride and stubbornness. She congratulated him on his promotion to Middle Class Demon.

Tsubaki Shinra

Sona's lady, Issei, knows about her feelings for Kiba and encourages her to get his attention. However, she is afraid that he might be interested in Issei. Tsubaki and Issei email each other regarding Kiba, much to his confusion.

Genshiro Saji

Saji and Issei share a friendly rivalry for each other as both are farmers, both are in love with their master, and both have a dragon in their sacred gear. In the beginning the two didn't have much to do with each other, but as time goes by, both develop a good friendship with each other. In Volume 3 they said they were "Was Buddies " and started to train to face each other. When Issei died, Saji was angry and sad and he wanted to avenge him.

Tsubasa Yura

She congratulated Issei when he became a middle class demon and asked for his autograph. She said that he is exactly her type because he always likes to come back dirty from fights. She admired his fight against Sairaorg. She is in love with Issei.

Fallen angel


Raynare has been a fallen angel. She was Issei's first friend under the pseudonym Yuuma Amano, she tricked and deceived him in order to be able to kill him, as he could represent a possible danger. She killed Issei with a light spear at the end of their date together and also killed Asia when she removed her Sacred Gear Twilight Healing. This was also the reason why Issei began to hate all fallen angels. He later defeated Raynare, whereupon she resumed the form of Yuuma to dissuade him from killing her, but Issei saw through this ruse and asked Rias to put an end to her.

In Volume 10, while Koneko, Asia, and Akeno were healing him, it was explained that even after her death, Raynare left a dark mark on Issei's heart. She caused his fear of women because, after he had planned their first date so carefully, she ended up mocking his feelings, and ultimately killing him too. She even frightened him to the fact that he could not address girls by first name he loved (hence Rias "boss" (English President (Japanese Buchou))). He is also afraid of showing feelings towards the girls, as he is afraid that the girls might reject them or that they will not like him anymore. After being laughed at by Raynare, he set up a mental block that blinded him to the feelings of the girls around him and therefore did not notice them. For example, prior to volume 10, he assumed that Akeno and Rias were only paying him attention because they were looking for him for theirs "cute Kouhei" and kept something like a pet. The girls got behind all of this and lifted the curse that was on his heart. He was then able to recognize the girls' feelings, but sometimes he is still clueless.


Issei initially hated Azazel for being a fallen angel, but later learned that he only meant well and had no bad intentions. He respects him very much and even calls him "Sensei" after he promises to reveal the secrets of the Sacred Gear and how to wrap pretty women around your finger. Azazel becomes the advisor to the Occult Research Club from Volume 4 and helped the Gremory team to fight better as a team. He also helped Kiba and Issei develop their Sacred Gear and helped the latter achieve his Balance Breaker and use the Triana properly. Azazel is deeply concerned about Issei and was upset when he passed away. He was relieved to hear that his soul was still alive.


Baraqiel first hates Issei because he misunderstood the meaning of Oppai Dragon. He thought the Oppai Dragon was a dragon that eats women's breasts and not a dragon that loves breasts. He feared that Issei would want to eat his daughter Akeno's breasts. Since the misunderstanding was cleared up and Issei helped him and Akeno to reconcile, Baraqiel respected him and gave his consent to their relationship.



Issei sees Michael as a powerful leader and respects him for it. Michael also likes Issei and therefore gives him Ascalon as a symbol of peace between the three factions and fulfills his wish that Asia and Xenovia may also pray to God as demons without being harmed.

4 great satans

Sirzechs Lucifer

Sirzechs is Rias' big brother, he first met Issei during Rias engagement party with Riser. He shows great interest in Issei and sees him as part of his family. He also allows him to call him big brother, but Issei believed that this would be impossible because he is a Satan. He showed that he was upset with Issei's death and wanted revenge for him, like all the others. He was also happy when he heard that his soul was still alive. He showed great confidence that Issei's relationship with Rias would continue to develop. Sirzechs later gave Issei his old role of "taking photos of Rias while sleeping", Rias was upset when she found out, but had no problem with Issei doing it, but was very much against Sirzechs doing it.

Serafall Leviathan

There's a bit of a rivalry between Oppai Dragon and her own Magical Girl TV series, but it seems like she gets along with Issei otherwise.

Ajuka Beelzebub

It seems like Ajuka likes Issei, as he was ready to correct the code of his Evil Pieces, which was overwritten because of the Juggernaut Drive, in order to avoid malfunctions in the future and also intentionally gave him cheat-like abilities in rating games. However, whether it is only part of an experiment, a request from Sirzechs or some other reason is not yet known.

Falbium Asmodeus

Falbium is the laziest of the four Satans and leaves most of its duties to its servants, much to Issei's horror. However, in Volume 8 he helped with the trial of Issei and Rias as "Satan Green "

Gremory clan

Zeoticus Gremory

Zeoticus Gremory is Rias' father and first met Issei after his fight with Riser. At first he was disappointed that his daughter did not want to marry into the Phenex family, but later accepted this decision, knowing that she loves Issei. He became very fond of Issei and made good friends with his parents. He sees him as part of his family and wants Issei to call him father. Like his son Sirzechs, he is confident about the relationship between Issei and his daughter. He likes to surprise the two, to which both react embarrassed (especially Rias).

Venelana Gremory

Venelana Gremory is the mother of Rias and, like her husband, was disappointed that her daughter did not want to marry into the Phenex clan. However, she accepted Ria's decision to love Issei and was devoted to him. She accepts him as a member of the Gremory family, she wishes for him Hahaue or Okaa-sama to be called. She trains him in dance and high manners so that he can be a gentleman and not embarrass Rias in social events in the underworld. Issei tends to have perverted thoughts about her because she looks so much like Rias.

Grayfia Lucifuge

Grayfia is Sirzechs 'wife and Rias' sister-in-law. She first met Issei when she stopped Rias before she could sleep with Issei to break her engagement to Riser. She was there when the Occult Research Club suffered a loss to Riser in the Rating Game and helped Issei win Rias back and break her engagement. It turns out that she is very concerned about Rias, but she accepts Issei as her friend. Like the rest of the family, she seems to be very fond of Issei. Volume 12 showed that she was one of the few who didn't even consider the possibility that Issei might be dead. She said "that her future brother-in-law would never die from something like Samael's curse". At the onsen in Izu, she was happy that he would be part of the family and, much to his surprise, washed his back. She sees Issei as her little brother. She challenges him to her "Ane" to be called, just as Sirzechs insisted on him "Onii" should call.

Millica's Gremory

Like his father, he likes and respects Issei very much and calls him "Issei nii-sama". When Sirzechs asked him who he liked more Oppai Dragon or Satan Red said this very much to the shock of his father Oppai Dragon. Millicas and Issei share a brotherly bond, he asks him if he would address him by his name without any additions, since he had felt lonely when Issei spoke to Rias without any and was happy when he did the same with him.

Phenex clan

Lady Phenex

She is the mother of Ruval, Ravel and Riser. Issei first met her in Volume 10, he initially thought that she harbored a grudge against him for breaking the engagement. However, it turned out that the people of the Phenex clan are all warm-hearted. She asked Issei if he could take care of Ravel and keep the bugs (boys) at bay. With the knowledge that Ravel loves him and only wants to be of use to him, as one of his lovers.

Riser Phenex

At first Issei hates Riser because he tried to take Rias away from the whole group. At the end of the Riser Vs. Rias Peerage fight, which was about who to marry, Issei stormed up to him and was almost beaten to death because he was at the end of his strength until Rias intervened. After he only woke up after two days, he stormed to their engagement party to prevent it, Sirzechs suggested that they do it with one One on one fight to decide. Issei previously gave up his left arm in order to reach the balance breaker of his Boosted Gear for a very short time. Issei only had ten seconds to win against him and used a strategy / backup plan if his Balance breaker would end before he beat Riser. After this fight Riser became depressed because he had never lost before and developed a great fear of dragons. Later, during the invasion of the underworld, he went to battle the monsters after overcoming his fear through Tannin's training organized by Issei and Ravel. He tried to help his sister cope with Issei's death. Issei didn't really hate him anymore when he won Rias back, they both often talk to each other via the magic circle, but Riser is jealous of Issei because he now has Rias and would like to have a rematch at some point.


One of Riser's Towers, Issei defeated her in battle from her masters with Dress Break and Dragon Shot. Isabela respects Issei's strength and said that if he got stronger then she would have more to brag about in her stories.


One of Riser's farmers, she originally hated Issei for his perverted nature and because he was Dress break had used in battle by their masters. However, she later became a big fan of his and even asked for an autograph.

Bael clan

Sairaorg Bael

Sairaorg is Ria's cousin, Issei first met him when it was decided which of the young demons will compete against each other in the rating game. He is known as the strongest young demon. Both wanted to fight against each other and did so shortly before their actual match, in which Issei found out that Sairaorg is very strong and Issei found him interesting.

During the Rating Games Sairaorg Vs. Rias he immediately got involved in a fistfight with Issei. Issei later found out that Sairaorg's farmer Regulus is actually a Sacred Gear and united with him to activate the Balance Breaker. The fight ended with Sairaorg knocked out while standing. After the match, they both became good friends and vowed to get stronger and fight each other one more time. When Issei died he came to cheer Rias up and didn’t believe that he was dead because he couldn’t have sex with the woman he loved.

Astaroth clan

Diodora Astaroth

Issei hated Diodora the first time they met, because he tried to take Asia away. Diodora, on the other hand, looked down on him, calling him a "dirty dragon" and just touching him made him sick. Issei's hatred was later heightened when he learned that Diodora had planned that with Asia in advance, that if she healed him, that she would be kicked out of the church as a heretic. Then he wanted to add them to his "collection".

Belial clan

Diehauser Belial

Issei admired and respected Diehauser for being first in the rating game. In Volume 20 he was disappointed when he discovered he was a traitor and tried desperately to keep him from publishing the corruption of the Rating Game. Because this would only have caused unrest and chaos. When Dielhauser discovered his real intentions, Issei began to respect him again.

Team Vali

Vali Lucifer

Vali is Issei's rival and the owner of the LonginusDivine Dividing. When Vali and Issei met for the first time, Vali was on a completely different level than he was, which prompts Issei to train more. During the signing of the peace treaty of the three factions, he turned away from everyone and started his own team in the Khaos Brigade. This provoked hatred in Issei and he fought against Vali in the Balance Breaker, which he could reach through Azazel's bracelet. Issei won the fight as Vali was teleported away. Later they both joined forces to fight Loki to defeat him and then they began to work together. They both started becoming friends later in the series, but the rivalry persisted. They later vowed that one day they would fight each other and get even stronger.


Kuroka is Koneko's big sister, Issei first met her in Volume 5 when she tried to kidnap her little sister and was just stopped by him and Rias. He fought for Koneko, almost slapping her in the face. He warned Kuroka that if she tried again, that fist wouldn't stop. While Konekos "Mating Season " she made matters a little worse when she stimulated both Koneko and Issei. In the end she stopped her sister from doing so, but tried to sleep with Issei herself in order to produce strong offspring, as Vali had already refused. Then it was stopped again by Koneko. When Issei found out more about her past, he told Koneko that she was a good person, even if she was and remains an "indecent cat". She feels drawn to Issei and later develops strong romantic feelings for him.

Le Fay Pendragon

Le Fay is a witch who is part of Team Vali, Issei first met her in Volume 9. She is a huge fan of Issei's TV series Breast Dragon Emperor Oppai Dragon (short also Oppai Dragon), she wanted to shake his hands with him and get an autograph on her first meeting. She later gave him advice on how to increase his magical power and advised him which magician to choose for a pact. According to Ravel, she would have been the perfect candidate for Issei, but Le Fay had to refuse because as a member of Team Vali she is branded a terrorist and should therefore not be associated with Issei in public. In the end, however, she was able to make a pact with Issei, as Team Vali was pardoned in Volume 16 and Arthur asked Issei to take his little sister on as a pact magician to protect her. Issei accepted this request and asked Ravel, who also had no objection, as Vali's team had been pardoned and Le Fay became a legitimate magician to hire.

Arthur Pendragon

It looks like Arthur has great faith in Issei as he puts his beloved little sister Le Fay into his care, believing that she will be able to protect her and allow her a normal life, there she is his pact mage. Issei accepted Arthur's request and he intends to pay him back at some point.

Khao's Brigade

Shalba Beelzebub

Issei hated Shalba for his past action with Asia. Issei's hatred grew even more when Shalba went insane and saw Ophis as nothing more than a tool to increase his own strength. When Shalba saw the world that once rejected him, he decided to destroy the underworld and kill the children with the help of Bandersnatch and Jabberwocky. When Issei saw this he immediately registered that he had gone mad and went to kill him to protect the children and Ophis. Shalba was the first person to kill Issei himself. Ironically, Shalba also managed to kill Issei with Samael's poison, but it turned out that only the body was destroyed but not his soul.

Cao Cao

Cao Cao's relationship with Issei was initially rather hostile, as the former was a former leader of the Khaos Brigade and had kidnapped Yasaka. Cao Cao defeats him pretty easily in their first match against each other, awakening Issei's Illegal Move Triaina. In the ensuing fight, Issei succeeded in removing one eye from Cao Cao, which he replaced with the eye of Medusa. Issei's dislike grew even more when he came to attack his friends and to steal the strength of Ophis. Issei is highly regarded by Cao Cao after the last fight, especially after his return from the dead. Cao Cao believes Issei was a real monster when he appeared on Great Red's back and didn't believe it was just luck. The injury he inflicted on him the last time they met became a major factor in the final bout. Issei managed to use Samael's poison on Cao Cao's Medusa eye, which caused Cao Cao pain on an almost fatal level.

Euclid Lucifuge

Euclid is Grayfia's little brother and Rizevim's right-hand man. Issei's relationship with Euclid was hostile from the start, as Euclid was responsible for attempting to kidnap the First Year Occult Research Club members and attack them with several mages. He was also involved in the resurrection of the Evil Dragons.

In addition, Issei and Ddraig later developed a personal grudge against him, as he made a copy of the Boosted Gear from Issei's remains, in which he sacrificed several famous dragons for it, even Vali was appalled.

In Volume 16, when the two competed against each other, Euclid Isseis overpowered Cardinal Crimson Promotion in his own Scale Mail. This was possible because he has the power of a Satan even without a Balance Breaker. Issei was only able to win because a new strength awoke in him. There are theories in which Euclid Issei continues to observe in order to learn new techniques.



Ddraig is the dragon who is also called Red Dragon Emperor became known, he lives in the Sacred Gear / Longinus Boosted Gear of Issei. He gets along well with his current owner, but gets a bit depressed later when everyone starts him Oppai Dragon He needs medical treatment and psychological counseling because he is a proud dragon, but his reputation is destroyed by this nickname. He is very interested in Issei, because he never gives up to protect the people he loves, and he's been the first to talk to Ddraig so much for a long time and doesn't just see him as a tool. When Issei died he was devastated and told Ophis that he was the best owner he has ever had. He comes back later with Issei.


Tannin is the dragon Issei trained with in the underworld. He was responsible for getting stronger and reaching his balance breaker. Both have a close friendly relationship that goes so far that Issei calls him "Old-Man" Tannin. Both are very good friends and have fought many fights with each other. He used to be a Dragon king and knew Ddraig before he was sealed.


Issei officially met Ophis at his home when Azazel brought her to talk to her. At first he was afraid of her, because he thought she would kill everyone without blinking an eyelid, but it quickly turned out that she never had such intentions, but only wants Great Red to be expelled from her birthplace of the dimensional column. At first she was very interested in him because she wanted to know how Ddraig was, how he reacted with Issei and how his color changed from red to purple. In Volume 11, Issei became Ophi's first friend and he invited her to live with him at the Hyoudou residence. Ophis is also Issei's last friend (according to Ddraig) before he gets his new humanoid dragon body. She plays a huge role in resurrecting him with the help of Great Red in Volume 12 and now lives with Issei. Volume 20 shows that Issei is very worried about her and he was furious when she was attacked by Nidhöggr. It turns out that she is also very concerned about Issei, since he was her first boyfriend.

Ophi's behavior is similar to that of a child, she likes to do what she sees in others and would like to do the same things that the other girls do for Issei.

Great Red

Issei's relationship with Great Red is a bit vague as he doesn't communicate often and mostly sends messages through Ddraig. However, he is ready to save Issei and Ophis when their pocket dimensions threatened to collapse and brought them to him in the dimensional gap. He was also ready to make a new body for Issei from his own flesh.

Since Issei's current body was made from the flesh of Great Red, he has no problem connecting with its power. Issei sees him as one "Super-Strong Delinquent" because he just loves to fly through the dimensional gap and reacts aggressively if you just look at him. Issei is apparently embarrassed by Great Red's fondness for the Oppai Dragon themed song and this is the only time the two have communicated directly with each other so far.

Other characters

Issei's parents

Aside from the fact that Issei keeps complaining about his parents, he loves them very much. When Vali considered killing Issei's parents in Volume 4, Issei's parents got angry and immediately wanted to kill Vali. Issei's parents are like any normal parent who is proud of their child and loves him. His mother even stated that she was concerned about what a bad lustful influence Matsuda & Motohama had on Issei.

Matsuda and Motohama

These two are Issei's best human friends that he has, together with him they form the "Perverse Trio ". The three of them are mostly busy in the girls' locker room when they are out together or watch / read porn together, but when the going gets tough they are both willing to leave Issei behind so he can get into the trouble. The two of them are very jealous of Issei's newfound popularity with the ladies and therefore have fun spreading nasty rumors about him.


Issei's first interaction with him started a bit bumpy as he doubted his ability as a demon and wanted Koneko. However, both became friends through their favorite children's series Dragonball ("Drag So-Ball" in the anime).


Despite Issei's continued trepidation towards him, he finds him a nice person. The two have a good relationship with each other.

Aika Kiriyuu

Issei complains that Aika is constantly telling Asia about erotic things or teaching her. The two seem to get along well if the two are not at odds.

Aika knows Issei is a demon because she is Xenovia's regular.

Kiyome Abe

She first met Issei when Rias had to write a report about Yokai in Volume 8, but she didn't want to help because she was afraid of losing her soul if she got involved with demons. However, she agreed, on the condition that the Occult Research Club would have to beat her and her team in tennis and if Rias lost she would have to temporarily give up Issei. Unfortunately, she lost the match and had to write the report. Later, Kiyome asked Issei if he could help her break the engagement that her father had arranged for her. Issei decided to help her in the beast battle against her father. She fell in love with him during these events.


Kunou is a youkai from Kyoto and the daughter of Yasaka, the ruler there. She first suspected Issei that he had kidnapped her mother and attacked him and his friends because of that. After he freed her mother from the captivity of the Hero Faction, she fell in love with him and said she would wait for him forever.