Hachiman is a loner with no close friends and is a social outcast. The only person he is close with is his younger sister Komachi. Throughout the series he learns to be more social and develops good relationships with classmates and peers.
Hachiman has an annoyed but loving view of his parents. He thinks their relationship is good, but is bitter because he believes Komachi gets treated much better than he does as she is the "favourite" child.
Both of Hachiman's parents are unnamed and are corporate workers. They are always either late working or outside running errands. Hachiman considers them corporate slaves and wishes to avoid that lifestyle.
Hachiman is still upset at his parents, as they rarely visited him while he was at the hospital after the car accident he was in. It was mentioned they only visited on Thursdays.
Hachiman felt embarrassed to go on a family vacations after middle school. His parents accepted his decision easily and went without him. This annoyed Hachiman, because he hoped they would try and talk him into going.
It was mentioned that they never celebrated Hachiman's birthday, but they went out shopping during Komachi's birthday.
Mr. Hikigaya is over protective of Komachi and seemingly careless for Hachiman. He claimed that he will kill any boy who attempts to be close to her, even Hachiman.
They participated in father-son recreational activities such as playing table tennis when Hachiman was younger.
He bought a gaming console for Hachiman, but bought a wrong one due to an unfamiliarity with video games.
According to Hachiman, his father would give him useless advice whenever they talked. They also share a love of books as all the books in the house belong to them. They also share a desire to be overprotective of Komachi.
Hachiman says his mother is more lenient and kinder to him than his father.
His mother is very caring, she often cleans his room and asks him how his day went. He considers her to be like Komachi.
She even organized and stacked his porn magazines when cleaning without mentioning anything.
She cares for him by cleaning his room without him even asking, putting a blanket over him while he's sleeping, and warning him not to be involved in another accident. She even gives him money for going out.
Hachiman is sometimes irritated with his mother and believes she doesn't like him as much as Komachi. He is angry that she somehow misspelled his name on a birthday cake once, she also sometimes gives money just to Komachi when the two of them go out together.
Komachi says their grandparents are sweet and like to spoil their grand-kids. Hachiman explains that they tend to be sweeter with their younger grandchild (Komachi).
Growing up together resulted in them gaining a close sibling relationship despite being polar opposites in terms of personalities. Because their parents are mostly never home, Hachiman and Komachi spend much of their time taking care of each-other at home making them even closer.
Hachiman cares for his little sister a lot. Some people, even Komachi, jokingly viewing him as a siscon because of it. He is very protective of his sister as he disapproves of her friendship with boys, namely Taishi Kawasaki.
When Komachi was in elementary school, Hachiman did all the household chores which are now mostly done by Komachi.
Komachi is initially the only person Hachiman is willing to talk to about his personal problems with.
The two of them have a running gag where they express their love for each other on a "point system" where the more lovable the phrase, the more points they get.
His rotten personality is something Komachi learned to deal with, though she has her limits and can be truly bothered when Hachiman acts slightly more indifferent to her than usual. She can hold a grudge about it for days, she also forgives him easily with just an apology on his part.
While Hachiman doesn't want his sister near boys, Komachi often meddles in his life by trying to set him up with various girls in the series.
Sobu High School Edit
Shizuka is his teacher, adviser, and counselor. They have a very relaxed and personal relationship. She frequently scolds and physically disciplines Hachiman to make him get his act together. Hachiman often instigates her actions by making comments about her age, behaviour, or hobbies. Despite that, she genuinely cares about his well-being, enough to force him to join the Service Club, and to give him her phone number.
Shizuka often keeps track of him, either in person or through Komachi.She also hints that she knows about his accident, but to what extent and whether she knows of other members' involvement is questionable.Shizuka understands Hachiman's actions during the incident with Sagami, but instead of scolding him, she gently reproached Hachiman by stating that helping others is not another reason for him to hurt himself, because there are others whose hearts will break just watching his self-sacrifices. She says even though the results of his actions ended well, she won't commend him for it.
Hachiman feels that if he was born 10 years earlier and met Shizuka, he probably would have fallen madly in love with her.
After having been forced by his homeroom teacher to join the club, Hachiman has been made to interact with its other members. Hachiman was initially cautious of building a relationship with the other members but eventually loosened up. Over the year Hachiman has completed many student requests with the club and has gotten to know Yui and Yukino better.
Hachiman learned the other members were connected to his past car accident and withheld this information from him. He became mistrustful when he found out and slowly distanced himself from the other members. He soon forgave them as he realized they were each trying to talk to him about it in their own way.
Hachiman first met Yukino during his initial visit to the Service Club. Even before meeting her personally, he knew of her as the top student in his grade. Hachiman also considers her to be the prettiest girl in school.
Hachiman first believed her to be stuck up, haughty, cold, and brutally honest. Regardless, they are shown to possess similarities as they were both social outcasts who were ostracized by their peers. Hachiman tried to use this as a way to befriend her but was immediately turned down.
They develop a banter based relationship with them casting insults at each other.Yukino is fond of calling him a variety of nicknames by intentionally mispronouncing his name in an insulting way (Hikigerma, and Hikikomori-kun). She also pretends to forget his name sometimes. In return, Hachiman calls Yukino the Ice-cold Beauty and Demon Superwoman for her personality and skill. Or Yukipedia due to her wide range of knowledge.
Yui once referred to the banter between Yukino and Hachiman as "in-jokes", which she finds difficult to join in.
After spending more time with each other, Yukino reveals more of her feminine side around Hachiman whenever they are alone. They have gone shopping or met each other for different reasons several times. Offering him snacks and drinks, and sometimes giving him gifts.
Hachiman held a perfect image of Yukino in his head. Someone who could not lie, was smart, and flawless in almost every way. Eventually he finds out that she was in the vehicle that hit him but pretended not to know about it. From this realization, Hachiman's image of Yukino was shattered and admits that it was wrong of him to force his ideals on others. They eventually reconcile and Yukino hints they might have become friends.
Despite "rejecting" him as a friend, she still trusts him to a high degree and finds his "social suicide" plans 'irritating'.
During Tobe's request, she defends Hachiman's actions and asks Tobe to stop being rude to him.
After the completion of Tobe's request, Yukino expressed her hatred for Hachiman's methods. She was angered by Hachiman's plan for Iroha's request. She became hostile towards Hachiman until he went to the Service Club to request help in finding something "genuine".
She admires Hachiman because he can be himself.
Late in the series Yukino is shown to trust Hachiman a lot more, even revealing part of her past involving Haruno and Hayama. She even asks Hachiman to "save her someday".
It is hinted that Yukino may have developed romantic feelings for Hachiman but won't act on them because of her family situation and current friendship with Yui. Yukino doesn't want to jeopardize her relationships with the very first people to accept her for who she is.
Hachiman has demonstrated feelings of care and trust for Yukino, but has not committed to her (or anyone else) romantically because of his personality and due to his bad luck with girls in the past.
When Hachiman first met Yui he believed her to be a typical popular girl. Someone who is only interested in fashion, boys, and parties. Yui is friendly even towards strangers like Hachiman, nicknaming him "Hikki" in an affectionate manner at their first meeting. He does not like the nickname because it sounds like Hikikomori.
Yui reveals herself to be a kind but air-headed girl. Hachiman mistrusts nice girls because he believes they either have an ulterior motive or don't mean what they say. His belief is reinforced when he learns from Komachi that Yui was the owner of the dog he saved on his first day of high school and how she brought sweets as thanks. He never knew because when Yui visited his house he hid. Hachiman believed Yui was only being nice to him out of guilt.
Hachiman ends up breaking off their friendship due to his belief. However, he is surprised when Yui is genuinely upset and leaves in tears.
Though he intended to maintain his distance from Yui, Yukino pressures Hachiman into helping her apologize to Yui and mend their friendship. The strain in the relationship is repaired after Yukino helps clear their misunderstandings during Yui's impromptu birthday party.
Yui is one of the few to have Hachiman's personal number and Mail ID (while the rest are Shizuka, Zaimokuza, Saika, Taishi, Komachi, and Hayato).
Always acting open and cheerful towards him, they get along quite nicely, though Yui sometimes finds Hachiman's rotten personality and distorted views annoying or misguided. Hachiman is frequently frustrated with her upbeat attitude and doesn't hesitate to call her an idiot when she is particularly air-headed.
Yui offered to organize and celebrate Hachiman's birthday party but Hachiman turned her down.
On Komachi's insistence, Hachiman ended up accompanying Yui to the end of summer fireworks festival. During the fireworks display, both Hachiman and Yui realize Yukino's car was the one that struck and injured Hachiman. After this Hachiman walks Yui home. On the way back, Yui cleared up the earlier misunderstanding, claiming that the accident wasn't the root cause for her behavior towards him. At the end, Yui appeared to be about to confess her feelings to Hachiman, but an incoming call from her mother interrupts her. Although she seems determined to ignore the call and continue on, Hachiman (who seemed aware of her purpose) urges Yui to take the call. After the call, Yui thanks Hachiman and hurries home.
During the Culture Festival, Yui offered Honey Toast to Hachiman. When Hachiman wanted to pay, she asked him to take her out to Pasela (Karaoke Chain) instead. Hachiman requested time to think about it, to which Yui agrees happily.
Yui paired up with Hachiman during their field trip to Kyoto.
They appear to have grown close as they developed the habit of walking together to the Service Club after class.
It is heavily hinted that Yui has romantic feelings for Hachiman.
Yui grew tired of waiting for the date Hachiman owes her. She invited him to the Tokyo Sea Life park, but also invited Yukino. Yui requests that their friendship remain the same regardless of how they all might feel. Hachiman rejects her idea in favor of searching for something genuine.
Saika is also one of the few people who truly tries to become friends with Hachiman, despite the latter's attempts to stay a loner. He is also one of the few people who admires Hachiman for his hidden kind and straightforward personality.
Hachiman initially thinks Saika, due to his appearance and mannerisms, to be female until Yui told him the truth. Hachiman has to remind himself on occasion that Totsuka is male. Sometimes he even questions if that would matter in their "relationship" before snapping out of his thoughts. It is hinted that Hachiman may see Saika as a friend which is a contrast to others. Their close association often worries Hachiman's sister Komachi Hikigaya.
Hachiman once paired up with Saika for tennis. Saika also asked Hachiman personally to join the Tennis Club to help raise their strength. Hachiman is hinted to have a romantic attraction towards Saika but reminds himself of the latter's gender, as shown as how he's contantly calling Saika and his actions "cute" and, as shown in the anime, always see's sparkles that indicate Saika's cuteness whenever Saika comes running to Hachiman. He has been in the same class as Hachiman for two years but was unaware of it.
Saika often shows interest in teaming up with Hachiman in many occasions like the workplace trip, summer camp etc. Saika was able to tell when Hachiman was depressed or feeling down and attempt to cheer him by taking him to the arcade. Saika was the first person to officially hang out with him, In the Light novel, they went to movies during summer vacations.
They had often paired together in the past for gym and similar activities, due to them both being outcasts of their class. They appear to be good associates, although both deny they are actually friends due to Yoshiteru's eccentric personality and weird habits. Though Yoshiteru seems to view Hachiman as an acquaintance because of their time in class.
Yoshiteru trusts Hachiman enough to share with him his ambitions of becoming a writer, and Hachiman cares enough or can tolerate him enough to help him out by giving him harsh and critical, yet meaningful, feedback.
They seem to have comfortable conversations and are on good terms with each other. Furthermore, after the rooftop incident, Zaimokuza is among those who know the real truth behind Hachiman's provocation of Sagami, and admires his courage as he gives a nod of approval and a smile. These show Yoshiteru greatly respects Hachiman for his ability to speak his mind and take down those who deserve it.
Hachiman and Zaimokuza understand each other well, due to them having similar interests and both of them being loners.
At first, Hayato acknowledged and credited Hachiman for the brilliant solution for the false chain message incident, and even thanked him for it. But during the Chiba Village summer camp and Sagami incidents. Hayato starts to hate how Hachiman can only do things in such negative ways. Even though he can understand the reasons behind Hachiman's methods, he refuses to acknowledge his "successes".
Even though Hayato hates Hachiman's methods he still tries to defend him from others negative opinions. He also stops people from bullying Hachiman in front of him. Shown during the double date with Kaori, and putting a stop to Tobe's name calling. Hachiman attributes this to Hayato's "Nice Guy" persona, and feels like he isn't genuine.
In Episode 11 of season 2, Yumiko requests that the service club find out Hayato's career path. Instead Hachiman gives advice to Hayato, telling him he can do what he wants, and advises him that the science courses have fewer people and he could be himself. Hayama rejects his ideas and reveals that he hates Hachiman and says it's not possible for them to get along. Because he often feels like he's lost to Hachiman, something that Hayama can't cope with due to his inferiority complex. In order to deal with his feelings of losing to Hachiman, Hayama attempts to elevate Hachiman to be equal so that he could accept losing to him.
Hayato once revealed that he was unable to solve Yukino's bullying problem by her jealous classmates at their previous schools and believed that if Hachiman attended the same schools as them, things would have turned out differently. Hayama also hints to know things surrounding Hachiman while he doesn't, as he says that "Now I know why she looks out for You" .
Later in the series Hayato refuses to help Hachiman for some of his requests. Hayato admits he has an inferiority complex to Hachiman and that he hates him. After the school marathon Hachiman tells Hayato that he hates him too.As it stands they are opposites of each other. They have both admitted hatred and respect for one another. Thus an unusual and strained relationship exists between them. However, he find it in him to praise Hachiman for his idea of pre-valentine event, that involves not hurting anyone..
Hachiman meets Saki on the roof in the Light Novel, and in the classroom during the anime. Saki is her typical cold and aloof self, even casually insulting him when he sees her panties. After Hachiman resolves her problem (Taishi's request) she seems to show respect to Hachiman, even seemingly befriending him. The interaction between Saki and Hachiman is focused on more in the Light Novel than in the anime. It is later hinted in the light novel that she may have feelings for Hachiman by her reactions to him. While Hachiman studies people and is usually right in his deductions, he does not seem to notice Saki's feelings or seem to put thought into them.In the haunted house during the field trip, she was seen clinging to Hachiman's blazer for protection. Saki also contributed her help to save the service club. It is also seen that Saki knows Hachiman's leadership abilities when she considers him a valid Student Council President candidate. In episode 12 season 2, when Kaori wonders whether she has given Hachiman Valentine chocolates before, Saki seems curious. In the light novel, Saki also pointed out to Hachiman that she packed some of her own hand made chocolate along with Keika's valentines chocolate for him.
Like most of the popular kids, Ebina calls Hachiman "Hikitani-kun". It's eventually revealed that she does that on purpose, but jokingly, because in episode 10 she writes Hikigaya's last name correctly on the board for her yaoi play. She also wrote Hachiman's first name correctly in the survey by service club for Love and Marriage column of a magazine. This makes her one of the two popular kids (Hayato another) to know his true name.
She seems to like the idea of Hayato and Hachiman being a couple, due to her love for BL and she always makes a strange giggle whenever they are seen together.
Hachiman doesn't pay her much mind but seems to get along with her better than the other popular students, though he is put off by her interests.
When she learns that Tobe is about to confess to her, she indirectly requested Hachiman to stop Tobe from confessing to her in order to maintain her cliques status quo. She thanked Hachiman personally when it was done. She also hints that she might like to date Hachiman, but he rejects her idea. Ebina eventually tells him that she hates herself for always being selfish with her desires and that she is rotten.
Tobe is the first person to mistakenly address him as Hikitani, which becomes an informal nickname, which results in his clique members to call Hachiman the same. After the Chiba Village summer camp incident, he started to have a very negative opinion on Hachiman, and felt that he is seriously terrible person.
At the end of the cultural festival, he shared his opinion to everyone within earshot. He even made fun of Hachiman by referring him as Somethingtani-kun . In the Service Club, he refused to state his request in the presence of Hachiman as he felt the latter had "zero reliability". As the series progresses, Tobe started to understand Hachiman better, which can be seen during the school field trip.After the field trip Tobe casually talks to Hachiman in a friendlier manner than before, hinting that all his negative opinions on the latter has vanished. But he still believes Hachiman's name is Hikitani and even continues to address him as such, much to the former's irritation. Hachiman also begin to see good points in Tobe and describe him as a nice person in his private conversation to Hina but still felt him to be annoying .
Hachiman greatly admires Meguri as his senior, he views her as a cute and reliable student council president to lead the school. She is one of the few people to acknowledge his skills, even though she can't recollect his name often at first. She is one of the few to know his leadership skills, given that she asked Hachiman to become a committee member for sports festival despite the rooftop incident. While she initially had a bad impression of his actions, this moment shows she later came to an understanding on the intent behind the event, and does not see Hachiman in a bad light because of it.
After Iroha was elected, she spoke with him and expressed her hope that Yukino, Yui, and Hachiman were going to take over student council instead. She would have liked to sometimes hang out with them even after graduation. This showed she sees him as worthy of a higher status in school.
Iroha and Hachiman first encounter one another during the Judo tournament (In the Light Novel), but it isn't until her request regarding the student council election that they truly become acquainted with one another (First meeting in the anime). Hachiman's first impression of Iroha was that she was an uncute version of Komachi, in others words a person with a sly personality, but lacking in substance from his point of view at the time.
Eventually, Hachiman starts to see through Iroha's lively and air-headed persona, and recognizes her as a sly and intelligent person. He also notices that her lack of confidence and vulnerability, which is the main reason she pretends to be happy all the time.
After Iroha became the Student Council president, Hachiman begins to feel guilty for pushing the role onto her and volunteers to help her out. Hachiman starts to treat Iroha like a little sibling, and Iroha in turn starts to rely on Hachiman and asks for his advice and help. Hachiman always gives in to her unreasonable requests because he feels like he has a responsibility to look after her, much like Komachi.
There was a turning point in their relationship, as after she was rejected by Hayama. While being comforted by Hachiman, Iroha shifts the conversation to him, and reveals that she overheard Hachiman's desire for something "genuine", during his request towards the Service Club. Hachiman is embarrassed, but instead of mocking or laughing at him, Iroha admires his honesty and says she'll never forget it. She declares that she also wants something genuine. Hachiman states that she is a pretty amazing person, she claims that it is his fault that she became this way.
A running gag of the series, is Iroha's misunderstanding of Hachiman's words as a confession towards her and a quick rejection. This irritates him but very soon, he gets used to it and ignores her as he sends her on her way, which gets an irritation from her as well.
In light novel Volume 10.5 (OVA 2), the two even go on a "date", where Hachiman admits (internally) that he finds Iroha to be cute even with her sly personality. During the date, Hachiman suggests going to two separate movies and meeting up later, instead of agreeing to be separated, Iroha decides they should play ping pong together instead. After a match of table tennis, Hachiman complains to Iroha about her being "unfair" by trying to be too sly and foxy to get him off guard. She replies that being unfair makes her more of a woman, as she whispers into his ear that he is the only one she will act this way towards.
For the Pre-Valentines event, she was surprised and seemed jealous when Kaori Orimoto asked Hachiman if she ever gave him handmade chocolate. After this, Iroha gave him some handmade chocolate as Hachiman was surprised that she seemed skilled in a kitchen. In the Light Novel, Iroha gave a bag of Valentine's Chocolate to Hachiman and asked him to keep it a secret from everyone else.
Minami Sagami Edit
Sagami looked down on Hachiman when she first set her eyes on him at the fireworks festival. At first sight, Minami viewed Hachiman as a social outcast and a loser. Hachiman however, is fully aware of Minami's true personality but chooses to just not care about her, instead of hating her.
After their encounter at the fireworks festival, Hachiman tried to just ignore her, but was dragged into matters when they were chosen to be the male and female representatives for the Culture Festival planning committee. Hachiman is the first member of the entire committee to point out to everyone how much most of them (especially Minami) were irresponsibly using Hachiman and Yukino to slack off.
Hachiman often criticizes the way Minami is handling her responsibilities as chairperson of the Cultural Festival. He comes up with a mocking slogan, and openly complains to Hayato when he stops by.
Things became even worse when Minami ran away and hid during the Cultural Festival. When Hachiman managed to find her, she resented him for it as she was longing for someone more popular to do so as Hayato and her friends show up. Realizing her intentions, Hachiman finally had enough of her behavior and tells her off for her treatment to him. In his speech, he reveals true feelings by stating he knows she accepted her position simply because of the popularity she gets and wanted to be someone who can look down on others. While doing so, he vilifies himself as her friends and Hayato (who is aware of the real purpose) console the now speechless Sagami who realized how outspoken Hachiman was than she thought.
In the light novel, Minami would neither join nor stop her clique members from badmouthing Hachiman, but she wears a downcast expression every time his name is mentioned, as she is still unable to forget his harsh words during the rooftop incident.
Because of his actions to Sagami, Hachiman's reputation saw even greater decline as most people recognized him as the person who hurt Sagami's feelings. However, through this he was no longer ignored or unregnosized. He also paid the incident no mind as he was being honest to a person who needed some harsh reality.
In Volume 6.5, Yui notices Minami's disdain towards Hachiman, which Hachiman does not seem to mind and instead he appeared to feel proud of.
They started to get along better as Minami puts in more effort to help the Athletic Festival. Minami took Hachiman's advice to "bring the hammer down" on her opposition from the Athletic Festival.
After the Athletic Festival, Yui and Yukino feel that Sagami has changed, since she didn't give away the person (Hachiman) who broke the rules during the Botaish event and stated the foul in a round about manner. When Hachiman and Minami crossed paths in the hallway, she only tells him to get out of her way. Hachiman notices their relationship is neutral and is okay with the result.
Due to being an outcast, Hachiman was either ignored or overlooked by his classmates. Most of his classmates view him as gross, creepy and even a pervert, especially from girls. In return, Hachiman is not all bothered by his seclusion from others even being proud of it and is annoyed when meddlesome sources such as his teacher, sister or others try to get him to affiliate with others.
While he was initially seen as a nobody, he has gained some acknowledgement for being the student who hurt the feelings of Minami Sagami after the rumors emerged. Some know the real reason and praised him for it, while others gave him angry or mocking glares for his assumed cruelty but nobody picked on him nor did they mistreat him.
Fortunately, this bad standing blows over as time passes, especially after the trip to Kyoto. However, he is still not seen as popular by others but is not mistreated as he told his sister that nobody is picking on him.
Haruno likes to tease Hachiman about his "relationship" with Yukino and Yui. She constantly addresses Hachiman as her future brother-in-law, much to his annoyance.
Haruno knows Hachiman was the person hit in the accident that Yukino was involved in. She makes a joke about the car at the firework festival, and realizes that Yukino hasn't told them about the accident. She then quickly stands up for Yukino saying she was not driving the car and was at the back seat (which would be unnecessary if she didn't know Hachiman was involved). It is unclear if she knows that Yui is the other girl involved.
Haruno sees Hachiman as an intriguing person, most notably due to his ability to analyze peoples behaviours, but incapability of understanding the emotions behind their actions. It's a trait that made her declare him a "monster of logic". While Haruno usually takes a very provocative and aggressive demeanor in the presence of Yukino, she is noticeably more casual when alone with Hachiman.
For personal amusement, Haruno also sets-up Hachiman and Hayato on a double date with Kaori Orimoto (the girl who rejected him) and her friend, she even spied on them throughout the date.
Hachiman despises her and is frightened by Haruno's aggressive and sly personality, but states after he was able to see through her facade, she hadn't bothered trying to hide her inner face.Volume 9). Rumi is more open to Hachiman during their conversations, since both of them are fellow loners and ostracized by their peers. She avoids Hachiman after the "test of courage", while she had no issue approaching him before. She might know about his involvement in the unusual "test of courage".
During the Christmas collaboration event between Sobu High and Kaihin Sogu High, they meet again with Hachiman and Rumi making Christmas tree decorations together. Hachiman sees that his method did save her from bullying, but he feels that it was not enough as her solitary aura still remains. Her status is what gave Hachiman the final push to realize his methods were not effective, solving the short term issue but not truly doing anything to fix it.
As it stands Hachiman is fond of Rumi, as Rumi seems to look up to Hachiman who can better understand her situation.
Hachiman meets Taishi through Komachi, who brings Taishi to him with a request involving his sister, Saki. Hachiman is initially cold towards Taishi due to his closeness to Komachi. Even though Hachiman dislikes Taishi, he did the most in finding a suitable solution to Taishi's request. Hachiman is able to understand Taishi better than Saki.
In the light novel it is shown that Hachiman slowly warms up to Taishi, offering advice about his High school choice and girls.
Taishi is respectful towards Hachiman, as he frequently calls him big brother and holds him in high regard. He believes Hachiman is smart and popular with girls.
Keika is very fond of Hachiman and calls him "Haa-chan". Mostly they play whenever they meet, this shows Hachiman has no problem with her.
In light novel, Keika had offered Hachiman a bag of Valentine chocolates and kept clinging onto him.
Kaori was Hachiman's classmate and previous crush in middle school, she was cheerful and enthusiastic causing Hachiman to think she liked him. Hachiman had asked Kaori out, but was immediately rejected and they never spoke again. Her rejection of Hachiman has great impact on him, as it led to bad rumors of him and causing him to hate all "nice girls" (such as Yui) and set him down on the path of a loner. Due to that, he became more capable of talking to other girls without any problems or nervousness but has a developed jaded view on women just as they have on him.
After middle school, Hachiman opted to distance himself from his past and middle school classmates by going to another school.
By complete coincidence Hachiman, while out with Haruno Yukinoshita, meets Kaori again in high school. She is only interested in getting to know Hayato through Hachiman since she knew he went to school with Hachiman. While Hachiman wanted nothing to do with her, an intrigued Haruno meddled and got Hayato to come and meet Kaori and her friend.
Kaori sets up a double date with her, Chika, Hayato, and Hachiman, but she fails to let Hachiman know. During the date, Kaori's cheery yet ignorant behavior towards Hachiman is seen until Hayato points it out to her by showing his associations with Yui and Yukino. In return, Hachiman, no longer a young kid, realizes she was like this all the time and its made obvious that Hachiman no longer holds any romantic feelings for Kaori as he even belittles himself for thinking he liked her.
Due to the events of the double date, Kaori's attitude towards Hachiman seems to have changed and is more considerate of what she says about him because of Hayama's criticism.
In one meeting, he and Iroha Isshiki are walking together when they meet Kaori who Hachiman was surprised to see. Unlike before, Kaori was nervous when meeting him and Iroha Isshiki and not saying much about their relationship but denied that they were close. Hachiman was very confused by her sudden change in demeanor and wondered what had brought this change about.
It is likely through Hayato's words she has come to see that there is more to Hachiman than she thought there was. Though she still maintains her casual nature around him, which was shown in one meeting in which asks him if he is dating Yui Yuigahama, Yukino Yukinoshita or Iroha Isshiki while stating she must have underestimated his popularity in the past.
During one meeting, Kaori buys him a drink and mentions there was more to him than she realized. She stated she didn't see that as she didn't try to make the effort in knowing him very well back then. Kaori brought up his past confession and says that Hachiman still isn't boyfriend material in her opinion, though he voices he is no longer interested in her. However, he is surprised after she states that she wishes they could be friends and thus wants to patch up the relationship between them. After that, she invites him to their middle school reunion, which he immediately turns down while she laughs thinking its a joke.
It is unknown if Hachiman ever truly considered her offer of friendship or still chooses to keep his distance from Kaori, due to probably thinking it was out of pity and his dislike of it.
They met again at the pre-valentine collaboration event, where Kaori asked Hachiman for his help with something. After he helps her, she questioned if she ever gave him valentine chocolate, to his surprise and the other girls' jealousy. Kaori went through with it and Hachiman received chocolates from her, Yui, and Iroha.