Due to his status of being a social outcast, very few people interact with him and some try to avoid speaking to him. Though the characters who do interact with him personally show their true natures to him, due to him somewhat seeing through them or because of his poor reputation. However, this is done when they are privately talking to him.
Both of Hachiman's parents are unnamed and are working in a corporate company, so they are always either late or outside, thus rarely mentioned in the series. Hachiman considers them corporate slaves. It was mentioned that they never celebrated Hachiman's birthday, but they went out shopping during Komachi's birthday. They are mentioned to sleep till afternoon during their weekends and days off. In the light novel and manga, Hachiman woke up his mother by accident and she is grumpy but not necessarily mean. Both of his parents seem to prefer Komachi over him, though its clear that in spite of their favoritism they do love him as well.
Hachiman was still bitter with his parents, as they rarely visited him while he was at the hospital after the car accident. It was mentioned they only did so on Thursday and not daily. Hachiman felt embarrassed to go on a family vacation after middle school, while his mother respected his decisions, his father was overjoyed to spent more time with his wife and komachi without Hachiman. This kind of annoyed Hachiman, as he hoped that they will try to pursue him to come along instead of readily agreeing.
In the light novel, it was mentioned that their father is very protective of Komachi to the point that he claimed that he will kill any boy who attempts to be close to her, even Hachiman. Furthermore, his father didn't seem as fond of him as he is of Komachi. However, they participated in father-son recreational activities such as playing table tennis when Hachiman was younger. His father at one point bought a gaming console for him, but bought a wrong one due to unfamiliarity with such device. According to Hachiman, his father would give him useless advice whenever they get a chance to talk, like how the sales girls are only after his wallet and all other useless stuff. During a weekend, Hachiman purposefully slammed the door while leaving the house to disturb his father's sleep.
His mother is more lenient and more kinder to him than his father. In volume 11, when answering Yui and Yukino about his mother, he said she was like another komachi in the family. His mother was introduced in the light novel Volume 3 Chapter 3 and was also mentioned in Season 2 Episode 7. His mother is mentioned to wear specs. Her kindness for him is shown in the series from time to time like cleaning his room without him even asking, putting a blanket over him while he's sleeping, warning him not to be involved in another accident etc. She even gave him money for outing. She is also accepting of his teenage behavior, as she arranged the stack of Hachiman's porn magazines she found while cleaning his room without saying anything. However, during dinner she gave him a glare to warn him to be silent.
The power/privileged/social ladder in Hikigaya household is as follows:
Cat → Komachi → Mother → Father → Hachiman
In the OVA, Komachi mentioned their grandparents, she says they are sweet, but Hachiman explains that they tend to be sweeter with the younger one. This shows that like his parents, they favor Komachi over him but it is unknown if they have care for him as well.
As explained by 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 is the only companion Komachi has at their home thus making them even closer as they grew up.
Hachiman has been shown to care for his sister to a great deal with some people, even Komachi herself, jokingly viewing him as a siscon because of it, though he angrily denies it as it is clear that this is not the case since he has shown no other interest in her besides her being his family. Some of the mocking is attributed to the girls (Yui and Yukino) being jealous that he opens up more to his sister than with them, due to their feelings for him. He is very over protective of his sister as he disapproves of her friendship with Taishi Kawasaki. It also makes him angry to the point of adding Taishi to his "Unforgivable People List".
When Komachi was in elementary school, Hachiman did all the household chores which are now done by Komachi. In the series, Hachiman expresses how his relationship with Komachi when they were younger now seemed completely non-existent.
Komachi is the only real person Hachiman is willing to openly talk to about his personal problems and is genuinely happy with. The two of them also have a running gag where they express their love for each other and call it 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 from his part and she herself does so.
It is shown Komachi wants her brother to be happy and mostly meddles in his life by usually trying to pair up Hachiman with Yukino and Yui at every chance she gets, though is often frustrated with his non-interested nature. In return, Hachiman has shown that he is fully aware of his sister's true motives and is really annoyed by her frequent meddlesome attempts to set him up with girls, due to his past attempts which all ended in tragic failure. It is unknown if he ever told Komachi about these incidents in the past.
However, it appears that the only reason that he hasn't stopped Komachi or told her that he's really aware of her actions is because deep down he secretly appreciates her efforts as she's merely looking out for him, which is something he always wanted from others. This further proves that he enjoys having her as a sister, if she was willing to help him out even when she doesn't have to.
Soubu High School
As his teacher, adviser, and counselor, Shizuka frequently scolds and physically disciplines Hachiman to make him get his act together. In return, Hachiman does not her much respect and often instigates her actions by making comments about her age, much to her annoyance. 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.
Hachiman has shown to be really annoyed by his teacher consistent meddling in his life and forcing him to do things. As mentioned before, he often intentionally riles her up and always receives a hit for his words. However, it appears he somewhat appreciates her since she has caused him to change some of his outlook or activities. It also appears that the only reason he hasn't told her to stop is because she can understand some of his pain and he is actually grateful for her efforts.
She is also aware of what really happened during Hachiman's incident with Sagami, but instead of scolding him severely, 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 that the result of his works are good, but she won't commend him for it.
In Season 2 Episode 8, Hachiman feels that if he was born 10 years earlier and met Shizuka, he probably would have fallen madly in love with her.
Having been forced by his teacher to join the club, Hachiman has been made to interact with its other members. Hachiman has done many favors with the girls of his club and has got on good terms with them as they worked together.
Through other sources, he has learned that they were connected to his past car accident and withheld this from him. Due to his views as well becoming hurt at these revelations as he was growing to trust them, he slowly distanced himself from them, despite the girls' attempts to explain themselves for withholding the truth. However, he soon forgave them as he realized they weren't really at fault and he'd still be a loner even if the accident hadn't occurred. After some time with them, Hachiman has learned how to better approach other people and be on friendly terms with those people.
Its unknown if he sees his club mates as actual friends or acquaintances, though it has been seen that he doesn't mind them even though he does argue with both at some point due to opposing views. Also, he has unintentionally become the object of affection for his club mates who have displayed hints of attraction towards him because of their time together or getting to know him on a personal level. While its unknown whether he has any interest in them, he is hinted to be fully aware of the girls' feelings, after studying their behavior but chooses not approach their feelings because of his past failures with girls or his lack of interest in romance.
Due to meddlesome sources, he has been forced on various date like situations with both of them and while dismayed at first since he had no choice, Hachiman was shown having fun though tries to hide it out of pride.
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 which was notable as he didn't recognize Yui Yuigahama his own classmate. Hachiman considers her the prettiest girl in school (Volume 1 Chapter 1).
When interacting with Yukino, he believed she was a strict and honest person with incredible confidence, smarts, and talent. The two don't get along mostly because her personality causes her to belittle him and he is simply annoyed by her condescending attitude. 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 as a result, much to his annoyance. They somewhat got along, even if Yukino belittles him in whatever chance she gets while Hachiman can only make retorts at her.
When Hachiman and Yukino along with Komachi went out shopping for Yui's birthday, in which Komachi slid away creating a date-like situation, much to Hachiman's annoyance. Sensing the suspicion of the shop assistant and the surrounding customers, Yukino asked Hachiman to pretend to be her boyfriend to his confusion but he agreed as she was surprised at his answer. She was also flattered that Hachiman had called her cute in an apron she had picked out and bought it. She latter clung to him when she was scared of a dog (later revealed to be Yui's dog), these events showed she trusted him to an extent. In return, Hachiman was somewhat amused by her fear and saw that even she gets scared of things.
At Yui's party, after he and Yui reconcile, Hachiman noticed a remark with Yukino's statement about the incident that injured him when he saved Yui's dog. This caused him to wonder if she had any knowledge about the incident.
During a meeting with her sister Haruno Yukinoshita, it is revealed that Yukino was in the same car that struck Hachiman which left him hospitalized on his first day of school and indirectly set him on the path of being a social outcast. This in turn, reveals Yukino had actually recognized Hachiman from the car accident but pretended not to not know him in their formal introduction after he was forced to join the club and made no attempt to bring up the topic.
When Hachiman realized this, he was very surprised and greatly hurt that like Yui she withheld this knowledge from him. In a talk with Yui about the incident, he felt that the news shocked him and he would of like to have known about her knowledge of the event. As a result, he slowly distanced himself from Yukino despite her trying to explain herself after realizing he became aware of this event. It should be noted that he that he was more angry at himself, rather than towards Yukino when he found out about her deception and berated himself for not noticing sooner.
From this event, Hachiman's ideals of Yukino were shattered and admits that it was wrong of him to force his ideals on others, because of course she can lie and that Yukino isn't always what she seems.
During his distancing from her, Hachiman barely associated with her and Yukino appeared to be somewhat sad, possibly meaning that she was getting used to their talks. Regardless, the two slowly patch up their relationship as when they were put to work on the play, they are shown to rebuild some trust. When Yui drags him to Yukino's home, she is shocked that he was present and even look to him for some guidance but he barely put in any effort. Once during the Culture Festival, Yukino and Hachiman were bantering through the PA system of intercom until a planning committee person informs Yukino that their conversation can be heard by all in the intercom.
After the festival, the two finally talk about the accident once Yukino states she wasn't lying about not knowing him in their meeting but says she knows him now. He offers to be her friend a second time but was rejected immediately, only in this instance Yukino states it is impossible for them to become friends, this time with a warm smile and in a friendly manner. It is then that Yukino tells him that she really didn't know anything about him, but she knows him now, since they have spent a lot time together in the Service Club. Thus, she indirectly tells him that they could theoretically be friends.
Yukino is also fond of calling him a variety of nicknames by intentionally misspelling his name such as Hikicasting-kun, Hikifrogaya, Hikifroggy, Hiki-gay-kun (his childhood nickname), 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 from the start. He also calls her Yukipedia for her wide range of knowledge.
Yui once referred to the jabs between Yukino and Hachiman as "in-jokes", which she finds difficult to join in with them. This shows they have a closer relationship with each other than with Yui at the time.
Despite twice "rejecting" him as a friend, she still trusts him to a high degree though finds his social suicide plans 'irritating'. She is shown to care about him throughout the series. Offering him snacks and drinks, and sometimes giving him gifts.
After they have spent more time with each other, she tends to shows more of her feminine side around Hachiman whenever they are alone. They have gone shopping or met each other for different reasons several times. She admires Hachiman because he can be himself, and she expresses a desire to obtain something that Hachiman does not have, but she doesn't know what yet.
During Tobe's request, she showed her cold side to Tobe for bad-mouthing Hachiman, even stopping Hachiman from leaving as she explains she was talking to Tobe whose request she almost rejects unless he could be polite. This event surprised Hachiman, since Yukino was actually defending him from others instead of going along with the insults.
After the completion of Tobe's request, Yukino expressed her hatred for Hachiman's methods, she can't describe her feelings towards him and his actions and storms off. She was angered by Hachiman's plan for Iroha's request, rejecting it with a much more hostile emotion by giving every possible reason she could think of to oppose it at that moment. She is hostile towards Hachiman until he comes to the Service Club as a student to request help in finding something "genuine".
After Hachiman's emotional and tearful request to the club was completed, Hachiman thanked his club members to which Yukino states that the request is not over and that she will fulfill his request for something "genuine", a statement that somewhat shocks Yui and puzzles Hachiman. She tells Hachiman that she is beginning her search for it and will not follow her sister's shadow, and admits that she requires his help to achieve it.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", while on a ride at Destinyland.
It is hinted that Yukino may have developed romantic feelings for Hachiman but can't act on them because of her history and current friendship with Yui who also has feelings for Hachiman. 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. It is hinted that like with Yui, he may be aware of Yukino's feelings for him as well since he studies the behavior of others but he may not want to approach on the matter, due to his bad luck with girls in the past.
Hachiman initially believed Yui to be a typical "in" person, and one of the popular group. Yui is generally friendly towards people even Hachiman, calling him "Hikki" in an affectionate manner in their first meeting, much to the his annoyance and confusion (due to not knowing her despite being classmates). At one point, he rudely insulted her which she takes offense to but soon shrugs it off and joined the club after being impressed by his and Yukino's straightforward attitude.
At one point, she questioned him on his accident seemingly aware of it while he was confused by her curiosity. Hachiman soon learns from his sister that Yui was the owner of the dog he saved on his first day of high school and how she brought sweets as a thanks. He never knew because Komachi ate the sweets herself and forgot to tell him about Yui and her coming to see him.
As a result of this knowledge, due to Hachiman's jaded views, he comes to the belief that Yui's feelings for him are because of guilt and pity. Hachiman met Yui and called her a nice girl for her waiting for him on a field trip as she blushed at his words. However, he surprised Yui with his new knowledge about the accident, stating he believed her kindness to him stemmed from guilt because to the fact that he was the one who saved her dog, which consequently left Hachiman injured and hospitalized. He tells her to stop as even he would still be a loner even if it weren't for the accident. However, she denies that her feelings come from guilt but is brought to tears that he would think such a thing. Due to his harsh words, he indirectly rejects her and keeps her emotionally away. He believes that she was better off not knowing him at all for her own good.
Hachiman broke off his association with Yui, making her upset but he is steadfast on holding this act as he hates nice girls. This is relevant to note that Hachiman's actions during this arc were based upon his experience with Kaori Orimoto, a girl he confessed to in middle school due to his mistaken impression that her kindness towards him was out of romantic interest.
Though he intended to maintain his distance from her, Yukino pressures Hachiman into helping her in apologizing to the latter. Due to this, Yukino and Hachiman go shopping for a birthday present to thank Yui for her friendship. Yui's dog got loose and made it to Hachiman having recognized him for saving it. After catching up to the dog, Yui spots them unaware of their purpose and thinking they are now dating.
The strain in the relationship is repaired after Yukino helps clear their misunderstandings during Yui's impromptu birthday party. Hachiman didn't know what to give Yui for her birthday but though a gift for someone "less intelligent" (than Yukino) would be best. He presented her a dog collar for her pet Sable, which Yui mistakes for necklace/choker at first. She is upset with him outwardly, but is shown to be pleased with the gift and runs off happily. After this, she returns to the club with everything mended between her and her friends. 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 seem to get along quite nicely, though Yui sometimes finds Hachiman's rotten personality and distorted views annoying or misguided. In return, he is frequently frustrated with her upbeat attitude and doesn't hesitate at times to put her down. In the light novel, Yui even offered to organize and celebrate Hachiman's birthday party with Yukino, Saika and Komachi, but Hachiman turned down her offer.
It is heavily hinted that Yui has romantic feelings for Hachiman though she appears not act on it. It is unknown exactly how he feels about her however, there have been hints that Hachiman knows about her feelings for him, due to studying people. For the most part, he might be unwilling to acknowledge her feelings are real because of his past mistake and unfortunate luck.
Hachiman ended up accompanying Yui to the end of summer fireworks festival, due Komachi's meddling. 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 seemed like she was going 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. Hachiman was unsurprised by her attempted confession, which is another sign of his awareness of her feelings.
During the Culture Festival, Yui offered Honey Toast to Hachiman which she herself shared with him at the reception table of their class. When Hachiman wanted to pay for the honey toast, She asked him to take her out to Pasela (Karaoke Chain). But Hachiman requested time to think about it, to which Yui agrees happily.
Yui paired up with Hachiman during their field trip to Kyoto. After Hachiman's actions during Tobe's request, Yui tearfully asks why he can't understand others pain, while also hinting that she likes him. Things are eventually cleared up after Komachi has him formally apologize to the girls.
Later, they appeared to have grown close as both of them have developed the habit of walking to the clubroom together from class.
Yui begins to see the romantic tension between Yukino and Hachiman and suspects they have feelings for each other and appears to compete with Yukino for Hachiman.
In episode 13 season 2, Yui finally plans out the date Hachiman owes her, but she invited Yukino along. Yui requests that their status quo 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.
Hachiman once paired up with Saika for tennis. Saika also asked Hachiman personally to join the Tennis Club to help raise their strength. Hachiman has an attraction towards Saika but reminds himself of the latter's gender. 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 Hachiman denies they are friends due to Yoshiteru's eccentric personality and weird habits.
Yoshiteru trusts Hachiman enough to share with him his ambitions of becoming a writer, and Hachiman cares 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.
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 less 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.
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".
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 and even befriends him. The interaction between Saki and Hachiman is focused on more in the Light Novel than in 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 if he has ever put thought into them.
In the haunted house during the field trip,she was seen clinging to Hachiman's blazer. 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 popular kids, Ebina calls Hachiman "Hikitani-kun". It's eventually hinted 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. She seems to like the idea of Hayama 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 .
After Iroha was elected, she 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.
Eventually, Hachiman starts to see through Iroha's lively and air-headed persona, and recognizes her as a sly and smart person. He also notices her lack of confidence and vulnerability. Being the 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, and 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 shocked 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.
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 treated badly by people as nobody put trash on his desk anymore nor tried picking on him. 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 seen as a nobody, he gained acknowledgement for being the student who hurt the feelings of Minami Sagami. Some know the real reason and praised him for it while others give him angry glares for his assumed cruelty but nobody picked on him nor did they mistreat him as before. Fortunately, this blows over as time passes, especially after the trip to Kyoto.
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). Rumia 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 fond of Hachiman and calls him Haa-chan. Mostly they play when ever they meet. In light novel Keika offered Hachiman a bag of Valentine chocolates and kept on clinging to 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 jaded view on women just as they have on him.
After middle school, Hachiman has tried 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 wants nothing to do with her, an intrigued Haruno meddle and gets 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 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 know him very well back then. Kaori brings 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.