Tobe is friendly with everyone, as he makes conversation with anyone including Hachiman regardless of clique. He was mentioned to have good relation with his clubmates, senpai and Kohai
Clique EditTobe belongs to popular Hayama's clique. He is also friends with Ooka, and Yamato, along with Yumiko Miura, Yui Yuigahama and Hina Ebina, with whom he often hangs out. They seems to spend their outing such as new year celeberation, Bowling, Chiba summer camp volunteer and also in teaming for Work place visit, Class play for cultural, Chiba visit, Christmas collaboration event's etc. Tobe seems to be present, almost in every outing while Ooka and yamato seem to absent in some.
They also gave a great contribution in the class play for the cultural festival and also in the closing ceremony with a concert. Most of the members of the clique are against Tobe's confession to Hina, to save their status quo which Tobe is completely unaware.
Hachiman felt that they appear to be close for outsider and only friends in face value, which is proven more than once such as the false chain message incident. Hachiman also notices that their intention for helping Tobe to confess were not of pure concern or care but for fun which Tobe himself noticed.
The boys are mentioned to be noisy, and dominate in the class, trying to impress girls. Tobe is mentioned to be the noisy one in the group which is seconded by Yui. Tobe hangs out more often with the clique while Ooka or Yamato were absent in summer camp and Destiny land. All the three are members of various sports club. The trio also indirectly asked the girls for valentine chocolate.
She is the girl whom Tobe harboured feelings for. Tobe's feelings for Hina is mentioned at times during the Chiba summer camp. There were hints in Volume 6, that he tried his best to impress, and at times during their first hurdle of the class play, trying to stand beside her but only to be avoided.
It was later revealed in the light novel that Hina knows of Kakeru's feelings for her, but does not want to engage in a relationship at the current time due to her lack of confidence and strange personality, and thus indirectly requested help from Hachiman to help her maintain the status quo, which Hachiman succeeded in.
But even so, Tobe isn't ready to give up on her.In Episode 12 of season 2, Hina participated in a pre-valentine collaboration event where she made some valentine chocolate that were given to Tobe. Hachiman feels that they are getting a little closer then before and hopes for progress. Where they stand now is currently unknown.
Yui seems to have friendly relations with Tobe. Tobe calls Yui by her first name while Yui call him by a nick name, Tobecchi. Yui agrees that Tobe is a noisy person but doen't seem to be bothered by it. Yui doesn't hesitate to show her anger towards Tobe when he gave a negative comment about Hachiman in the service club. However Yui persuaded the service club to help Tobe and set schemes of her own to get Tobe and Hina closer.
Once in summer camp, Tobe mentioned Yui was cute but an air head which irritated Hachiman, as he feels that Tobe isn't that much different to be criticising Yui.
Yumiko and Tobe have a normal conversation. There are hints of Yumiko helping Tobe's love in the past without their knowledge but predicted the result and backdown. Even though she dominates him with some respect as a fellow student.
Tobe is the first person to mistakenly address him as Hikitani. It becomes an informal nickname, which results in his clique members calling Hachiman the same. After the Chiba Village summer camp incident, he started to have a very negative opinion of Hachiman, and felt that he is a seriously terrible person. However, when a girl told him of Hachiman supposedly badmouthing Sagami, he defended Hachiman at some extent by saying that he can't have saying such thing.
At the end of the cultural festival, he shared his opinion with everyone in earshot. He even made fun of Hachiman by referring to 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. He trusts Hachiman's toughness is due to indifference towards him while Ooka and Yamato's encouragement for his confession is because they think it's fun.
After the field trip Tobe casually talks to Hachiman in a friendlier manner than before, hinting that all his negative opinions of him have vanished. But he still believes Hachiman's surname was Hikitani and even addressed him by that name, much to the latter's annoyance.
The Light novel shows a 180 degree change of Tobe towards Hachiman more clearly than the anime version, this can be seen by their conversation which is also noted by Hina which she mentions during her request to the service club. Tobe also tried to socialise Hachiman by inviting him to play in the Kyoto trip but was declined by Hachiman not before understanding his intention. Hachiman also mentally agrees with Hayama's opinion of Tobe, after knowing him better, but still feels him to be annoying. Hachiman also gives a good conduct of Tobe to Hina, when she came to thank him.
Briefly on the bullet train to Kyoto, Hina forces Saki to sit right across from her and right next to Saki. Yui later tells Hachiman that Saki was everything but happy to sit next to Tobe, and Tobe himself was very nervous sitting next to Saki, and is scared of her.
Minami holds up a façade to hide her arrogance with innocence, and it is implied that Tobe is unable to see through it, as he recommended her to be the female representative for the cultural festival after Hayato suggested that the representative should be "someone who can show leadership", and also feels proud, when his suggestion was agreed by Hayato. Minami, however, doesn't appear to view Tobe as much, as she is seen bossing around Tobe, Ooka, and Yamato even though they appear to be working hard.
When he heard of the rooftop incident, like most of his classmates he was sympathetic towards her and believes that Hachiman was "seriously terrible" and something not unlike the rooftop incident also happened during summer. He was mentioned to have a conversation with Minami's cliquein Volume 6.5 and even joined in on their gossip of Hachiman.