Shiroe's various relationships in the Log Horizon series.
Shiroe and Naotsugu have a strong bond and deep and caring respect for one another, having known each other through the Debauchery Tea Party. Because of their four-year bond, Shiroe understands that Naotsugu can defend himself unassisted.
Although they are opposites when it comes to personality, with Shiroe being quiet and reserved and Naotsugu being loud and outgoing, the two mesh together well. The first time they met, Naotsugu saw Shiroe drinking tea, and his innocuous yet factually incorrect remark led Shiroe to go on a lecture about the difference between oolong and black tea, which then led to a discussion about the economics of tea and the condition of the tea market. From then on, their friendship flourished.
In volume 9's Debauchery Tea Party relationship chart, it states that Shiroe and Naotsugu are close friends.
Akatsuki is one of the founding members of Log Horizon. She acts as his ninja, calling him lord and following his requests. The two had been acquainted with each other when Shiroe was with her party on a quest, and had partied together several times prior to the Catastrophe.
Several days after the Catastrophe, she found Shiroe and Naotsugu by chance, and requested an Appearance Reset Potion to change her avatar. She has since sworn loyalty to him and becomes closer, developing feelings for him in the process. She admires his intelligence, mature personality, kind nature, and leadership skills and is loyal and would do anything for him. Akatsuki also competes with Minori over Shiroe's love multiple times while Shiroe himself is completely blind to it.
Shiroe's exact feelings for her remain unknown but he seems closest to her out of all of the Log Horizon members (besides Naotsugu and Nyanta) and deeply cares for her. However, he finds her intense roleplaying to be a bit unnerving, and tries involving her in situations where he isn't around (such as acting as Rayneshia's bodyguard as a member of the Watermaple Consulate tea parties) so that she can't use him as an excuse to avoid interacting with others.
Shiroe seems to have a large degree of respect for Nyanta and, like Naotsugu, they've known one another since the Tea Party days. Nyanta and Shiroe work exceptionally well together, with Shiroe using Thorn Bind Hostage to allow Nyanta to cause immense damage with each of his blows.
At times, Nyanta serves as Shiroe's mentor or confidant. Even in the Tea Party, Nyanta was the group's oldest member, and is known for his wisdom.
In the Tea Party relationship chart, Nyanta says that Shiroe is a "good kid," but Shiroe does not comment back.
Shiroe helped Minori along with her younger twin brother Tohya when they first started out in the game, even though it was against his usual nature, because he understood they weren't trying to use him as a tool and truly wanted to enjoy the game. He became close to them, but in the chaos of the Catastrophe, failed to contact them. Although he saw them with another group of people afterwards and believed they were safe, he still felt guilty for not calling them sooner.
Upon learning from Maryelle about the existence of Hamelin, and piecing together that Minori and Tohya were tricked into joining, he decides to take a stand.
Minori began taking under his wing and began to develop feelings for him. Shiroe does not see her in a romantic light and remains oblivious (as he is with all of the other females' feelings for him) but he treats her like a younger sister and is fond of her. That still doesn't stop her from being competitive with Akatsuki over who Shiroe loves.
Tetora and Shiroe are on good terms with one another. He currently knows her secret about being a boy in real life (something that, in the light novel, nobody else knows). They both trust each others' abilities, although Tetora occasionally causes Shiroe some trouble by instigating Akatsuki and Minori's competitions over him (something seen only in the anime).
Maryelle and Shiroe have had a good relationship even before the Catastrophe. Even before becoming a guild master, Shiroe got along with Maryelle and admires her for being a female guild master. The two get along well as great friends and she was the one to tell him of the situation after the Apocalypse. She and Shiroe often collaborate the most together out of all the guilds and even seem to be the closest of the guild masters, though the two never extend beyond a platonic level. She also trusts his political and analytical skills, though becomes afraid of him when he becomes "the Villain in Glasses" persona. Shiroe, in turn, trusts her a great deal.
In the light novel, he admires her inspirational abilities, and states that the dead would rise again if she asked. (In the anime, he instead calls her "spacey".)
Henrietta is a member of the Crescent Moon Alliance, one of Log Horizon's allies. She is similar to Shiroe in that they are very intelligent and are often called villains in glasses (though Henrietta far less than Shiroe) due to their cunning minds and manipulative tendencies, making them the masterminds of their guilds (though Maryelle is the guild master of Crescent Moon). She has feelings for him but Shiroe remains oblivious and she believes that she is not good enough for him and wishes both Minori and Akatsuki luck as she believes they would be better for him. The two still remain on good terms regardless and at one point even acted like newlyweds, as Henrietta still worries for his health because he has a tendency to push himself too far.
As it turns out, Henrietta's father was much like Shiroe, and Henrietta adopted her mother's taste for hardworking men.
Shiroe and Krusty are friends and appear to be on good terms with each other. Krusty doesn't believe Shiroe to be much of a strategist and more a gambler; Krusty once comments to Isaac that Shiroe is a cursed sword that is waiting to be drawn.
Isaac and Shiroe are confident in each others' abilities, as Shiroe had occasionally worked as a mercenary with the Black Sword Knights. In the past, Isaac also tried recruiting him, but was always turned down.
Soujiro and Shiroe are on good terms and were both in the Debauchery Tea Party. When the Tea Party disbanded, Soujiro asked Shiroe to join the then-newly-formed West Wind Brigade, but was turned down, causing Souji to think that Shiroe hated him. As a result, there was little communication between the two until the plan to form the Round Table Alliance, where Shiroe requested Souji's help and cleared up the misunderstanding. Shiroe and Soujiro seem to have a "senpai, kohai" relationship and Soujiro has a deep respect for Shiroe.
At times, Shiroe is envious of Soujiro's harem, and even sends him over to Kanako's Cake Shop after Shiroe's disastrous experience there. Upon Soujiro's exploits, which ended with the place running out of cakes, Shiroe is shocked beyond words. However, he then realizes that he could use Souji's extensive harem (of which Souji was oblivious to) in controlling the Libra Festival.
Nureha has a one-sided obsession with Shiroe because he complimented her playing style, and she immediately developed feelings for him, seeing him as the first person to notice and accept her. However, Shiroe does not remember this, apologizing to her and stating that he can't return her feelings. She tries to entice him to joining her and leaving his guild by offering information on a way to go back to the real world but he refuses, stating he will remain loyal to his guild and the people who have supported him. Upset by this, she leaves to brood in her palace back in Minami.
Indicus uses Nureha's obsession with Shiroe and her own low self-esteem into psychologically abusing Nureha into doing her bidding. However, Nureha says to herself that the reason she partnered with Indicus was not only to accomplish her own goals of making a place where she belonged, but also because of Shiroe's promise of how he would be more useful to her as her enemy than as her friend, and that he will be her enemy whenever she finds reason.
While Shiroe finds Indicus to be capable, she has a very low opinion of him (as she does with almost all the other Tea Party members aside from Kanami), stating that he's "such a show-off!". After the Catastrophe, she denounces him as a traitor in Nureha's presence, and verbally abuses her by stating that he would want nothing to do with her. She also looks down on his skills, thinking that he wouldn't be able to disrupt her plans.
Shiroe and Kazuhiko are on much better terms than he is with Indicus. He views Kazuhiko to be skilled, while Kazuhiko finds him trustworthy.
Demiqas and Shiroe has had a bad relationship ever since their first encounter. When they met again in the Abyssal Shaft Raid Party they weren't pleased to see each other. Over the course of the raid, Shiroe continued refusing to call Demiqas by his real name, while Demiqas believed that Shiroe was looking down on him by buffing him.
However, Demiqas was well aware of Shiroe's capabilities, causing him to kick Shiroe out of Tarutauruga of Fourth Prison's attack in a futile attempt to save Shiroe from dying when the three raid bosses gang up on the raid party. Afterwards, during the raid party's second attempt, Demiqas keeps the plan from falling apart when Ruseato of Seven Prison damages itself to produce Shadow Warriors by kiting the Shadow Warriors while dragging Shiroe to their end goal. There, Demiqas tells Shiroe to say his name, which makes Shiroe realize how disrespectful he had been towards him. Although the two agree to disagree, they have a new-found respect for each other by the end of the raid.
Rayneshia views Shiroe as a manipulative monster to go with Krusty's mind-reading monster. As a result of her speech in Akiba and the situation with Marves, she doesn't have a very high opinion, even though she recognizes his abilities.
On Shiroe's part, he acknowledges that it's because of her decision to plead with the Adventurers personally that both the nobles and the Round Table Alliance was saved.
Kanami was the old leader of the Debauchery Tea Party who named Shiroe as her "bus guide," "tour guide," or strategist. Sometimes, when Shiroe doubts his abilities, he thinks back to Kanami and her words about enjoying the adventure. While his feelings for her remain unclear, it is obvious he held her in high regard, stating that he learned from her. However, he admits that her tendency to drag everyone around and forget important items for quests could get tiring after a while.
Kanami, true to form, calls Shiroe "cute" (as she does with just about everyone and everything) and has faith in his ability to figure things out. She tells Leonardo and Elias Hackblade that she would figure out the answers to this "great adventure" if she found Shiroe.
On the Tea Party relationship chart, Shiroe is stated to admire her, while she sees him as a "capable bus guide." Even in the present, he judges most of the other sex's actions by comparing them to Kanami's; for example, he didn't refuse either Akatsuki's or Minori's invitations to the cake date because he figured that if all women were as willful as Kanami, then there was no point in arguing back.
Roe2 is Shiroe's alternate character avatar. Although the two have yet to meet face-to-face, Roe2 (or rather, the Traveler inhabiting her body) sides with Shiroe and does everything in her power to aid his cause.