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Celty Sturlson[]

Main article: Celty Sturluson
I'm not going to do anything. I'll be with Shinra to the end. ...I don't want to be separated from him. I realized this stronger than ever when he recently got hurt. I can't forgive those who hurt him, and I'm willing to play along with your distasteful work to get even. You see, Shinra does love me... and I love him, too.

Celty Sturluson, Volume 9, Chapter 4

Celty and Shinra official art

Shinra first met Celty after finding her hiding in the cargo hold of a ship that he and his father were taking to Japan. At this point in time, what Shinra felt toward her was merely a sense of awe and wonder. He continued to remain interested in his supernatural roommate as he grew up, and this curiosity eventually evolved into love. Celty, on the other hand, remained indifferent toward Shinra for most of his life and even seemed to find him detestable at times. However, as she spent more time around humans and found her own emotions and desires becoming more aligned with theirs, she began to reciprocate Shinra's feelings.

In the beginning, the main conflict in their relationship was their differing opinions on Celty's head. While Celty wanted to locate her head, and by extension, her memories, at all costs, Shinra repeatedly attempts to dissuade her from continuing her search, occasionally disregarding her feelings on the matter. This unsurprisingly caused a few sparks to fly between them and it reaches its peak after Celty realizes Shinra had kept her head's location from her the entire time and that he had altered Mika's face to look like hers. The two have since reconciled and, while Celty does still occasionally continue her search, she doesn't feel as much urgency as she did before.

Currently, the only real source of conflict between the two, as stated in the previous section, is Shinra's over-obsessiveness toward her. However, considering that Celty has known Shinra since he was child, she developed a tolerance for this long before they made their relationship official.

S1 E12 Celty and Shinra

Celty hugs Shinra

At the end of the Mika Harima arc, Shinra displays his desire to remain with Celty no matter what, freely admitting to intentionally kept the location of her head from her because he feared that if she reclaimed it, she would leave him. Celty begins to analyze her own feelings for Shinra, and the two soon after enter into an official relationship.

Volumes 5 and 6 of the light novels had several sections narrated by Shinra titled "The Black Market Doctor Gets Sappy." As the title implies, each and every one of them features Shinra rambling on about something and somehow steering the subject over to his love for Celty. In a flashback in the eighth light novel, Shinra was shown to be protective over Celty to the point where he threatened Aoba, who was trying to befriend Celty, because he sensed Aoba's ulterior motives.

Izaya Orihara[]

Main article: Izaya Orihara
Izaya Meeting Shinra Durarara!!x9 LN

Izaya agrees to help fund Shinra's biology club

Their friendship can best be described as "bizarre." Izaya and Shinra were classmates in Raijin Middle School. On the first day of school, Shinra approached Izaya to invite him to found a Biology Club, for his interest being "human observation." Izaya at first rejects the idea, but becomes intrigued with Shinra as a person. After doing some questioning around with other students, Izaya realizes that Shinra is the opposite of him—having no interest in humans, unlike himself. Wanting to know why Shinra held such disinterest towards humans, Izaya finally agrees to join as the Vice President of the club.

The Biology club is created as merely a front: Shinra uses it for the excuse to have a friend (thus earning the approval of his 'beloved'), while Izaya uses it for Baseball gambling with other students. When Shinra finds out about the gambling, he tries to dissuade Izaya out of it. Nakura, a member of the gambling ring, desperate to get the money back that he'd lost, suddenly comes in to attack Izaya, but Shinra jumps in between and ends up getting stabbed as a result. Izaya takes the blame for the incident and uses it to continually blackmail Nakura through the series.

Izaya attributes this event as something that helped shaped his personality. He'd felt envy toward his friend who seemed to be "watching humans from a different plane." They later both attend Raijin High school, where Izaya meets Shinra's elementary school friend, Shizuo, and begins a mortal rivalry. After High school, Izaya is seen occasionally hanging out with Shinra at Raira University, though the latter is not a student.

Currently, Izaya believes he isn't an important friend to Shinra, as he treats Celty as his top priority in life. An example of this is when Izaya tried to contact Shinra over the phone while at the hospital. Shinra hung up on him because he was too busy trying to enjoy his date with Celty (especially after having been continually interrupted by other callers). As a result, when it was Shinra's turn to be hospitalized, Izaya decided to also give him the cold shoulder.

Nevertheless, at various points in the novels, it is revealed that Shinra is the only person that Izaya actually considers a friend, and not just one of his "humans." Kisuke Adabashi, the man who injured Shinra, was eventually caught by Izaya's gang and kept confined at his apartment until he escaped by the series' end. Likewise, Shinra views Izaya as one of his only friends, and constantly defends him in front of Shizuo and Celty, even though he knows that "there's not a single ounce of goodness in him."

Shinra is Izaya's opposite. While Izaya claims to "love all humans," Shinra does not possess ANY feelings or interests towards them at all. Being too absorbed on Celty, who is a non-human, he practically lives in a different world. Despite his lack of interest in humans, Izaya thinks that Shinra's assessment of them is accurate. He was the first person to have seen through Izaya's nature, yet they still remained on friendly terms (unlike other people who express disgust toward Izaya once they see through him). Yet because Shinra is able to remain objective toward all humans—neither liking nor disliking them, regardless of how bad or good they are—it is difficult to tell what he really feels as far as 'friendship.' Moreover, Izaya claims to see all humans equally, whether they're his friends or his family or neither.

Although there's been no contact between them since Izaya vanished from Ikebukuro, they both continue to regard each other as "friends." Byakuyamaru Natsugawara, who happens to be acquainted with the Kishitanis, urged Izaya to go visit Shinra after such a long time at the end of "A Standing Ovation" novel, to which Izaya replied, "I'll see about that, if I have the time." Kazane Kinomiya, Shinra's half-sister from a different father whom has had dealings with Izaya in the past, likewise has expressed a desire for Izaya and her brother to meet again.

Shizuo Heiwajima[]

Main article: Shizuo Heiwajima

They were classmates in elementary school, where Shizuo's abnormal strength earned Shinra's attention, and he constantly asks Shizuo to let him cut him open. They end up attending separate middle schools, but meet once again in Raijin High School, still pestering him about at least getting a blood sample. Though there are many times when Shinra is nearly damaged by Shizuo, it doesn't seem to deter the other from continuing to annoy him. Even after high school, Shizuo repeatedly barges into Shinra's apartment to make uses of his "doctor" services, either to patch himself up or someone else. Shinra will not refuse a request from Shizuo's brother Kasuka, out of fear Shizuo will beat him up, but admits he is actually quite grateful towards Shizuo for looking out for Celty. When Shizuo is accused of killing several members of the Awakusu, Shinra is able to help out by smoothing things over with them, thus earning a rare thank you from Shizuo.

Shingen Kishitani[]

Main article: Shingen Kishitani

Shinra and his father Shingen have a fairly stable relationship. When he was a child his father would let Shinra join him in performing surgeries, including the one where he dissected Celty. Shingen believed that Shinra has always been a "sicko" since besides his love for Celty, he believes Shinra enjoyed the past dissections "too much". Beside that he genuinely loves Shinra. Shingen cut Celty's head off and sold Saika's sword off to Anri's parents in order to protect Shinra from Namie's grandfather who threatened to kill Shinra if he didn't. When he discovers that Shinra was beaten up by Ruri's stalker, and Seitarou could have prevented it, Shingen doesn't hesitate to call Seitarou and warn him that he'll "smash his face" for what he did. He even goes to the dojo and asks Eijirou to teach him the deadly punch he knows so he can go get back at Seitarou.