At this point, his observations were not used for ill, rather a simple hobby, but slowly it was turning more and more into an obsession. His chaotic life changed after meeting fellow middle school student, Shinra, who immediately assessed Izaya's personality and tried to convince Izaya into creating a biology club.
At first, he declined his offer and after that, he continued living the same life he had in elementary school, while keeping an eye on the human called Kishitani Shinra, but one day he suddenly understood: Shinra was his opposite because unlike Izaya, he had no interest at all in human beings. This confused Izaya who eventually agreed to become the Vice President of Shinra's club so he could study him more closely.
When a club expo was scheduled, Shinra left their presentation entirely in Izaya's hands and, much to Shinra's surprise, Izaya turned the whole club into a gambling ring with one of the other members, Nakura, serving as Izaya's business partner. Shinra tells Izaya to stop but gets brushed off each time. One day, after making a bad bet, Nakura comes in brandishing a knife and threatens Izaya to give back all the money he lost. When Izaya refused, Shinra jumped in the way of the knife at the last minute. It is then that Izaya realizes he is extremely jealous of Shinra because of his ability to separate himself from the world because of his love for Celty. Izaya then asks Shinra to tell everyone that Izaya himself was the attacker and promises to make Nakura pay for as long as possible for what he did. After the incident, Izaya is taken into protective custody and, from then on, continues to create an infamous reputation.
He was later enrolled in Raijin Academy High School with Shizuo, Shinra and Kadota; although, Izaya rarely attended class. He shares a passionate hatred for Shizuo and from nearly the moment they met they tried to kill each other. Izaya claims Shizuo is the only human he does not love and wouldn't mind seeing him dead. Shizuo tries to kill him every time they meet on the street, meaning Izaya often finds random vending machines, trash cans and other large objects flying straight at him. Shizuo finds him untrustworthy, saying whenever there is trouble, "99% of the time you're (Izaya) behind it." Izaya had often framed Shizuo for crimes he didn't commit, causing him no end of trouble. During one of their more hectic confrontations, Kine, an high ranking member of the Awakusu was caught in the crossfire. Kine managed to dissolve the conflict but took an interest in Izaya who was just starting out as in information broker at the time. Through Kine, Izaya met many of his first clients in the Yakuza and was his official contact with the Awakusu.