In Oscar Wilde’s The Picture of Dorian Gray, James Vane is the younger brother of Sibyl Vane who was an up and coming actress. That changed the day Dorian Gray proposed to Sibyl and showed her the possibilities the world had. This lead Sibyl to hate acting and she gave the worse performance of her life, and since Dorian only fell in love with Sibyl for her acting he ended his relationship with her and said he would never talk to her again. This moment of hope in the future followed by complete and utter hopelessness caused Sibyl to commit suicide.
This led James to seek out the man who caused his sister’s suicide and avenge her death. The first problem was the only thing James knew about Dorian was that Sibyl called Dorian Prince Charming. The second problem is when James finally found Dorian after years of searching James told Dorian his entire story and plan to murder Dorian like any cliché villain would. This let Dorian find away to convince James that Dorian never knew Sibyl. James’s third mistake was showing up at Dorian’s party after learning that Dorian was lying. This made Dorian on edge and more cautious about being alone. James’s fourth and final mistake was that he ran into the field Dorian’s friends were hunting in causing James to get shot and die. There was a series of mistakes that ruined James’s revenge, but in the end it was in a sense fulfilled as Dorian accidentally killed himself later.