The theatre is crowded and hot, with a lower-class audience. The play begins and Sibyl makes her entrance. Lord Henry acknowledges that she is beautiful. But then Sibyl performs very poorly, and Henry and Basil are disappointed. Sibyl gets even worse in the second act; she speaks as if the words have no meaning to her. The audience starts to lose interest in the play, and there are hisses at the end of the act. Dorian admits that Sibyl is acting badly, but insists that the previous evening, she was superb. Henry and Basil leave. The last act is played to an almost empty theater. When Dorian goes backstage, he finds Sibyl very happy, even though she knows she acted badly. She explains that since she met him, she has learned what real love is, and now the characters in the play seem hollow and silly. Everything about it is false. Dorian is disillusioned by her words, which destroy his love for her. He loved her because she was able to bring great art to life. Now he thinks she is only shallow and stupid. He says he will never see her again. Sibyl is shattered. She begs him not to leave her, but he takes no notice and leaves the theater. He walks around London all night and returns home at dawn. His eye falls on the portrait of himself that Basil had presented him with. He notices that the expression on the face seemed to have changed, and taken on a cruel look around the mouth. He remembers how he had wished that he could remain eternally youthful and unblemished while the portrait grew old and reflected all his sins. He now realizes with alarm that the portrait holds the secret of his life. He resolves not to sin any more, to resist Lord Henrys influence. He decides to go back to Sibyl and try to make amends.
It is past noon when he awakes. There is a letter from Henry, hand delivered that morning, but Dorian does not open it. He has breakfast and feels perfectly happy until he remembers the picture. He wonders whether it really has changed, but one glance at it confirms that it has. He realizes he has been cruel to Sibyl, and in the afternoon he writes her a passionate letter, begging her forgiveness. Henry arrives, concerned about how Dorian has reacted to his letter. He does not know that Dorian has not read it. When Dorian says he is going to marry Sibyl, Henry realizes he has not read the letter, which informed Dorian that Sibyl was dead. She killed herself by drinking acid. Dorian feels as if he is guilty of murder, but soon decides that he is not upset by it. He thinks she was selfish to commit suicide. Henry tells him that his marriage to Sibyl would have been an absolute failure.
Dorian sees the whole incident as like a Greek tragedy, something he has witnessed but which has not hurt him in any way. Henry confirms that this is the right attitude (although he uses Jacobean drama as an example) and tells him not to shed any tears over Sibyl. He says she was not as real as the characters in great art.
After he goes home, Dorian checks to see that the picture has not changed again. It has not, but Dorian knows that it will in the future, as he lives out his life dedicated to pleasure and passion. For a moment he thinks of praying that the strange relationship between himself and the picture might change. But then he realizes there will be pleasure in watching it, since the picture will reveal to him the state of his own soul. That evening he goes to the opera with Henry.
Basil calls on Dorian, wanting to commiserate with him over Sibyls death. But Dorian tells him not to talk about it. Basil is shocked at his callous attitude. He blames it on Henrys influence. But Dorian explains that he has simply grown up now. He has new passions, new thoughts and new ideas. Basil agrees not to speak of Sibyls death again. He then says he wants Dorian to sit for him again, and he asks to see the portrait he gave him, which Dorian has hidden behind a screen. Dorian angrily refuses to let him see it. Basil protests, saying he plans to exhibit the picture in Paris in the autumn. Dorian reminds him that he promised he would never exhibit it. Basil explains why he made this promise. He confesses to Dorian that he has had an extraordinary influence over him. He worshiped Dorian because he saw in him the embodiment of the image of perfection, the memory of which the artist holds in his mind, and which transfigures everything in the world. He thought that the picture of Dorian he painted revealed too much of his personal feelings about his subject, and he feared others would discover his secret, which he had not admitted to anyone. But now he thinks that the painting does not reveal his feelings. He believes that art conceals more than it reveals, so he feels free to exhibit it. Dorian thinks this a strange confession, but he still does not allow Basil to see the picture. After Basil leaves, Dorian decides he must hide the picture.
In these chapters Dorian takes the first steps toward his own corruption. Not only does he behave in a cruel way towards Sibyl, he soon learns to reject any remorse over it. He tries to have an attitude of detachment to his experience, drawing on Henrys ideal that one should be spectator of ones life. The ideal is to maintain an aesthetic distance at the same time that one is experiencing something to the full. This is the experience that art produces, and Dorian want to replicate this in life. He rejects Sibyl because she is valuable only as only as long as she is a vessel for pure art. In herself, she is nothing; she cannot transfigure life for Dorian, and as an ordinary human being she is not worth any consideration. Sibyls mistake in his eyes is to reject art for life. As a result, she makes herself vulnerable and suffers emotional pain and physical death.
Cruelty and selfishness has now become a part of Dorians nature, perhaps under the influence of Henry, although it may have been part of his character before, since in chapter 1 Basil complains that sometimes Dorian is charming but at other times he can be cruel and he seems to enjoy causing Basil pain.
The views expressed by Lord Henry are clarified in Wildes essay “The Critic as Artist,” in which he wrote, “Art does not hurt us. The tears that we shed at a play are a type of the exquisite sterile emotions that it is the function of Art to awaken. We weep, but we are not wounded. We grieve, but our grief is not bitter.” In other words, art is superior to life, which does hurt us. Life lacks the form of art, as Wilde argues earlier in the same essay: “Its catastrophes happen in the wrong way and to the wrong people. There is a grotesque horror about its comedies, and its tragedies seem to culminate in farce. One is always wounded when one approaches it.”
Chapter 9 reveals the difference between the amoral Henry and Basil, the artist. Basil does not believe that the artist, or anyone else, can absolve themselves of moral responsibilities, which is why he is horrified by Dorians cold reaction to Sibyls death.