A month later, Dorian pays a visit to Henry, finding his wife at home. She is pleased to meet the man with whom her husband has become so preoccupied. After Dorian's comment that one is obligated to engage in conversation when bad music is being performed, she remarks that "that is one of Harry's views...I always hear Harry's views from his friends, that is the only way I get to know them." Henry (or "Harry") arrives, and his wife exits. Henry tells Dorian never to marry a woman as sentimental as his wife, a trait which he blames on the fairness of her hair.
Dorian delivers the news that he has come to share: he is in love with a girl named Sibyl Vane. She is an actress who plays all of the young leading female roles at a theater devoted solely to Shakespeare's works. The theater and the rest of the cast are of very poor quality, but Sibyl is apparently a brilliant actress and stunningly beautiful. Dorian went backstage to meet her after the third performance he had attended, and found her to be completely unaware of her own skill, seemingly unable to separate real life from that of the stage. He tells Henry that she prefers to call him "Prince Charming," because, as Dorian says, "She regarded me merely as a person in a play. She knows nothing of life." This purity and naivete is indescribably charming to Dorian: he has fallen madly in love, and tells Henry that he worships Sibyl and that she is the only thing that matters to him.
Dorian convinces Henry to come with him to see her play Juliet in the next day's production. Henry says that he will invite Basil. At the mention of the painter's name, Dorian remarks that he feels guilty for having ignored the painter for several weeks, since he appreciates the masterful portrait despite being "a little jealous of the picture for being a whole month younger than I am."
The conversation turns towards the character of artists, and Henry insists that the better the artist, the duller his personality, and that only truly terrible artists are worth spending time with. Dorian eventually takes his leave. Later that night, Henry returns home to find a telegram from Dorian informing him that he and Sibyl are engaged to be married.
This chapter describes a key moment in the development of Dorian's personality. Henry is not jealous of Dorian's fascination with another person, but pays careful attention to Dorian's impression of his own emotional state. Recognizing his influence at work on the boy brings "a gleam of pleasure into his brown agate eyes"; he is like an artist proudly admiring his work. Henry's views are elucidated by the statement that "a complex personality...was indeed, in its way, a real work of art." Henry's beliefs are delivered in the voice of the narrator; this technique, called "free indirect discourse", is one that Wilde frequently used.
The nature of Dorian's love reflects Henry's devotion to life as art. Sibyl is described as almost completely devoid of her own personality, and only able to behave as if she is in a play. Dorian is in love with the characters she plays, with her talent, and with her beauty, but not with her. He values everything superficial about her, as is revealed when she tries to show her true self to him.
Early in their conversation, after telling Henry how much he treasures his words and trusts his judgment, Dorian states, "If ever I did a crime I would confess it to you. You would understand me." This boldly foreshadows later events in the novel, and is also an indication of the commencement of Dorian's degradation. The young man that was innocent and good-hearted only a month before now freely considers criminal actions for the sake of having a new sensation, without giving a single thought to the possibility of a guilty conscience.
Dorian criticizes Sibyl for treating him like a person in a play, but is blind to the fact that he has fallen in love with the characters she plays, and hardly even knows the girl herself. Dorian has begun to whole-heartedly devote himself to artistic ideals, mistakenly assuming that they are his reality. Indeed, when Sibyl begins to show a glimmer of the person behind her characters, Dorian's reaction is not very pleasant. Earlier, however, he doesn't even hesitate to propose to a girl he hardly knows; a testament to his misguided devotion to artistry and artifice.
Henry realizes the error of Dorian's ways, but instead of pointing them out for the sake of his friend's well-being, he anticipates the fun he will have observing the repercussions. Dorian's blossoming self-centeredness is a successful manifestation of Henry's influence. Interestingly, this is the first chapter in which Dorian actually has more dialogue than Henry. Until this point, we have witnessed Dorian's reactions only through Henry's eyes, and through narrative comments. Dorian only actually begins to take the spotlight once his corruption is underway.