Lord Henry, the next day, visits his uncle, Lord Fermor to gain information about Dorian's background. He learns that Dorian is the son of a low level officer, in a foot regiment and his mother is Lady Margaret Devereux. His mother's father is Lord Kelso, who had Dorian's father killed and a year after his father's death, his mother died. This left Dorian to be raised by his heartless grandfather, Lord Kelso. Dorian inherited his beauty from his mother and his grandfather kept him isolated, which explains his innocence to the ways of the world.

Lord Henry, after gleaning this information from his uncle, proceeds to a lunch engagement with his aunt and her friends. Also at the lunch is Dorian, which is the real reason Lord Henry has accepted the invitation. There is an eclectic mix of people at the party, ranging from an author to a member of parliament. They have a fine time exploring the topic of American women who have traveled to England to find husbands. The women at the lunch find this practice unsettling, because how are the English women supposed to find husbands, if the American women are snatching up the respectable English men. They also find Americans rather common, which is to say they do not live up to the social standards of English society.

Lord Henry is in a philosophical mood and tells one of the ladies the way to stay young is to repeat the mistakes she made in her youth. He feels that using common sense is the kiss of death, but a person seldom regrets the mistakes they make.

All during the lunch, Dorian is sitting at the table looking at Lord Henry with a look of fascination. He wants to spend the rest of the day with him, just to hear him speak. He wants to hear the ideas Lord Henry has and is willing to give up his day with Basil, to spend time with him.

A month later Dorian visits Lord Henry at his home. He meets Lord Henry's wife, Victoria, who is charming and also interested in Dorian, because he has become so important to her husband. Lord Henry is using Dorian as a subject to study how a human, who has been sheltered most of his life, reacts to being suddenly exposed to new thoughts, ideas, and experiences.

Dorian is excited to tell Lord Henry of his new love, an actress named Sibyl Vane. She acts in a little theater that is in one of the poorer sections of London. Every night she performs a different role in a different play, but the role which won Dorian's heart was Juliet in Romeo and Juliet. He fell in love with her fair looks and her acting talent. He has been back to see her perform every night since he saw her as Juliet. He is enthralled with the young lady, who lives with her mother and he is convinced is quite innocent.

Lord Henry tries to tell Dorian that all actresses are alike, they are all dyed hair and painted faces. To Dorian, Sibyl can do no wrong, she is the total embodiment of what a woman should be. He feels he knows her well, because he has met her and seen her talent as an actress. Dorian no longer goes to visit Basil and has even stopped eating dinner with Lord Henry, due to his need to see Sibyl every night.

Dorian has convinced Lord Henry to come and see his beloved Sibyl perform. He asks Lord Henry to write to Basil, because he is afraid Basil is upset with him. He has not spoken to him in a long time, not even to thank him for the portrait.

Lord Henry sees that Dorian is not only in love with Sibyl, but he is also in love with new experiences. This love of new experiences is directly related to the effect Lord Henry is having on Dorian. He is exposing Dorian to new ways of looking at the world and this inspires Dorian to take it upon himself to go out and explore the world. Lord Henry is sure the passion Dorian feels for Sibyl will pass and he wonders how it will end.

Lord Henry goes out for the evening to dine and that evening, he sees in the sunset the colors of the new life bursting in Dorian. Upon his return he is surprised to find a telegram from Dorian for him. The telegram announces Dorian's engagement to Sibyl Vane.

Dorian has become totally under the influence of Lord Henry. He takes everything Lord Henry tells him to heart. It should, then not surprise Lord Henry when Dorian begins to explore London on his own. Lord Henry is surprised at Dorian's announcement of his love for an actress, named Sibyl Vane. Dorian is beginning to lead life a bit more on his own terms, which Lord Henry tries to temper so Dorian does not make any major mistakes. Unfortunately, Lord Henry is not quick enough to stop Dorian from becoming engaged to the actress.