Most of the second half of the book takes place around the Honeychurch residence at Windy Corner, on Summer Street in a small country town in the Surrey hills of England. It is a wealthy town filled with members of the leisure class. Lucy has been home from Italy for a week. A young man named Cecil Vyse, of the Vyse family whom Charlotte and Lucy visited in Rome, visits, and, for the third time, asks Lucy to marry him. Lucy's mother, Mrs. Honeychurch, and her brother, Freddy, observe this process from the drawing room. Mrs. Honeychurch approves of the match, judging Cecil to be bright, rich, genteel, and well-connected, but Freddy has reservations that he can't fully explain.
Cecil enters the room with the news that Lucy has accepted his proposal. Everyone expresses their happiness, and Cecil suggests that Lucy take mother and brother out to the garden to tell them about it, while he writes to his mother. Alone, Cecil reflects upon how he came to know Lucy in Rome and admired her for her reticence, picturing her like a painting by Leonardo, whom he loved "for the things that she will not tell us," things "not of this life." He proposed twice in Italy, and though she gently refused him, they remained on good terms. He asked permission from both Mrs. Honeychurch and Freddy on the most recent attempt as he wanted support, and Freddy was somewhat rude in his response.
Mr. Beebe, now rector of Summer Street, arrives to have tea with the Honeychurches. He brings news that two villas, named Cissie and Albert, have been bought by Sir Harry Otway from a Mr. Flack. Without mentioning the engagement, Cecil discusses Lucy with Mr. Beebe, who compares Lucy to a kite waiting to find its wings and fly away. Cecil suggests that the cord has finally been cut, and announces their engagement, then inwardly regrets, too late, the arrogance suggested by the metaphor. Mr. Beebe is taken aback but manages to wish the couple well.
A few days later, Cecil and Lucy attend a garden party at which Cecil finds the local population highly provincial. The topic of Mr. Beebe comes up, and Lucy remembers the chaplain in Florence, Mr. Eager, who accused Mr. Emerson of "practically" murdering his wife; however, she changes the name to Harris to protect the Emersons. In her vehement expression of hatred for Mr. Eager, Lucy surprises Cecil, who finds her ranting to be unwomanly.
The carriage drives past the two ugly little cottages, Cissie and Albert, where they find Sir Harry Otway, who regrets that he can't take them down because Mrs. Flack, a sick old woman, still inhabits Albert. He must therefore find a suitable tenant for Cissie, someone who isn't the "wrong" sort of person. Lucy suggests the spinster Miss Alans, whom she met in Florence, and proposes to write to them, as they need a home. Mrs. Honeychurch, however, suggests finding younger male tenants--people who are going up rather than down in the world.
Cecil and Lucy walk the rest of the way home, and Cecil expresses his disapproval of Sir Harry, whom he regards as brainless. Lucy asks him whether it matters so much, and Cecil says that it matters very much. Cecil wants to walk in the woods, asking if Lucy would feel more comfortable there than in a room, and Lucy assents that she would, more than in a room with no view. At a clearing, Cecil asks if he can kiss her, and she agrees, but he realizes too late that he has asked awkwardly and should have simply kissed her.