Jack begins receiving rejections from several schools. Some of them he expected, but the one from Deerfield hurts the most, and he begins to believe he will be stuck in Chinook forever. A week or so after the letter from Deerfield, though, the school secretary summons Jack to the office to take a phone call—it is an alumnus of a school called the Hill School. The man, Mr. Howard, lives in Seattle and wants to talk to Jack in person; the school is “interested” in his application.
Jack is afraid that all of his escapist fantasies are about to come to a dead end. When he receives the call from Mr. Howard, though, his hopes for a chance at a great education—and escape from Chinook—are reignited in earnest.
Jack tells Mr. Howard to meet him at the Concrete drugstore—he knows that kids from school will be there, and he wants them to see him with Mr. Howard, who drives a Thunderbird. At the drug store, Howard and Jack sit in a booth and order milkshakes. Mr. Howard asks Jack about his education, and deduces that Jack is “bored” in Concrete. He assures the boy that he won’t be bored at Hill—but that it might be difficult for Jack in other ways. The academic work there is hard, and boarding school can be lonely, with social challenges of its own. He warns Jack that prep school is its own world, and is not the right world for everyone.
Jack wants to “perform” success and affluence for his classmates. Simply achieving a goal for his own personal gain is not enough—Jack wants everyone to know just how special he is, and to witness directly the realization of his most deep-seated fantasies.
None of Mr. Howard’s warnings, though, put Jack off the idea of prep school; he tells the man that both his father and brother went to prep school at Deerfield and Choate. They continue conversing—when Jerry Huff shows up at the drug store, however, and begins having lewd conversations with a friend one booth over, Jack gets nervous that Huff will expose him for who he is—an outlaw and a fraud. But as Mr. Howard and Jack pay the check and make their way out of the shop, Huff doesn’t say a word to either of them.
Jack is so desperate to use prep school as a vehicle for escape that he refuses to even entertain the idea that he wouldn’t be able to succeed there. As Jack juggles his different “personas” in public, he feels an anxiety tugging at him, and is relieved when the persona he is presenting to Mr. Howard remains unthreatened by Huff’s influence.
As Mr. Howard drops Jack back off at school, he offers him one more warning about the difficulties associated with going to prep school. He worries Jack that rushing into an environment he’s unprepared for could do more harm than good, but Jack insists he knows what he’s getting into. Mr. Howard bids Jack goodbye, leaving him with a business card and advising him not to worry. Jack watches wistfully as Mr. Howard’s Thunderbird pulls away from the school and speeds out of sight.
Despite all of his hopes for his own future, the end of his meeting with Mr. Howard leaves Jack keenly aware of the ways in which all his dreams and fantasies are still—for the moment, at least—decidedly out of reach.