This Boy’s Life


Tobias Wolff

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This Boy’s Life: Chapter 29 Summary & Analysis

Jack meets Mr. Howard and his wife for lunch, and over the meal Mr. Howard happily reminisces about his years at Hill. At a certain point, Mr. Howard grows quiet and serious, and asks Jack if he has had any second thoughts about going off to Hill. He lets Jack know that there’s no shame in changing his mind, but Jack insists that he still wants to go to Hill—his mind is made up.
Mr. Howard seems both genuinely excited for Jack, and genuinely concerned about the boy’s ability to succeed at Hill. Jack, though, desperate to escape Chinook, does not entertain the idea that he could fail elsewhere—he just wants to get going.
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Mr. Howard and Mrs. Howard take Jack to Mr. Howard’s tailor, where he’s fitted for suits. Mr. Howard buys Jack an enormous pile of clothes—jackets, pants, suits, shirts, ties, sweaters, an overcoat, and several pairs of shoes. As Jack looks at himself in the mirror wearing one of his new suits, he sees himself as an “elegant stranger” wearing a “haunted expression.” Though Jack has no idea what the future holds, he feels cocky and hopeful as he imagines his new life at Hill.
Jack has spent the whole of his adolescence trying on different identities and personas, trying to find one that fits. Now, as a new idea of himself emerges, he excitedly greets the “elegant stranger” before him, unable to see how he will go on to struggle inside of this identity, too.
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