Youth and camaraderie pervade this series of short stories in About a Boy, Stories, pertaining to an unlikely band of fledglings called Pineapple, Shoehorn, and Cantaloupe. Their nicknames apply to their hairstyles: the parted hair of Pineapple, the mohawk of Shoehorn, and a shave on Cantaloupe. They meet with Frock, a girl with a fashion statement, and Stroodle, an old wanderer. Big Teeth is their pandering adversary. Their school week is anything bandying another Saturday, and Pineapple as leader must decide amidst uncertainty whether he is a go-getter or the begotten heel.

The story delves into their daily challenges-from interpersonal conflicts to existential musings-framed within everyday settings that spur deep discussions about future aspirations and their paths to achieving them.

The collection consists of five stories, each told from the viewpoint of a different character. One of the stories is told from the viewpoint of a female character named Frock; this adds an interesting twist. The characters in the stories are identified by their unique names, as well as their individual voices, which are intended to reflect their different personalities.