As "Jeffty Is Five" unfolds, readers are ushered into the world of a narrator deeply immersed in the allure of yesteryears. This narrator is not merely captivated by nostalgia; he harbors a palpable discontent with the present day. Though he grudgingly acknowledges a few merits of modern life, he wistfully laments, "I still think we’ve lost a lot of good stuff."

This yearning for bygone days likely stems from the narrator's belief that his own childhood was unjustly taken from him. Twice dispatched from his home—first at five, then at ten—he provides scant details about these formative years, save for mentioning that his father's struggles and his own penchant for trouble were to blame.

Amid this backdrop of fleeting childhood, enters Jeffty, the narrator's cherished friend since both were but five. While the narrator, now revealed as Donald, has aged to twenty-two, Jeffty remains steadfastly five, untouched by time's passage.

To remain perpetually five might appear insignificant, yet Donald, now a man of business and responsibility, wistfully imagines the joys of eternal childhood—a realm where dreams still twinkle with possibility and magic lingers. In the glow of his own responsibilities, Donald mourns the innocence he feels has slipped through his fingers.

Despite his grown-up life, Donald relishes his outings with Jeffty. A part of him envies Jeffty's unchanging existence within a child's world. Yet, another part of Donald pities Jeffty, particularly because of his melancholic parents, whom he deems "awfully depressing." They are trapped in despair, lamenting their inability to witness Jeffty's maturation into adulthood, ensnared in what they see as a living nightmare.

Jeffty’s father, John Kinzer, is a diminutive man, shrouded in an aura of haunted isolation, unable to maintain a conversation or meet a gaze. Meanwhile, Jeffty’s mother, Leona, is gripped by a palpable fear of her son, believing that by keeping her home spotless, she might somehow atone for what she perceives as her sin: birthing this enigmatic child.