Lost in the City features main characters from a wide range of ages, and one of the most interesting aspects of Jones’s collection is his organization of the stories by beginning with the youngest character and ending with the oldest. Three of the fourteen stories, or roughly 20% of the collection, feature children as the main character, and almost 25% of all the characters in the collection are children. Jones is allowing the traditionally marginalized or discredited groups of both the very young and very old to have a voice in Lost in the City. The stories portray a generational conflict through the young characters' indifference to older southern traditions.
In the story "Marie,” Marie Delaveaux Wilson's experience best exemplifies the gulf that is happening. The story juxtaposes the old values by showing the reality of life in D.C. with that which Marie records for George Carter. The new generation is no longer respectful of the old values which extends to disrespecting the elderly. Marie experiences in the stories leave her hurt and vulnerable. She resorts to violence as a form of asserting her presence in the city.
The family is crucial in instilling the young members with respectful manners. The city, however, altered the family dynamics which is translated in the behavior of the young generation. Two stories illustrate the young generation detachment for the older one. Caesar in "Young Lions" is kicked out of his father's house and gradually enters the world of crime. Elain Cunningham in "A New Man" abandons her family home and drift into the notorious life of the city. As a result, these two characters show no reverence to older people or traditions.
A notable generational rift exists in the stories. A young Black generation grows unattached to the old southern values and tradition of the older Black community. The gap is intensified by a gradual White encroachment that takes place through gentrification. Black citizens are forced to leave their own neighborhoods and relocate. Consequently, communal and familial ties are severed by a displacement which widens the gulf between the young generations and their attachment to their past.