The story explains how the main character of the story, Charlie Hartz, committed suicide at the apparent height of his life. However, the title encourages readers not to think of Charlie for the way that he died, but for the daring and youthful nature with which he lived.

One of the lessons taken from the story is that appearances can be deceiving and that we never truly know what others are going through. Although Charlie was an involved community member, a friend to both the adolescents and the adults in his social circle—the leader of a successful business, and in a solid marriage—that does not signify he was healthy mentally. No matter how much a person possess materially or externally, it is not a reflection of their internal satisfaction, and sometimes people who suffer do not show it. This lesson promotes greater awareness of mental health versus prioritizing external, material things as the marker of a happy life. This can also be understood as promoting suicide awareness and suicide prevention measures in society. Suicide is a traditionally stigmatized topic, but it is a mental health epidemic that everyone should become more educated on.

Another lesson has to do with how the narrator, Martha, was drawn to Charlie. As reflected in the title, he was the man who jumped off the diving board with young people. His love for swimming is a metaphor for his love of living life fully and deeply. This is the part of Charlie that Martha admires. He had a positive effect on her life even though he was of a different generation; his ability to connect to people of all types, and not be afraid to "dive" into encounters or new experiences, reflects his open-mindedness and kindness. The lesson is to appreciate those we love and to not take for granted the importance of kindness.

The only hint of a suicide note left by Charlie Hartz is that he kills himself on Paradise Lane. Jeremy is convinced that this is "corny" and an "existential gesture." The narrator's father tells her that Paradise Lane is meaningless.

Charlie has a wife, a child, and lives in an extravagant house with a huge swimming pool. He is a successful businessman. He has friends and is always interested in being productive. He enjoys diving and is "very determined about it." He is forthright when talking the narrator and younger people and they respect him for it. Charlie even provides opportunities for the narrator and Jeremy to be together. The narrator also says that Charlie was interested in the lives of her sister, Jeremy, and herself: 

What kept people like me and Jeremy and my sister around him was that Charlie got the best out of what you were at the time you were it. 

Other than the narrator's comment that Charlie rarely laughed, there are no real indications that Charlie is depressed or upset. No one really knows why Charlie killed himself and this is the point. Charlie seemed to be a stable, relatively happy person. He was always involved with some project with a number of people in his life. He took an avid interest in other people and encouraged them to better themselves. Perhaps one of the points the author is trying to make is that every person has a story. Every person has their own battles to fight and their own emotional and mental problems to face. Some, such as Charlie, do this internally. Evidently, no one had gotten to know Charlie the way he had gotten to know everyone else. As much as he reached out to others, someone should have reached out to him.