Jackie Paper was a lonely youngster who played with his stuff toy, Puff the Magic Dragon. When he reached puberty, he became interested in girls and no longer played the imaginary seafaring game with Puff. This is the transition from the age of innocence, when boys and girls played hide and seek together and the boys played touch football and little league.At puberty, boys lose their playmates shift their interests to girls. Then one day, you have a crush on a girl and fantasize a courtship like Romeo and Juliet. All of a sudden, you forget about Puff who was tossed into the toy box along with the squirt gun, the bicycle helmet, plastic bat, and Robbie the Robot.

This song is about the idealism of youth that can achieve whatever they set their mind to before they get broken and indoctrinated by the system. The key lines are:. "We'd live the life we choose. We'd fight and never lose. For we were young and sure to have our way. " Over the years, as the youths age, they lose hope in achieving their dreams and thus lose their connection to the singer. This is explained in the lines. "Nothing seemed the way it used to be. In the glass I saw a strange reflection. Was that lonely woman really me" Be at last the singer is still a youth at heart along with her close tavern friends and unlike others in their age group, they haven't given up hope for fulfilling their dreams. Explained by the lines: "Oh my friend we're older but no wiser. For in our hearts the dreams are still the same".