I have an uncle, & some other relatives who have been associated with flying, but my personal favorite story is about a man who wanted to become an aviator, but never managed to achieve that goal.
My great-grandfather, Irvin John Koehnline, had a lifelong fascination with aviation. He had wanted to study flying & get a pilot's license, but was enlisted into the Army (1st Lt., 324th Field Artillery) for WWI before he could chase after that goal. At the close of the war, he entered into a program allowing American soldiers in France to study at the University of Paris, where he studied aerodynamics, in the hopes it might help him become a pilot.
Matriculation of I.J. Koehnline at the Univeristy of Paris, ca. 1919
However, when he returned home, I.J. never managed to realize his goal; he worked for a couple years as a lab assistant to a research metallurgist in Wheeling, WV, until the scientist died, I.J. got married & he took a job as a steel salesman for the Wheeling Steel Company. However, though he gave up on what had once been his dream, he still hoped he might be able to impart his love of flying on to his son, which is why, when my grandfather was less than two years old, I.J. had him taken up in an open-cockpit plane, which he believed & hoped might inspire his infant son with that love of flying. As you might expect, it had the opposite of the intended effect. My aunt still has the ticket stubs from the flight in a box somewhere, but she recently moved & I didn't want to burden her with asking if they could be scanned for me. I will get that done when I have the chance, though.