hey lets not be so hard on the guy, he just needs to see a doctor..lets see if I can help.
hmmm...
-just retired from his career early, tying to conquer new challenges

-lost his lady to an assistant (explains why he doesnt want to be a co pilot or assistant to anyone)

-the need to buy expensive items to make himself feel better. expensive watch, citation jet, a red sports car too??

-imaginary little black book

hmmm sounds like you sir have a case of.. midlife crisis. It's ok Ed.. this is common in men of your age who have some insecurities about themselves. Aviation is not the solution Ed. Becoming an airline captain of a big..long...powerfull jet wont make up for your apparent shortcomings. You know there are alternate methods to fixing that little problem of yours.

Do you concur doctor?