Your indentation is lacking in the main.rb. Your code should be indented on each of the when blocks inside your case statement.
You also repeat your menu of "crazy worded" choices before the while loop and at the end of each loop. You could just do the menu at the beginning of each loop and thus the menu would only be coded once ("DRY" Don't Repeat Yourself).  You could even put the menu in a method and call it from the top of the while loop. Just an idea.