i just got back last week from a 2 week solo motorcycle trip. New york to the grand canyon and back. Camped out every night with a bottle of whisky. Everyone thinks its so strange that I like to do that sort of thing but I am my best company. Nobody to slow me down, distract me, bother me.
It takes a lot of self confidence to be able to walk into a restaurant and order food alone. I do it all the time now, despite the fact that even a year ago I would never do anything alone.
I read a book about it and gave the system a try. First thing I did was go to a coffee shop alone, order a coffee and something light to eat, sit down, eat it real quick and leave.. Then I went to a bar alone and drank one beer and left. Then I went back to the coffee shop and drank the coffee sitting alone. Keep getting longer and longer, until you can actually eat a meal alone at a restaurant.
Now that I travel a lot for work, I can go to a bar in a strange city alone, and leave knowing half the people in there, and on occasion, a slut with no morals.