I always eat by myself, since I usually go by myself...and I am one of those people who has NO problem going to a restaurant by myself....one caveat -- you need to make reservations just as if you were going with a group of 2 or 12...they don't set aside "single tables" and you can't get one without a reservation at peak times. Pick the restaurant you want, call Disney Dining and make your reservation, and go enjoy. I absolutely second the post above that says the timings get all messed up. Order your food, and ask for everything to be brought at the same time. I even order my dessert at the same time -- from experience, the last thing you want is to wait for 15 minutes for your dessert to be delivered while staring at the walls and wondering why it is taking so long. I ask for my check while I am dining as well, while one of the servers stops at the table to check how things are going. You can estimate 45 minutes for your entire dining experience. Note that the servers sometimes are MORE ANNOYING if you are sitting by yourself - some feel they need to come talk to you to keep your company, I guess. Apparently southern USA norms are different from northern USA norms where nobody cares if you are at a restaurant by yourself. I usually bring a book or magazine to read, or postcards to write, to avoid these unnecessary social intrusions. If they insist, I entertain them with tall tales -- "I train dogs for paramount pictures"..."I am a writer for 'My Name is Earl'"...
