I go to parks with others and alone. Both ways are good.
With others, there is someone to talk to in line, which is very boring alone. Thee is someone to whom you can voice observations and who does that for you. It's more fun that way, usually. And you have a second person to help you remember things later. I found, when traveling, that I get a little lonely after a couple days. I do think cell phones with free long distance and texting are a big help there.
Alone, you get to do exactly what you want all the time. Don't like Peter Pan? Don't ride it.

Want to get up at the crack of dawn for rope drop? Nobody to slow you down. Feel like sleeping late, skipping DHS and going to the pool? Yay. You'll get much more down when alone in the parks, too. Even one other person slows you down!
I do not eat sit-down meals alone at WDW, especially character meals. I tried to do Crystal Palace once when I really felt like a sit-down, get-wated-on meal, but the characters think you want to talk to them, which I really do not, lol. If you DO like characters, they'll spend time with you. Piglet sat down at my table, lol. I will do sit-downs at CityWalk, though. Don't feel as weirded out there, not sure why.
I used to travel for work a lot and am not worried about going places by myself or self-conscious about it...but eating in the more busy Disney restaurants alone feels a little odd. Every table is full. And everyone is chatting. And the tables are all crammed in together, so you hear the people near you. It's loud. Disney is the first place I ate alone that made me feel at all odd about it.
I have no problem going to parks alone, though. But I do not stand in long lines. I'd be way too bored.
I don't know if any of that helped.
Good luck.