I doing my first solo trip in Jan and I'm a bit nervous about eating out alone.
No reason to be nervous about eating, whether you're alone or with a group of 100 people.
What is it about eating alone that makes you nervous? Are you afraid of getting poor service because solo diners tips are not big enough to warrant the servers attention? This happens to me all the time, and it's a self-fullfilling prophesy - if the server figures he's going to get a lousy tip from me, so he doesn't try, well, I tip low because he wasn't trying. But it doesn't happen often at WDW; in fact, servers in many of the WDW restaurants will make an extra effort to connect with solo diners and make your meal more pleasant.
Or are you simply afraid that the entire restaurant will point at you and taunt "Look at the single person!" while laughing out loud? 'Cause after many years of dining solo in all sorts of restaurants, both at WDW and at home, I have never seen that happen, to me or anyone else.
Sure, a lot of people seem to think that any public activity requires a spouse and/or children, especially an entertainment activity like restaurant dining or seeing a movie. But it's not! Restaurants and movie and theme parks are for everybody! There's nothing strange about dining solo, even in the family vacation capital of the world - I do it all the time, and usually enjoy myself a lot.
You're simply looking at things from the wrong perspective. You're not "dining alone" - you're "going to 'Ohana!" Or Chef Mickeys, or Boma, or Liberty Tree Tavern, or whatever your favorites are.
You're not "going to Disney alone" - you're
Going to Disney World! Whether you have friends or family with you is nothing more than a trip detail, like what you're packing or what time your flight lands. The most important thing is where you are going and what you are doing, not who's with you when it happens.
And if anybody does point at you and laugh in a restaurant, just throw some food at them.