I'm on my own schedule when I eat alone. I can eat as slow as I want to, I can order as fast as I want and what I want, I don't have to think of things to talk about, etc. I absolutely love people watching as well, so when I want to take a break from my food or my work, I can sit back and look around the room and check people out.
I'm that guy. I love it.
More recently I ate at Frank Pepe in New Haven and a couple at another table invited me to eat with them. How often does that happen in the US? Maybe all the time if you eat alone! But I felt like I was in Europe.
They kept wanting to know if I was a food critic. They seemed a bit skeptical that I just love good food. The fact that I have a nice camera might make me look more "professional".
That is what they are there for. Just don't go in there looking homeless and you'll be well received.
Then I realized that other diners, strangers, have no way of knowing whether or not I'm out on business or in my own city. After that, I got a lot more comfortable eating alone wherever I am: for all these people know, I could be a travelling businessman or have any of a dozen other "legitimate" reasons to eat alone.
Of course, in actuality, no one there even cares or notices me. But I found having the right mental frame helped it not bother me.
I've also found I get pretty awesome service when I eat by myself, and I get to focus on the food more which is nice. It's peaceful.
The one little break I have during lunch I don't want to be talking about work. I want to enjoy where I'm eating or more often than not I go eat my lunch at the beach or a park in between clients and might listen to music or a podcast.
When I do go to restaurants alone even if it's a nice place I will sit at the bar. I like to make small talk with those people if it is not busy.
Along with eating I go surf, golf, and skate alone a lot of times. However, with all these things I generally end up meeting and talking with people. Sometimes I don't though and it's nice just to focus on the activity and just enjoy that.
It's nice when people will come eat, surf, golf, etc. with me. However, given time constraints I don't let people not coming with me a lot of times get in between me going and enjoying a place or activity if it's something I want to do and that's the time in my schedule that permits me the time to go do that thing.
My hypothesis as to why it feels awkward is that one is afraid that other people might think, "Oh, look at this guy, he can't find anyone to go out to eat with him". But this is stupid, because obviously those other people that are there in groups don't go out every night to dine with friends either. They might just do the eating alone nights at home by themselves. Which objectively speaking seems no much "worse" than doing it in a restaurant, except that it is more hidden from the public.
So, just realize that those other people also eat alone, but when they do they might be too scared to even go out and rather sit at home. That makes you brave and adventurous compared to them! ;-)
The thing is that I've never felt comfortable when eating out with acquainteces, for one thing because I'm very slow eater so I'd always left lots of food on my table, and second because I've never been at ease with talking when your mouth is full with food. Plus you cannot made dirty jokes when someone's eating :)
As things are like I know, myself eating alone and at ease,I've discovered that I really do enjoy good food and a nice drink (I was almost indifferent to it before) and that I'm not that keen on making compromises anymore when it comes to eating out, because the decision where and when to eat depends only on me. And I've also become a lot more confident when talking to complete strangers, this coming from an introvert guy.
And on top of that, people watching and listening is extraordinary!
If you don't want to sit at a table, typically restaurants have a bar area where you can order food and it's not as strange to see people dining solo there. It's also socially acceptable to chat with other people at the bar.
I guess it's because food is powerfully social. Whether its the idea of breading bread with a stranger when you're travelling, or eating dinner with your family, or taking your other half to a nice restaurant, there's very strong social imperative when it comes to eating - and it's one which exists in pretty much every culture that I can think of.
It's pretty normal for me now. The only restaurants I won't go to are the ones that are very fancy or where there is a huge social aspect to it (e.g., Korean BBQ restaurants; I've heard they actually turn singletons down! I don't want to risk that.).
You might be joking, but don't worry about "scoffs" from people you don't know and will never meet again... you can learn things from them and move on.
However, I am not a spontaneous person. I like to plan things out a lot. Especially because I live in a huge city where I must drive (and I hate driving) and things are so far apart from each other. I guess this could motivate me to be more flexible, think on my toes, and generally improve what some may see as a character flaw.
Maybe one day.