Hah! I came here for this comment. My friends actually pick fun of me when I tell them I go to restaurants alone, but I thoroughly enjoy it. I'll usually bring in a notebook, a book, or something to do... and... take, my, time.
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 too. If you really want to throw people for a loop, bring a notebook to thoughtfully write in and snap pictures of your delicious food. I had no idea until after a few times doing this in Italy that everyone was assuming I was a travel writer / food critic. I literally had people at other tables ask me who I wrote for, and when I told them no one they didn't believe me and begged me to tell. It was awesome :)
I ate by myself at Gordon Ramsay's three-Michelin-Star restaurant in London, and got the 7 course tasting menu. It was awesome! I took photographs of everything and detailed notes. The maitre d' kept coming over to chat with me, and I was treated like royalty. I don't know if this is because they thought I was a food critic, or if they just treat everyone so well. It is a small restaurant.
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".
For me part of the awkwardness is purely physical. Talking doesn't require extensive use of your hands and the person you are talking to are generally at eye level. Whereas reading and writing feel much more like an interruption to the meal rather than a compliment to it.
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.