Hard to remember for sure - but I remember feeling a little awkward the first year or so that I traveled when i had to dine alone. I didn't let it stop me and now it's no big thing.
I think some of the awkwardness comes our experience growing up. You always think about going to the restaurant as a family or for a special occasion. It was always with at least one other person. As a teen, you meet up with your friends at a restaurant. So you just don't think of eating at a restaurant alone.