It does get easier over time, but I don't think I will ever get over the jitters whenever I eat out (unless it is a trusted restaurant) or when I eat at a friends. The first time I ate at a friends, was a lady who loved to cook and who knew I was gluten free. To make it easier for her, I brought my ingredients for her to use. For whatever reason, she did not want to use my ingredients, she bought her own. They were gluten free, but they also had flax in them, and flax makes me just as sick as gluten. Needless to say, her food did not go over well with me. Now I've learned to eat a bit before going to a friend's house, then I can say "I'm not very hungry."
Another time, I was going to travel. I did my research and picked restaurants that advertised they were gluten free or had a gluten free menu on their websites. However, when I arrived I found out that one of the restaurants was not really gluten free. Needless to say I was mad and they lost my business. My most trusted restaurants are any Mexican restaurant (and the South is full of them), plus Jasons Deli and certain foods at Chick-fil-a. They are my trusted ones that I've never had problems with.