Notify the Restaurant Beforehand.
Think back to when you were in school (for some of us, that’s a harder challenge than others): Did you prefer when the teacher popped a quiz, or when you had advanced warning to review materials and make sure everything was in order? When dealing with the gluten free diet, most restaurants are going to prefer the latter.
When you can, it’s best to make reservations and let the restaurant know about your special dietary needs in advance. This gives the restaurant time to get up to snuff on the details of the diet, look into what might be gluten free for you, and (sometimes) even make special accommodations.
One of the best gluten free experiences I had in Philadelphia was at a restaurant called Lolita. They didn’t have a gluten free menu, but were recommended as well-versed in the diet. When we visited (after calling a few days in advance), the kitchen had gone through the menu and marked everything on it that was gluten-free for me (about 90% of the menu, btw). It felt great to have so many options to choose from, but it was even better that the whole exchange was seamless and hassle-free.