I also live in a small town....6,000. Yeah, we are pretty small. We have one restaurant that will take the time to answer my questions and often make sauces and other options safe for me, the other just doesn't care after all these years and they have other patrons attempting to order gluten free. The waitresses know more than the kitchen staff. Two weeks ago, I ordered some crab salad and I asked if the crab meat was real or imitation. She was told it was real......wrong! Imitation crab meat contains gluten.
Just try to order 'clean'. Steamed shrimp, shrimp cocktail or other seafood. For salads bring your own dressing and croutons. Sometimes a stuffed baked potato is good. Often times, I order a Wrap for lunch, unwrapped. Or a Chief Salad, with my own dressing. And if I have to pull some dressing or sauce from my purse, I don't find that any one minds.
I have found that most restaurant don't mind. They don't want to you be sick any more than you do. And for colleagues, just say you have food allergies and you are being creative. Smile it off. I can assure you, no one will be as concerned as you. And after a while, you can work with your local restaurants and with hopes, they can work for you too.