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There are many things in life that can be a risk even getting in a car each day is a risk. However, when you are living a gluten free life style due to a diagnosis, the risk is almost never worth it
Once of the things that can get those with any form of gluten sensitivity into trouble is taking risks with food. Most of this comes from going out to eat, although I am sure that more than once we have ended up with new recipes that didn't work out in our own kitchens. While a place may have items that do not contain gluten NGA (No gluten added), cross contamination is the biggest risk. If you are really good, have been gluten free for a while and know what you are doing, then the risk might be worth it. However, if you are still new or still healing then the risk can cause more harm than good. You need to give your body time to heal before you get into any gluten, even an accidental dose.
For example I have been gluten free for well over a year now, I am really good at knowing where I can eat, what I can eat and how I have to eat. My husband and I wanted to step outside of our normal situation. We wanted Thai food. We found a promising restaurant and walked in. In only one question we knew that we would not be able to eat at that location. I asked the hostess if they had a gluten free menu. Her reply is "I am sorry, what exactly is gluten?" The fact that the hostess didn't even know what gluten was meant that it would be unwise to eat at that location. While I missed out on what smelled like fantastic food. I also missed out on the pain of getting sick. In this case the risk was very much not worth the reward.
However, if you find a gluten savvy new place it may be worth it. As long as they know what they are doing. As long as you take precautions to know that you are safe then a little risk might be worth it. I know I have a trip coming up; I can't wait to try all the gluten free places in my hometown.
In the end the risk must be carefully weighed before it is known if it is worth the reward, if you are still healing then almost no risk is worth the damage to your health, at least when it comes to food. I cannot say in almost any other circumstance.