I am not sure how "strict" you are having to be with the gluten free diet, but be aware that "flourless" does not mean gluten-free. Nor does "wheat-free" mean gluten free.  I stay away from barley, spelt, oats, oatmeal, beer, soy sauce, imitation crab meat (like in California Rolls) because all these items contain gluten.  Oatmeal and Chinese food were two things that always made me sick and now I know why!  This being said, some people find it sufficient to just give up flour/wheat products. My goal is to eventually figure out how much gluten I can have in my diet without a reaction.   Currently I eat about 99.9% gluten free.

If you are trying to be careful about any gluten intake, be cautious about eating out. I usually have no trouble at Mexican restaurants ( lots of corn and rice ) or at Japanese restaurants (the small amount of soy sauce does not seem to bother me here, or I just don't often use it ), or at Thai food, or at chain restaurants (lots of salad options, and I usually just use oil and vinegar on the side).  I mostly stay away from creamy dressing, or soups at a restaurant unless I feel like inquiring if they use flour as a thickener.   Italian used to be hard, but I have discovered I love risotto and polenta, and there is often a nice fish or meat entree on the menu.  The hot piping bread is tempting when I am starving, so ask for a tasty drink while others fill up on bread and enjoy your meal when it comes.  I also keep almonds with me, which are great at warding off hunger pangs!    As for desserts at nice places - ice cream, flourless chocolate cakes, and creme brulee are usually safe.