I always ask. If you tell me you are vegan, I am going to come back and ask if you eat fish, eggs or dairy. (because I have had people with varying answers to that question). I may ask you to define "gluten free"--because I have had varying answers for that, too. ("I cant have anything with wheat in it" "I can't eat anything with wheat, rice or corn in it" "I can't eat anything with corn in it") I will then try my best to make sure that there is something you can eat on the menu!! Then, if you match, that goes in my master file, so I can make sure that you can eat at any future meals that I have a hand in arranging. It is important that you are comfortable, and not having to scramble for food. However, if you tell me that you have 14 different restrictions, then that may be difficult to pull off. There is a point where I would have to say, "I am sooo sorry, I just can't do it". And I don't mean allergies...I mean preferences. Allergies are always taken care of!