I'm still getting adjusted to the whole eating out while having all of these diet restrictions. I don't like being conspicuous, so I haven't really told anyone at restaurants yet. This is what I've done so far:
BEFORE YOU GO OUT:
1) google gluten free at whatever restaurant you are going to. I start with gluten free food and from there narrow down to what I can eat. Read nutrition facts, and google results from other people trying to eat like you. They will let you know their experiences.
2) know what you can get before going to the restaurant so you know you aren't stuck without anything to eat.
glutenfreemom.com has a lot more suggestions about going out, but they are a little hardcore for me right now.
So far, I have eaten at:
Abuelo's - They had a one page gluten free menu I had to ask for. I got the pork fajitas wrapped in lettuce, without the sour cream and cheese and with cilantro lime rice. It was absolutely delicious, and made me kind of sick. I think it's because it had black pepper on it and I didn't think about it.
BWW's - I looked up what I could have and came up with this list:
Traditional Chicken Wings
Naked Tenders with no seasoning
Pulled pork only
Ribs (pork) without glaze
--I was trying to play it safe and just ordered french fries and buffalo chips with the seasoning. Again, black pepper made me a little sick.
Jimmy John's - I had their lettuce wrap with turkey, cucumbers, tomatoes, lettuce, and alfalfa sprouts. It was quite delicious, and I didn't get sick at all! I asked the counter if the quacamole was gluten free, so they might have been extra careful...but most people give you a :/ face when you mention "gluten." It's like it's not even part of the English language.
Outback Steakhouse - Huge gluten free menu! Two pages :) They give little tips and stuff on what to avoid too. I got the Outback Special (steak) with lobster tails (no seasoning), aussie fries with no seasoning (it wasn't on the GF menu...i think i'll avoid these next time, it wasn't worth it), and 4 grilled shrimp. I ordered online and made sure to specify gluten/dairy/black pepper free in the special instructions. It comes with lots of sauces and ketchup, but I didn't use any of them, it wasn't safe to. Something got to my stomach but I'm not sure what....the steak was mediocre and had some fat lines in it, the shrimp had a strong seasoning but were pretty good, the lobster tails were delicious, and the fries were not very good.
UPDATE: Ate there again and this time specified NO BUTTER as well. Didn't get sick.
Things will be different for you if you live in the northern United States or in a more liberal place, from what I have noticed, since liberals tend to be more health conscious and have more gluten free options :) I live in South Texas, the land of fried things and gravy, so finding gluten free options is rather difficult for me.