It depends where we're going for me. Eating out can be pretty expensive and so I tend to order the same wherever we go. I probably have about 3 or 4 dishes that I look for and as long as they serve one of them then I'm happy. While I don't mind trying new foods, I'd rather do that at home or when out shopping, then if you don't like a meal you've always got the other option to cook somthing else and you've not wasted a lot of money.
Well, my general motto is to only buy stuf at a restaurant that I could not easily replicate at home -- which will often be complex or expensive old avorites (anything with lamb is welcome!) or something new. For ice cream, I'm usually pretty much ordering the same stuff: at least two different flavours, one o them chocolate, the other one something "refreshing", most of the time fruits (often berries or any fun, fresh fruits. Not banana)
I used to order the same thing all the time. I've never been one to eat out a lot, so I didn't risk money often on trying new things. Also because I'm pretty picky and it's rare I like more than a couple items on the menu anyway. Especially these days.. I don't eat out at all anymore, though I'm finding more and more restaurants that cater to people like me, so I might be giving some a try. If I do, I'll be trying almost everything lol.