Lately I have been asking DH where he plans on taking us, and then I look up the nutritionals online so I know exactly what I am going to order in advance. I don't even read the menu, I don't need the temptation. I order water with lemon to drink. I start with salad with dressing on the side. If I want something that is like 1200 calories, I give half of it to my kids, and save $ from not having to order kids' meals, so it ends up being like 600 calories. Yup I feed 3 people with 1 entree. Most restaurant portions are really huge anyway.
Otherwise places like subway, etc, have really good options for people watching their calories anyway. And every Mcdonald's has their nutrition info posted somewhere in the restaurant or you can ask for it at the counter and they'll give you the sheet of paper (it's on the back of the paper they lay on the trays)
You could also keep a list in your purse of common restaurants you go to and what you can order there and the calorie content of the items, so if someone is suddenly saying "hey let's go to olive garden" or something, you can go without feeling guilty because you already have a meal plan for when you go there.
The only place you run into problems is restaurants that don't have their nutritionals publicized, but even then if you have a good idea of the calorie content of basic foods you can keep your portions in check (like know how many calories are in a piece of grilled chicken, etc), and even ask if someone wants to split an entree, so at least then it wouldn't be as bad as if you ate the whole thing.
Don't be afraid of not cleaning your plate, either. There's no rule that says you have to clean your plate. If you feel full, stop. No shame in leaving leftovers (or taking them home for later).
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