I don't worry as much about calories as much as I do about portions - the way I see it, get a light appetizer (something that can possibly be shared between 2), then a satisfyingly filling main course, and a glass of water. If there is room for dessert, then make it a point to share it (provided it's a gracious amount). Then, go for a walk after to help with the digestion.
YES! I dont usually worry too much about calories, but it is so difficult to find healthy options when eating out. Often restaurants take relatively healthy foods, like say a vegetable stirfry and make it unhealthy by using an excessive amount of oil to cook it. It is also so frustrating that healthy options such as salads tend to be the most expensive thing on the menu.
I've spent a lot of time travelling, which means eating out constantly and this made it very difficult to maintain a healthy diet. In some countries, such as Serbia, most restaurants only serve junk-food style meals so it is very hard to eat healthy without your own kitchen!