What do you do when you go to local diners?

I do two things. I use the database, looking for the most comparable thing I can find, usually picking something with the highest or near highest calories, so my guesstimate is a little padded.

Then I just don't worry about it.

This is a long term game of estimates. In the end, being a couple hundred calories off on one meal is not going to make or break my diet. The effect is negligible at best. I weigh my foods when I can, but when guests are over I generally treat it as a restaurant meal.

I find that the more anal I am, the less I want to count my calories. The more relaxed I am about it, the more sustainable it becomes. The fact is, I never even paid attention to calories before, and now I watch my calories every day. That's a huge change and the very nature of the change tells me I will succeed. So far, if I'm goofing up at all, it's that I'm losing weight a little too fast. I'll take that.