Well, first off, it takes time. Over time, you'll not only internalize rough calorie counts for specific foods or food groups, but you'll also be better at eyeballing portions. So, for example, you'd know that broccoli is about 25 cals a cup, and you have about half a cup on your plate, so you've got about 13 calories of broccoli. Or, if you had 2 cups of spinach, you'd know that was about 14 calories total. You'll learn these values over time for the foods you eat often, and can make educated guesses about similar foods - When in a situation like that, I know that green, non-sweet veggies (like cucumber, broccoli, etc) are generally around 25 calories a cup or less, lettuces are under 10 calories a cup, starchy veggies like corn and peas are around 100 a cup, etc. This allows me to keep an eye on the calorie count so I'm not blown away when I track at home later.
Second, when its really impossible to know, I try to keep amounts moderate for non fruit/veggie items - for example, with the poppyseed dressing, I would have done as you did and had just a little bit, then put it into a calorie counting program like FitDay when I got home. Its not exact, but it gives you a rough estimate.
Combining these two strategies should help you reduce some of the anxiety around not knowing calorie counts on all foods when you eat out.
Hope that helps!
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. I'm getting better at eyeballing portion sizes though. I do measure things at home though... my DH is constantly complaining about all the dirty measuring cups and spoons LOL.
