Not sure if any of you have heard of Precision Nutrition, but I think they have a great way of dealing with portions. I’ve gone through their coaching course twice now, and have really enjoyed it.
They don’t promote calorie counting, but using your hands instead. As an initial guide for men, at every meal try to get 2 fists of veg, 2 palms protein, 1 cupped hand of carbs, and 1 thumb of fat. Further details (and portions for women) can be found at Forget calorie counting: Try this calorie control guide for men and women - Precision Nutrition. Really helpful when eating out to get a rough idea of what you need to eat.
They also had a “rule” of 80% which really helps to cover for life situations. Say you eat 4 meals a day - thats 28 meals a week. The 80% rule means that 5-6 meals during the week don’t have to be perfect. In the grand scheme of things, 80% compliance is pretty good. Take into consideration date nights, food with friends, food with family, etc. Whilst it may not be your ideal, you can pick the best option and still be totally happy. This allows you to not stress so much, and enjoy the moment.
They’re also a big fan of experimentation. So you can start with that portion guide for a few weeks, and adjust accordingly.