Do you have some set calorie limits for each meal and snack and for non-water beverages? For example: 100 cals per snack, 300 per lunch/breakfast, 500 per dinner, 200 for non-water beverages, or something like that? (numbers would vary, depending on your daily calorie limit) Having a framework helps simplify calorie counting for me, so I'm not weighing food or keeping a notebook every day.
I also break each meal down, too...not so much breakfast or snacks, but lunch and dinner, might be 100 cals for veggies, 250 for meat, which on the above plan would leave room for a sauce, dessert, or other side dish...see what I mean? When I shop, then I just buy in bulk and pre-portion food when I store it. For example, I buy half a salmon, and cut it up, weigh it, season it, and put it in individual freezer bags, so that one portion of salmon equals one portion of chicken breast equals one portion of steak or whatever other "meat" I might buy. Same for veggies, I can just bag them up so each baggie holds 100 cals worth of whatever it is. Meal planning is as simple as picking a veggie, picking a meat, then picking a side or sauce or dessert. This keeps the day-to-day stuff easy, and eliminates the need to write everything down every time I eat.
For eating out, I just have a few rules: I don't do it often, maybe 2 times a month. When I do eat out, I make sure it's worth it: I'm not going off plan for a trip to Taco Bell, you know? I'm going off-plan for something special, and yes, I'm having the dessert! On these occasions, I don't count calories at all. If I'm working toward a specific weight goal, I'd rather put off the special dinner than have to count my calories and obsess about it, when it should just be a good time, not all about the food.
If you did want to count those cals, then having set guidelines for each meal can make it easier. Say, you skip one snack that day, make the other half the size it was, and skim 100 cals off lunch...save all those for dinner, then you've plenty of cals to eat out, enjoy yourself, and still come in close to your goal for that day. If you go over, you can always skim a little off the next day to make up for it, if it's bugging you.
When I get stuck with "obligatory socializing" that will involve food I do not want to eat, I just make sure I eat at home before I leave, or at the least, scarf down a protein shake, which will carry me through several hours of watching other people eat.

Hope that helps! (and WTG on your weight loss so far!)