Hi...

Being little with a BMR of ~1300, it can be tough to keep the portions down... even with daily cardio exercise to increase my TDEE, even a 2,000 calorie diet will make my weight slowly increase over time.
I find it's a bit tough for me to eat a meal that's small enough to stay 500 under my TDEE w/ the 5-6 meals recommended sometimes. I try to aim for 3 meals per day but sometimes I have 2 or 4.
If I'm eating something like vegetables or lean meat that I prepared myself with little fat or calories, I don't bother with weighing it. I'll just estimate the amount of calories in it. But say I'm going to eat something like pasta, a bowl of cereal, or anything that can be more calorie-rich (and that I know too well it's all too easy to sit down and have 1,000+ calories in one sitting !!!) then I always weigh it with a kitchen scale so I make sure that I am getting just one serving of 200-300 calories, and round out the meal with more veggies. For me salad with low fat balsamic vinaigrette dressing is really a favorite way to allow myself to feel sated while having less calories, and that's one thing I never get tired of eating.
Anything that's pre-packaged, store bought or restaurant bought is always too big a portion for a short gal like me. I agree it can be very tough to handle the portion control aspect especially when you are trying to enjoy social life that involves eating at restaurants and so forth.
I suppose my biggest advice for someone who's having a hard time w/ portions would be to go ahead and get a kitchen scale to weigh things.
And of course it's best not to drink any calories, whether it be beer, soda, sweet tea or even juice... the only exception I make is fat free milk. I drink it several times a day.