> I've been under 260lbs for almost 2 years now and I still have to starve myself constantly to get back down to 220lbs even though I sleep well.

I weigh more than you but I've been successfully (if slowly, for most of the time) losing weight for several years, after having lots of the same kind of problems you describe before that. What seems to be working for me is:

1) Eat lots of non-starchy vegetables, especially toward the beginning of trying to establish a lower-calorie pattern. These can satisfy the need for stomach-fullness that develops over a history of overeating (over time, your stomach stretches, and it takes more volume of food to feel full), without the miserable feeling you get from eating too much caloric foods (I used to get different forms of misery from "too much carbs", "too much fat", and "too much protein" when I overate, but they were all misery.)

2) Eat more snacks between meals -- this helps level out your metabolism helps avoid the "starving -- must eat lots at next opportunity" feeling that leads to overeating misery.

3) Find one or more physical activities that you can enjoy for their own sake and do regularly. For me, it's been ballroom/latin/swing dancing, but the particular activity isn't all that important.

4) If you haven't already, try to get your doctor to check for metabolic conditions or vitamin deficiencies that might be making it hard for you to lose weight (I had a pretty significant Vitamin D deficiency and supplementing for that seems to have helped some, lots of other people I know have had bigger impacts when previously undiagnosed metabolic conditions were addressed.)

EDIT to add:

5) There's lots of approaches that are popular as to exact approaches to diet mix, and I've seen lots of people successful on different ones, but all of them -- including mine -- have included really sharply limiting sugar (often pretty much to whole fruit as the only sugar-heavy food, if even that.)

6) Drink plenty of water. For lots of people, hunger and thirst signals easily get crossed

I definitely am not eating enough vegetables and too much starch, which I know I have to change. Thanks for your other tips.

> I definitely am not eating enough vegetables and too much starch, which I know I have to change.

To reemphasize this, for some people, eating carbs will never fill them up! I am one of those people for sure, I'll eat cookies until I am physically ill, but I will never be satiated!

Think about this question: Which can you eat more of, twice baked potatoes stuffed with goodies, or just steak?

Next time you sit down for a meal, eat the 10oz sirloin first, before the potatoes. Then wait a few minutes and see how you feel!

Also make sure to avoid "healthy" foods that are anything but.

Bananas are a good example of this. Aside from some potassium, they are no more healthy for you than a candy bar! Granola bars are another great example of "healthy" food that leaves you feeling hungry! (I don't know about you, but I've never been "filled up" from granola bars! I know people who can be, but I am not one of them!) Finally, anything with the word "juice" in it should be avoided!

Finally, realize that your environment is one of the single largest factors in helping you achieve your health goals. Everyone says it is motivation, but hell, odds are you are plenty motivated. Feeling like crap and wanting not to is damned good motivation. But following through, ah, there is the hard part!

Environment matters. I got rid of all snack food from my house. All of it. Eating at home now involves zero willpower. My fridge has nothing but raw food that I need to cook. I have will power for all of the 5 minutes I am grocery shopping each day. If I am too lazy to cook my food, I go hungry, it is that simple. Each day on the way back from work I buy exactly the food I need to cook the meal for that day. (And yes, guests get used to this! "Sorry we have exactly the right amount of this awesome home made food!")

Change your diet. I don't mean "diet", I mean change what you eat forever.

What you're eating, in addition to how much you eat, is extremely important. If you eat crap (sugar cereal), you're going to feel like you're starving two hours later when your blood glucose levels spike.

Risking to be the 52768th guy to propose a fad diet: Have you tried going ketogenic (/r/keto)? I've lost 50 lbs within about six months without really trying. No hunger pains at all (the first week is hell on earth though).

Just avoiding carbs and vegetable oils and eating lots of (mostly saturated) fat made my weight drop. Don't count calories. Just start eating when you feel physically hungry (cravings don't count), stop eating when you aren't hungry anymore (not when you're completely stuffed).

Out of curiosity, do you eat diet foods low in fat? Do you eat a large percentage of packaged/processed meals or made from "scratch"? Margarine or butter?