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How to keep homemade cookies soft
Add some extra butter to the recipe.
Consider your sugar to butter amount carefully. If you have more sugar than butter, you will usually have a harder, flatter cookie, but if you have a little extra butter, you will have a softer, more chewy cookie.
Even though it's a little more calories to add to your system, they will stay much softer. If you are worried about calories and whatnot, get unsalted butter or put in a little more oil instead.