Cookies really that bad?!

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Omit added fats / oils to keep your cookies healthier. Look up recipes at drmcdougall.com, pcrm.org, fatfreevegan.com. You'll be fine, just don't neglect to eat fresh fruits & veggies along with whole grains daily.

No. You wouldn't gain weight. The main problem is that they would be empty calories in the sense that they wouldn't give you the nourishment you need to have healthy skin, hair etc. It's also important for your mental well being that you eat well.
And if you're not getting the nourishment you need from what you eat, your body will crave more food. That's why a lot of diets where people eat processed low calorie foods that are full of sugar backfire.

That said, one or two biscuits a day is fine, just not the whole tray. And make sure that you eat them slowly and really taste them. Don't do anything else while you're eating them. Turn the radio off. Put your book away. Stop talking to people. If you're concentrating on what you're eating, you're less likely to eat more than you want just out of habit.

Honestly, I have a cookie every day. Organic peanut butter sandwich cookies. They're the shiz, and they haven't caused me any problems yet.

nope but you cant go over your calories in 1 day cuz then you will gain weight.

No...your body doesn't care if the calories you eat come from a cookie or a carrot to be frank, calories are calories....