Trying

Yes to food scales. No to sugary drinks, fast food, processed snack foods (potato chips, pudding, the salty stuff.) It's true that you can eat these things and stay under your calorie goal, but it will just make you hungry later, when you need to eat, but all your calories were used in unhealthy foods. And carbs like bread are important. Your brain and body need carbohydrates to function properly. Just avoid refined carbs, like bleached four, white bread, French fries. Lastly, avoid alcohol. That stuff stalls weight loss like nobody's business.
The trick to logging calories is knowing your portion size. The serving size is listed on the package, but it's really hard to tell what 3oz or 100 grams of something looks like. I got a food scale and realized I wasn't losing weight because I overestimated the portion size of my food. My diary reflected the package portion, but in reality, I was eating more calories than I actually logged.
Lastly, try to incorporate tons of fruits and vegetables into your diet. They fill you up without taking up calories. You can roast them, steam them, add them to pasta or oatmeal, make salads and smoothies with them; they are pretty delicious once you learn ways to prepare them that you like. You can do it! I'm glad you have a friend to try out this stuff with