Scared to up my calories

It's not stupid for you to ask. In all honesty, I would say that you do know what is healthy. You know that fruit is and ice-cream isn't.

But I would say that you should:

Eat AT LEAST 5 portions of fruit and veg a day (1 portion= a handful/ usually around 80g) Aim for 7, and veg are better than fruit really, although I never manage 7, and eat more fruit anyways, so it doesn't matter too much.
Eat breakfast every day.
Have a snack, whenever you get hungry, make sure you have healthy ones with you, I always have an apple on me, but any fruit, veg, veg and dips (eg carrot and hummus etc), nuts and seeds are good, but can be high in fat, so don't eat too many.
Then lunch, and I would recommend another snack later then. Then dinner.
The purpose of the snacks is to try to keep your blood sugar reasonably constant, so you don't get cravings or feel suddenly really hungry, so that's also important.
Drink quite a lot of water. Try to drink 2litres a day, and try to drink at least one of those as WATER, not coffee or tea or squash or whatever. And don't drink your calories, like having full fat soda, or even fruit juice all adds up. The easiest way to drink water is to make sure you always have some with you. Often when you think you are hungry, you can just be thirsty, so have something to drink, then wait 10 minutes, and you might not be hungry anymore.
You can weigh your food, when measuring it, cups and stuff can be used, but is less accurate because of heaped cups and level ones or whatever, but weight is more constant, the trust the content on here is usually really good.
Count what you eat, by putting it into myfitnesspal, and make yourself accountable, it's your responsibility. Try to be aware of everything you eat, but don't be obsessed by it, don't think one cookie is going to make you gain a pound, it won't!
Make sure you notice what you're eating, and try to pay attention to the way it tastes, the texture, smell etc, really appreciate it and take your time. And try to stop eating when you're not hungry anymore. You are always allowed to eat later if you get hungry again. If you are hungry, then feed yourself, you are allowed!

I try to ignore fad diets, a fad diet is usually a bad diet, so don't even try. You need all food groups, and a balanced diet to be healthy.

Cardio will burn more calories, but weight training will make you look better, and make you burn more calories every day. Therefore I would do both. Try to focus on diet, and try to up your cardio, but it is difficult to say how much is the right amount. Remember that 10 minutes is better than nothing.

Don't expect to lose more than 1.5bs a week, even that is really great. It will take a long time. I normally lose 2lbs a month, but I am losing weight consistently, and it all adds up. Don't get cross if you gain, and try not to weigh yourself everyday, or get obsessed. A lot of things can change your weight. I would also say you should take photos, every 4lbs lost or so, and take measurements.

I really hope this has helped, and if you want to know anything more specific or ask anything, you can send me a message, or probably reply here, not sure how this works....

Good luck!!

Xxxx

I also recommend one of the books by my personal favorite fitness superstar, Jillian Michaels. "Master your metabolism". I'm reading it again for the 2nd time right now. She has a lot of practical, common sense advice, and a diet / exercise plan all spelled out for you. Her theory is that you can eat healthy, DON'T starve yourself, and exercise a reasonable amount, to maintain a healthy weight and lifestyle. I have done it and it works, but I had a bad year last year and have to start all over again!