How to become pretty?

You're already doing a lot of good things that are going to make you "feel" prettier and therefore be more confidant. Even ugly ladies and get good looking guys if they can work it and have confidence. Don't go over the top and worry about your hair like crazy as long as it isn't dirty or a rats nest guys don't really care that much. As far as the dark circles go. GET MORE SLEEP, that is the number one answer there. Either that or apply a light layer of foundation or cover stick over the dark circles to match the rest of your skin tone. Try not to overdo it with the hair and makeup if this guy already knows you because you will make him think you have become high maintenance or have gone crazy since you last saw each other. As far as moisturizer goes if you have dry skin, Olay makes wonderful products and you should always work on keeping your skin moisturized anyway because it makes your skin look healthier. Last but not least, ask him out, ask him if he wants to hang out, chill with him as if you would with any of your friends, If you act shy around him someone else is going to nab him, that and good luck!