I love makeup. I love wearing it, and I love not wearing it. ^-^
There were times in my past where I felt like I had to wear it, but I think I'm a little bit over that now. I don't think I'm (by pretty much any means) "confident" with myself or my looks, I just know that makeup doesn't change my looks so drastically as to put me into a whole new level of beauty. I'm me whether I'm wearing makeup or not. xP
I let myself have fun with it instead of stressing over how necessary it is or is not. I wear it when I feel like I want to, I don't when I really just don't care.
I think the most important thing is that girls and guys and everyone in between wears it for themselves. I know that view is done to death, but I mean it. There have been days when I've felt more judged for wearing makeup than I've felt for going barefaced, and I think being judged for EITHER of those is so very wrong. Have fun with wearing it, have fun with going completely natural. Whatever you do, do it for you, period. That's honestly my only view on it.