brooklyn19, you remind me of me 20+ years ago, and I think your self esteem is healthy and only hope that it continues! Just remember that there is a fine line between confidence and arrogance. I too wear makeup, not too much though. And I too look good!
As far as a lip gloss/stick for Pesach they often contain a corn starch derivitive, so it is not a kashrush issue but a kitnyos thing.