Anonymous wrote:OP here. I did forget to mention that I have a ton of face acne that I am still working on through dietary & topical medicine changes.
If you have not already tried it, may I highly, highly recommend Tretinoin. I waited until my late thirties to try it because I finally felt just too old for acne, and I could tell a difference in the first week! After 2 months, no acne and hyperpigmentation is fading. I ended up going through Apostrophe which is an online distributer, took a 20 minute quiz, and got it a few days later. One of the most productive 20 minutes of my life!
I recommend a good haircut that is flattering but not high maintenance, and as a PP mentioned, smiling a lot makes anyone attractive. A little blush and lipgloss perhaps some mascara is what the majority of women wear as makeup for a first date, but if you don't want to, the haircut will be plenty.