I honestly can't say anything about new dating as I am happily married. But what I think outfit/make-up all depends on the type of date. Lunch date requires a different outfit then a nice dinner date. You are lovely and he sees that in you so just be yourself. He was attracted to you, he asked you out so that is a positive sign I thing. You just be yourself on whatever date you two have. You'll be fine and he clearly doesn't need to go to the optometrist. You're a beautiful woman and he sees that so Woooooooooo you go girl getting dates!!!