Re: First date set. Second guessimg myself a bit
You are thinking and obsessing about this waaaay too much. You barely know her. If she could read this, do you think she'd see confidence or fear?
Not being hard on you, A-D, we all went through the same for those of us who found ourselves on the market again. Be very wary of investing too much too soon or you WILL be disappointed. Enjoy the ride, be confident about your choices, and your dates will see this and respond in kind (if they like you)!
I know it's a learning process, and going to be lots of trial/error. The confidence will grow the more that you date.
My thoughts: set dates when you're both available (as long as she's free Friday, it's fine, better than Saturday for a first date IMO)
, go to coffee shops at first (less pressure, more casual that way), and leave alcohol out of it until a 3rd date. You need to meet women stone cold sober (both them and you).
"If you deliberately plan on being less than you are capable of being, then I warn you that you'll be unhappy for the rest of your life."
~ Abraham Maslow