Your question about how to seek God more "accurately" on this is a great one to ask.Let me offer some thoughts that I hope will lend helpful perspective. Preparing for it can take a lot of time, but have you prepared for what happens afterwards as well?
Trust me, any female who doesn’t think you’re the right fit will refuse to loosen her boundaries. She will not insinuate any romantic Lady and the Tramp gestures. However, a woman is going to linger a little bit longer after saying goodbye if she wants some lip action.
If this is the case, she will definitely want to pay for her share to erase any guilt of rejection. With my experience in lackluster dates, I’ll quickly go in for the hug before any awkward “Should I kiss her? If she’s already checking Ok Cupid before you even step out of the establishment, you should start planning the next date…with someone else.
This ensures that no matter whether your date goes well or badly, you’re not leaving yourself exposed and open to self sabotage.
Debriefing It’s a good idea to arrange to call a friend after your date.
One thing to mention straight away is that you seem to be relying a lot on feelings to make this really significant decision ("unsettled," can't get "completely at peace," etc.).