(Thank you for the kind words. I know God is using me and it is all Him, not me because I mess things up. I'll share lessons from Hawaii to prove my point that I am VERY much a work in progress)
After about 18 mos of accountability every Sat at 6 a.m. (separates the sheep from the goats) with a group of brothers, I have learned how challenging these issues are for singles, both males and female. from some of my missions trips, I know many of the single sisters also desire to honor God yet not miss out on the "one" God has for them. As I read your post, I know the concern you have is shared by so many of the singles in my church. No one wants to miss out, be overly cautious etc.
I believe God will let us know in no unmistakeable terms when someone is Not "the one" and I have to trust that He will bring the our mate to our attention even if we aren't really thinking about them in that kind of way. This is why I explored both potential relationships and was at peace when each wound up NOT being the woman God has for me. My experience in witnessing my other friend find his wife while serving together in Romania also shows me that God will work things out ways we might never imagine. He prayed about going and stepped out in faith even though he needed money and his employer's favor in order to go. The end result was God working on both his and her hearts while serving in Romania and now they are married.
You mentioned "playdates" and the only thing I could suggest is getting together within groups to see some interaction in such a setting and also to be accountable. Amongst the singles in my church, there have been group social functions some have participated in and we have mixed in serving the congregation at other functions. Beyond that, some one on one time in public places, coffee dates seem to be the favored way to get to know the other person once there seems to be some mutual curiousity.
It will work out The Lord knows the desires of our heart and it gives Him pleasure to fulfill those desires when they are aligned with His will. If He eventually chooses not to meet those desires, I tend to believe the desires will change along the way so that in not meeting those desires, we are not disappointed when we realize our desires have changed.
Some may see my reasoning or logic as circular but I could probably find significant biblical support if I meditated on it.
Long ago, I wrote that I wanted to be so busy about my Father's business that when I wasn't thinking about "Ms. Right" she appeared without me really thinking about it. I still think the more I focus on Him, the sooner I will be ready for what He has for me.
Right now I am busy serving my Lord in any way I can and I trust He'll meet my needs and maybe this desire to one day be equally yoked.
Committed2Him- "C2H" All Things (Back from Spain!)...18