I'm going to say no to this just because I'm worried it will add an unneeded level of complexity, because first we'll have to gather volunteers to be dates, and then actually pick winners (which I wanted to avoid doing), and then make sure they get their "date."

I understand the desire to get more CR going but I think we'd benefit more from making sure there's lots to do in the mingle log itself than try to set up dates as prizes. I also think if there's going to be prizes at all they should be small things that can be given out based on general participation (candy, sweets, stickers, etc) - it's a little "everybody gets a gold star" but it's a lot easier to set up OOCly and I feel like fits in with the spirit of the event more than setting up dates or slaves for specific winners.