I wrote previously, and hopefully humorously, about some of the problems with our current conceptions in the church regarding dating. Essentially we've made it way way too complicated, resulting in way way too much pressure being put on an interaction which, to my mind, should be fun. Since I'm not one to criticize without providing a better alternative, here is an explanation of how I do it. I think it makes good common sense.
A typical first date (a movie and a unique dinner) will cost me $50 for both of us.
If It's worth $50 to me to get to know you better for an evening, I'll probably ask you on a date. Unless of course I'm concerned that you will misinterpret that gesture and it will lead to social awkwardness. Unless you are so repulsed by me that the prospect of spending the evening with me is not worth a free dinner, you should say yes.
A second date is usually much cheaper (maybe a picnic lunch and a walk) averaging maybe $20 for the evening. For this reason, if the first date went even alright, I'll probably invite you on a second. At this point in our interaction there is absolutely no commitment implied or intended. We may both be dating other people at the same time, that's fine, if not, that's fine too. If it doesn't go that well, I might even recommend that one of my friends take you out, that's okay, we're not getting married anytime soon at this point.
By the time I'm asking you on a third date It's safe to assume that I like you, I want to kiss you, I'd like to see this go farther. My idea of a third date could cost $100. I may still be interested in other people at this point and unsure about where I stand in your book, but if you got this far it's a safe bet that you are the most interesting girl in my life at the moment. If you are totally uninterested, you might consider at this juncture turning down the opportunity rather than letting me waste my time, But more than likely you are at least a little curious and it's worth it to me for a chance to impress you.
It might be, that for any of a number of reasons, our third date doesn't look like that and we just grab coffee or something. That means I'm not sure how I feel. It's a bad time to ask me. Either it will level out into a real third date and beyond, or it will slowly devolve into a friendship (or there will be some hysterical crying and throwing things at my car, but we're not going to go there)
After a while, if things are going well, it will get to the point where we are going on dates at a steady pace. This is called "going steady" or being in "a relationship". If you are seeing anyone else, now would be the time to stop (with one of us or the other). If you're not sure whether or not we're at that place, check facebook. It'll say "In a relationship" with you in my profile.
Simple enough?