The story goes like this, "Woman sees a man she likes. They express interest. She thinks he's too shy to ask her out, so she does the honors. They go out, a dating relationship begins, and everything is great. Woman starts to notice the man is not as initiative orientated as she would like him to be. She confronts him and asks him to be "the man in the relationship" and take the lead sometimes. He sees no need, because in his mind she is the one who asked him out first." Get the picture? Men are hunters, protectors, gatherers, problem solvers, and chasers to name a few. Women are nurturers, affectionate, talkers, emotional, domesticated, expressive, etc. Remember, no matter what year it is these are innate characteristics.
So for all you single again folks, just because you maybe reentering the dating zone, doesn't mean your skills are completely antiquated. Yes, there are some things that are different when it comes to dating in 2015, but when a man sees a woman that he wants to get to know, he will, I repeat, he will make her one of his priorities and figure out how to ask her out regardless if he's shy or not. Single ladies, please stop using the "he's too shy" line. Single men, although it would be nice to go all out your way to show her how much you want to ask her out, a simple, "Would you like to go out with me sometimes?" is still more than okay. Remember women like the little things--even the simple things when we know they are sincere.
Now if you are interested in a woman but still want to check her out without misleading her, a good way to do that is to take part in some group activities that you know she's a part of. Since going to church is something I hope you both would share, I'll use that as an example. Take part in a Bible study or small group classes that she maybe taking as a way to see how she thinks, and you can also use those study topics as a way to start a conversation.
Since you are single again, the one thing I would caution you to NOT do if you have the courage to be bold in getting her attention is do it exactly the same way you may have done it for your ex. Trust me that will be a big OUCH in the event this woman turns out to be someone special to you. Being bold and creative in your "asking out" approach is a good thing, but a woman ultimately needs to know she is unique.
I know, I know, I know it sounds easier than it seems, because who wants to be rejected? Trust me I really do understand, but I think the benefit outweighs the risk. I get tons of emails and questions about this very topic all the time, and my answer is always the same. At the end of the day, how else are you going to know if she will go out with you if you don't actively participate in the process? If she says no, then you never have to wonder, and you place her in your friend zone and move forward. I am cheering you on, and I know you can do this if you think she's worth the risk!!!!!