First, the man should initiate asking the woman out.Whether this means approaching the woman herself or her father or someone filling that role instead of her father, it should be the guy that starts things off.
Every male who is out of college should have at least thought this through. Initiation is not manipulating the situation so that while you're officially "asking her out" there's no actual risk of rejection or embarrassment. It means that you as the man take the first step, risk and all. 'Doesn't that mean that she can just tell me no and leave me twisting in the wind? But whatever the circumstances, her role is as responder, not initiator.
Once he determines he is ready to be married generally, and once he has found a particular woman he is interested in pursuing, our single man's next step is to "put some feelers out." He should talk to some of her friends, see if she's been asking about him, have one or two subtly suggestive conversations with her to see if she gives anything away.... In his Boundless article, "Real Men Risk Rejection," Michael Lawrence eloquently summarizes both the objections some men might raise to this idea, and, in my view, the ideal response: 'Wait a minute. As single men need to learn how to lead (whether they like it or not), single women need to learn what it is to let a man assume spiritual leadership in the relationship — and to respond to that leadership.
But while you may be a boring dolt who is a complete drain on society, I’m a creative genius, and have perfected the art of openers.
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If you're still in school or not out on your own, disregard this for the moment. Your intentions and your feelings, to the extent that you can discern them and it is appropriate for you to share them, should be clear.
But if you're out of college and do not feel specifically called to singleness for biblical reasons, why are you not looking to be married? Albert Mohler has talked about a growing culture in society and in our churches of perpetual boyhood; some psychologists call it the "Peter Pan syndrome." As I said, in the Bible, marriage and family are considered a natural stage of progression toward manhood. Part of your role even at this early stage is to protect the woman of your interest from unnecessary risk and vulnerability by providing a safe context in which she can respond.
In my view, if you can't happily picture yourself married within a year, you're not in a position to date.
Third, once you decide that you are ready to date, look to God's Word to decide the kind of person to date, and evaluate potential dating partners on those criteria, rather than relying primarily on the world's treatment of ideas like "attraction" and "chemistry." I wrote at some length on this in my article, "Brother, You're Like a Six." For you busy singles with time for only one mildly irritating column per day, the summary is this: Pick a potential dating partner with an eye toward godly manhood and womanhood — with an eye toward who would make a good husband or wife, defined by those characteristics esteems in His Word, not the ones Hollywood likes.
Hollywood's perfect woman runs with the boys, knows what she wants and is aggressive en route to getting it — especially romantically. "What if I'm really interested in a man and he just isn't getting it and I need to move him along? When men drop the ball on leadership (as we often do), it presents a temptation for the woman involved to pick up the reins and lead for him. Picking up the reins sets a terrible pattern that only confuses the roles in the relationship and encourages both of you to take the role of the other to the detriment of the relationship and ultimately the marriage. If it doesn't work out with a particular guy because he didn't step up, the Lord will cause something else to work out.
Hilariously, Hollywood even writes these characters into period pieces, as if the normal woman at all levels of society in the 18th and 19th centuries was a post-feminist, post-sexual-revolution, "there-ain't-no-difference-between-me-and-you" libertine. Needless to say, that is not the biblical picture of the responder. Does this mean that a woman should never ask a man out on a first date? Does this mean that a woman shouldn't give the guy the assurance he needs by "leaking" news of her interest to him by way of his friends? He knows what is best for each of us, and all of us must learn to trust Him — especially about things that are really important to us.
All singles who profess Christ and aspire to marriage — even as a possibility — have this responsibility (even outside this area of life, we should all be trying to grow in Christ). If you're already sure of that basic answer, are you a growing and mature Christian?