Christian Singles & Dating

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He Said-She Said: Dating a Separated Man, Women as Initiators and More

  • Cliff Young & Laura MacCorkle Contributing Writer & Senior Editor
  • Updated Oct 19, 2010
He Said-She Said:  Dating a Separated Man, Women as Initiators and More
EDITOR'S NOTE:  Each He Said-She Said column features a question from a reader with responses from a male and female point of view.  If you've got a question about anything related to singleness, please click here to submit (selected questions will be posted anonymously).

It's "grab bag time" once again, and we've decided to answer more than one question in this edition of "He Said-She Said."  We receive so many questions that there are simply more questions than there are months in the year!  So we've selected six that don't warrant lengthy answers (or rather, ones we felt we could answer well enough with fewer words) and have combined them into one column.  We hope you find them helpful and encouraging.  Enjoy!

QUESTION:  Someone I worked for 27 years ago, who was married at the time and with whom I had only a working relationship, popped up in my life last year.  He and his wife are separated and have decided to get divorced, but the division of assets is an issue.  My question:  Can I, as a Christian, date someone who is separated, with the divorce proceedings in progress but still not through? 

HE SAID:  Can you?  Yes.  Should you?  No.  It doesn't matter how far along the divorce proceedings are, how "coincidental" the reunion was, or how much you enjoy one another's company, the man is still legally married.  Carrying on a dating relationship with a married man is emotional adultery. 

You don't know God's plan for his relationship with his wife, but if he brought you and your former boss together, the (future) relationship will survive the time it will take to divide his assets.  By dating now, you will be moving ahead of God's plan and will for your life.

SHE SAID:  Well, my answer is pretty simple:  Is the person not married?  No.  Is he still married (even though he is separated) and still someone's husband?  Yes.  Therefore, you would be dating a married man.  The end.

QUESTION:  How can one encourage a Christian sister who has trusted God for a life partner for 23 years and is still single?

HE SAID:  Continue to encourage her through your words, love, and actions.  Include her in your activities, but try not to center on the family or relationship she doesn't have, but rather emphasize those areas where God is allowing her to do things you aren't able to and how she is being used to impact others.

I, like many singles, am truly grateful for the phone calls, dinners, outings with other's families, concern and love shown to me by my married friends.  However, each person married or not, must find their own peace and joy.  No one can provide it nor does it come in an earthly relationship.

SHE SAID:  The same way you would encourage anyone who has desired for something, someone, anything in his or her life—no matter the time period.  You listen, you offer a shoulder to cry on, you pray with and for them (Galatians 6:2).  You walk with them through their sadness and suffering, pointing them to the Father and toward his timing and plans for all of our lives.  We don't always understand his higher ways, but we do understand that he is sovereign and causes all things to work together for his good (Romans 8:28).  This is the hope that we cling to and all that you or your friend or any of us can do in trying to understand different mystifying situations in each other's lives.

QUESTION:  I'm a 31-year-old male.  I have a female friend the same age who doesn't believe you have to date someone to get to know them.  She believes God will reveal to her the man she's to marry at the right time.  Not quite knowing how to ask out someone like this, I asked if she wanted to court—she said, "Well let's go out!"  We've had dinner twice and she says she definitely wants to do it again, but the times we "hang out" are here and there, dependent upon her schedule.  Because of her full calendar I'm always hesitant to call her, but when we do talk we have good conversations.  Another female friend of mine says it could take two to three months for her to decide whether or not she actually wants to date.  How do I handle this nebulous, "friends stage"?

HE SAID:  I have to agree with your friend, you don't have to "date" someone to get to know them.  You can learn a lot about a person by being around, listening, observing and seeing how they interact in different situations. 

Try not to get caught up in the "terminology" of whether or not you are "dating."  You have gone out with her a couple of times, and she is still around.  Continue to ask her out, leave her messages, and let her know how serious you are about spending time with her.  She may just have a full schedule because she hasn't had anyone in her life she was interested in enough to change it for or maybe she wants to see if you will pursue her.

SHE SAID:  Okay, well personal definitions of "dating" and other mixed messages aside, what is the standing of your heart at this point in the "friends stage"?  Are you all in?  Or are you only mildly interested and invested?  It sounds to me like you are more than mildly interested in pursuing a serious relationship and aren't letting her "schedule" or fluctuating point of view when it comes to more-than-friends relationships sway your intentions up until this point.  However, it also sounds like you might be concerned that she is not as interested in you as you are in her—or you might not have sent in your question for us to answer.  If this is the case, then I would suggest slowing down a bit and letting your female friend have her two to three months of decision time to figure things out on her own.  Meanwhile, you will still be around but will be observing from a more careful distance, as you step up your internal guard's ground patrol of your heart just a little bit.  Watch, wait and pray.  Then see what God is telling you and showing you about the situation (Proverbs 18:15).

QUESTION:  I would like to know what are God's "rules" on women initiating a relationship with a guy.  I've been challenged on this subject as a leader, and I guess I just assumed through my upbringing and culture that a woman should never call a guy and initiate the relationship.  In studying the Bible I can't really find anything that suggests this, but I believe that in today's world as soon as we take our eyes off Christ, our strong tower begins to weaken and if our eyes are not on him, sin will begin to creep in on whatever we have our eyes on.  I believe God created man as the initiator and the woman as the responder, but I am having a hard time finding scripture to back that.  I have no problems reevaluating my view on the subject and just want to know what God says.

HE SAID:  "The head of every man is Christ, and the head of the woman is man" (1 Corinthians 11:3).

Woman was created from man as a help mate for him, not to lead.  When those roles are circumvented or not exercised, possibly by men not taking the initiative to pursue or women not wanting to wait, an imbalance occurs in how God created man and woman to operate. 

There's nothing wrong with a female initiating a conversation or showing interest in a man, however I caution women who take a more assertive role to understand this could be an indication of or facilitate a character trait of a man who may not be capable of leading in the relationship.

SHE SAID:  Look to the different relationship examples that we have been given in Scripture for clues:  Isaac and Rebekah (Genesis 24), Jacob and Rachel (Genesis 29), Boaz and Ruth (Ruth 1).  In each story, the woman was sought after or noticed by or pursued by the man.  However, the example of Boaz and Ruth has a unique twist related to that time period and the culture.  Naomi instructed Ruth to request that Boaz act as her kinsman-redeemer, but it was Ruth's right to do so according to levirate law (if a woman's husband died, his next of kin was to take her as his wife and protect her).  Boaz, however, inquired about Ruth first, made provision for her and approached her first in his fields.  Also, back in Genesis, even Adam was the one who first noticed Eve (who God created for him and brought to him) and said:  "This is now bone of my bones and flesh of my flesh; she shall be called woman, for she was taken out of man" (Genesis 2:23).  Thus, in my interpretation, it was Adam who defined the relationship and sought to claim his partner—not Eve.  ‘Nough said.

QUESTION:  A godly single man prays for a wife!  His mother has moved in ten years ago to help raise his two boys and she hasn't moved out!  The boys are 22 and 23.  God has brought him his wife, but confusion about his mom (who's moving in and out) has caused them to break up!  How do you date a 45-year-old man with his mom living at home?

HE SAID:  Unless strict boundaries were pre-determined, by allowing his mother to move into his house, this man has empowered her to continue the mothering process not only to his now grown boys, but also to himself, and you will be probably always be looked upon as the reason she is being asked to leave.

You can share your thoughts, give him an ultimatum, befriend his mother or live with it, but ultimately it is his decision on how to proceed with his mother and yours to continue with the relationship or not.

SHE SAID:  You would relate to him in the same way you would if you were already married to a 45-year-old man whose mom is living with the both of you at home.  Let's say, for example, that his mother moved out of the house.  Permanently.  She got her own condo or place or whatever.  And then you and this man get married.  A year later, his mother (now she's your mother-in-law) has an accident and cannot live alone any longer.  So the man decides that he will care for his mother in his home, and she moves back in (Exodus 20:12; 1 Timothy 5:4-8).  You are faced with the same situation here.  If you cannot see yourself ever living with a spouse and his mother, then perhaps you should not ever get married.  It could happen.  We never know what life will bring our way or how our circumstances will be changed or not from one day to the next.  Now that this man's sons are grown, perhaps this man is simply looking out for his mother and wants to provide for her in terms of a dwelling, in terms of safety and in terms of companionship. If that is the case, then hats off to him for taking care of a family member. 

But beyond the practical issues here though, I also wonder if your question doesn't also indicate that there are some deeper maturity or emotional issues that are going on.  Is the man fully healed from whatever happened to the mother of his two sons?  Is he widowed or divorced?  Was he ever married to the mother of his children?  Perhaps he still needs to work through some issues from whatever has happened in his past.  Or is he clinging to his mother in an unhealthy way and therefore cannot move on toward a healthy relationship with a spouse?  Sounds like this needs to be talked out in order to uncover the root issues and find out what is really causing trouble in the relationship—for either this man or for you.

QUESTION:  Is it right to reject a man because of his poor work ethic and inability to motivate himself to prepare to provide for a wife?  I am a youthful 48 years of age and he is 44 and have known him as a friend for many years.  I am at the stage in my life where I would like a break from the regular routine of full-time work and be able to just work at being a homemaker and perhaps work part-time at something that I enjoy doing.  Sometimes people don't understand my viewpoint because we live in an age where women are career people and sometimes earn as much if not more than their husbands.  Many women do not want to stay home.  If I really loved this man shouldn't I be able to deal with this?  After all, the marriage vows do say "for richer, for poorer" and who is to say that any future man may not get sick or lose his job?  I guess as time goes on and this guy remains in my life I wonder if I am letting an opportunity pass me by.  I had someone ask me if I expected to marry a man and just live off of his nest egg?  I took offense to this, because I believe I am worth any man's nest egg!  I will be giving my future husband my life and would like to think that he would be more than willing to look after me financially.  Thanks for your input. 

HE SAID:  Each of us must decide what we need, what we are looking for and what we are willing to give up in a relationship.  I see a successful relationship as one plus one equals three.  It brings two people together to make each person better than they can be alone. 

A relationship does not mean sucking the life out of the other nor having to contribute equally in all areas of the relationship—financially, emotionally, spiritually, caretaking, etc.  The roles and portion each contributes can and probably will change as their seasons together changes.

A 44-year old who still has poor work ethics and is unable to motivate himself will probably struggle personally and especially relationally. 

SHE SAID:  Yes, if you loved this man in the way that you should in order to proceed toward marriage, then his "poor work ethic" would not be an issue for you.  It wouldn't even faze you, because your love would cover this or minimize it and not cause it to be a problem for you.  But because it is, then that should give you pause.  He is who he is, and you cannot expect that he will change once you are married or will someday be who you wish he would be to meet the desires or criteria that you have when it comes to a husband-and-wife relationship.  If ambition is important to you when it comes to a mate, then you need to keep looking for someone who is better suited for you.  Yes, you could find a husband who is ambitious, and he may lose his job down the road.  But his ambitious nature is not lost, right?  It is still there.  Having that kind of a quality or characteristic means that he will likely do whatever it takes to provide for you and make sure that you are protected and are not having to work full-time (if he can at all avoid this). 

You are also right in that anyone can change in any way at any time.  There are no guarantees in life.  In relationships.  In marriage.  In anything.  You are probably not the same person you were five years ago, and neither am I.  We are always changing (hopefully for the better).  But we should still not just throw caution to the wind, check our senses at the door and marry just anyone without some due diligence and prayer.  I don't find any fault with you at all for being so careful and searching your heart to see what it is that is important to you in a mate.  One criterion that I have is this:  does this man make me laugh or does he "get" my sense of humor?  Some might scoff at that and think I'm waiting around for the next Jerry Seinfeld or something, but to me it speaks to something much deeper.  If we are on the same wavelength when it comes to personal styles of humor and to what either of us finds funny, then that tells me that we have a good chance of being in sync with each other in the more crucial areas of our lives as well (Philippians 2:1-2).

HE is … Cliff Young, a contributing writer and a veteran single of many decades.  He has traveled the world in search of fresh experiences, serving opportunities, and the perfect woman (for him) and has found that his investments in God, career and youth ministry have paid off in priceless dividends.

SHE is …
Laura MacCorkle, Senior Editor at  She loves God, her family and her friends.  Singleness has taught her patience, deepened her walk with the Lord and afforded her countless (who's counting anyway?) opportunities to whip up an amazing three-course meal for one. 

DISCLAIMER:  We are not trained psychologists or licensed professionals.  We're just average folk who understand what it's like to live the solo life in the 21st century.  We believe that the Bible is our go-to guide for answers to all of life's questions, and it's where we'll go for guidance when responding to your questions.  Also, it's important to note that we write our answers separately (we think they sound eerily similar sometimes, too!). 

GOT A QUESTION?  If you've got a question about anything related to living the single life, PLEASE SUBMIT HERE (selected questions will be posted anonymously).  While we are unable to answer every inquiry, we do hope that He Said-She Said will be an encouragement to you.

**This column first published on September 30, 2010