Christian Singles & Dating

He Said-She Said: Can Friends Who've Dated Be Friends Again?

  • Cliff Young & Laura MacCorkle Contributing Writer & Senior Editor
  • Updated Sep 24, 2008
He Said-She Said: Can Friends Who've Dated Be Friends Again?

:  Each He Said-She Said column features a reader's question with responses from a male and female point of view.  If you’ve got a question about anything related to living the single life, please submit here (selected questions will be posted anonymously).

QUESTION:  Not too long ago, my best friend and I agreed to date.  At that point, I realized that my emotions were well invested in this relationship—no matter what kind it was (friendship or dating relationship).  But our dating relationship lasted only four days.  He called me and told me he realized his motives hadn't been what they should be; he thought he would lose me as a friend if we didn't date.  And so now we're not dating, and I'm confused.  What do I do?  I have seen what a dating relationship with him could be like and have found that I have deeper feelings for him.  I'm also angry because he didn't give prior thought before asking me to date him.  Should I just walk away from the friendship?

HE SAID:  Growing up with no sisters, I have enjoyed having female friends.  There are some (maybe a lot of) things that guys don’t know about women or ever will without the (loving) instruction from a female.  (I just heard a resounding “Amen.”)  I won’t try to speculate on your friend’s background or intention, but will try to share some thoughts based upon your question and my experience.

Several times in the past I considered trying to move a close friendship with a girl into a dating relationship.  I understood this could possibly “jeopardize” the friendship and weighed the options heavily.  It was a difficult decision each time and did result in a lost friendship a couple of times.  These experiences led me to think about the differences between a friendship and dating relationship:

In a friendship, there are no specific expectations; in a relationship, there are many expectations (and assumptions).

In a friendship, “going out” doesn’t need any advance notice; in a relationship, there should be “advance” notice (at least at the outset).

In a friendship, paying your own way is norm; in a relationship, a guy should (usually) pay.

In a friendship, there are no specific commitments; in a relationship, there should be a commitment.

Were any of these factors discussed prior to or during those four days of dating?

His motives hadn’t been what they should be …
If your friend only wanted to “date” you in order to keep the friendship, maybe he isn’t your best friend.  By this, he seems to be only concerned about his own needs (maintaining the friendship and companionship) and not yours (relationship).  Close friends are concerned about the other’s well-being. 

He thought he would lose me as a friend if we didn’t date …
Did you ever make mention or hint to him that he would lose you if you didn’t date?  If this was never discussed and he formulated this in his own mind, he isn’t ready for a relationship.

I have seen what a dating relationship with him could be like …
What have you seen?  Based on what you have mentioned, he appears to have some fears that need to be addressed and isn’t sure as to what he wants.  Are you selling yourself short of what you want and deserve or what is God’s best for you?

I have deeper feelings for him …
What kind of feelings?  What are those deeper feelings based upon?  It sounds as if you both enjoyed each other’s friendship and companionship prior to establishing it as a “dating” relationship.  Since you called him your “best friend,” I am assuming that you have spent a great deal of time with him in person and on the phone and as a result, you may have grown close to each other in ways that resemble a dating relationship.  However, a relationship should be based upon honesty, trust, values, and communication.

I am angry because he didn’t give prior thought before asking me to date him …
Again, this comment leads me to conclude that he doesn’t care about you or your feelings.  Why would you want to be with a person who puts his feelings above yours?  Do you think that will change once you start dating?  Do you think that will change if you get married?

How did the discussion of dating come up?  Was there any talk about what would change going from a friendship to a dating relationship?”

I have found Christians to be some of the most dishonest people I know.  Not because they steal things or take advantage of others, but because they lie about their feelings. 

— Donald Harvey, Ph.D. in Marriage and Family Therapy and author of

As Christians, we often hurt ourselves and others in relationships by not being honest about our feelings.  Paul tells us to, “put away falsehood and speak the truth with one another” (Ephesians 4:25).

Back to your questions of what you should do and should you walk away from the friendship?  I believe only you can answer these questions for yourself, after much time in prayer.  I also feel that you already know the answer.

SHE SAID:  Speaking the truth in love.  That’s Paul’s instruction to believers in Ephesians 4:15, right?  It’s how we grow together in the faith and how we are unified as members of the same body.

But it’s a hard thing to do.  Still, I sure wish your best friend had done this before you unpacked your bag—and your feelings—on your four-day trip in the “Promised Land of Dating.”

Beyond dating relationships, though, truthfulness is a quandary we all face each and every day:  Is it more important to say or do what someone wants to hear or wants you to do or is it better to say to others or do what is honest and an accurate portrayal of your thoughts, feelings or intentions?

It’s really the difference between conveying falsehood or truth.  If we think about it in those terms, then it gets real clear, real fast.  It’s no longer about “I didn’t want to hurt her feelings and tell her that I didn’t want to date her.”  It’s now about “If I say this, then I am dishonest because it is not truthful.” 

The truth was very important to Jesus.  Looking through the New Testament, I found that Jesus said “I tell you the truth …” over 70 times.  Now, I realize that the Gospels are accounts from different authors who related many of the same events, so maybe Jesus didn’t actually say this phrasing this exact number of times.  Still, even if he had only said it twice, words that are repeated from the mouth of our Savior are important indeed!  And it’s obvious that truth is a big deal in the rest of Scripture, too, and should also be for anyone who is concerned about modeling their lives after Jesus.

Now I don’t know all the particulars of your situation, so my answer may sound a bit on the harsh side up until this point (and probably even beyond this paragraph, for that matter).  But also keep in mind that any time a wound gets examined, it’s bound to hurt a little bit.

On one hand, your best friend may just be scared, have mixed-up motives and need some time to think about a dating relationship with you and viewing you in that context.  Perhaps he just really didn’t know what he didn’t know until he started dating you for four days. 

But in my experience, here’s what I’ve learned:  in most cases a man knows very early on (oftentimes from the moment he meets you!) what he wants.  If interested, then he knows that he knows that he KNOWS he wants to have a dating relationship with you.  And he is focused and makes a concerted effort in seeing this come to fruition.  There will be no doubt or question about his intentions, as he will make it abundantly clear

If a man does not know if he wants to date you or not, then he will only have a friendship with you and will be careful to keep everything inside of the “platonic box.”  If he does know that he only wants the benefits of intimacy (emotional closeness) and no strings attached (no commitment), then he will only have a friendship with you.  The latter kind of friendship (or “free-lationship” as I like to call it, since one of you is not paying the price and one of you definitely is) is not in your best interest at all.

More of what I don’t know about your relationship is how long you have been friends (Since you indicate that he is your “best friend,” I’ll assume that you’ve known each other for a while and have experienced some life together.  And if that is the case, then it could be argued that your best friend should have known you well enough to know what it would be like to date you before asking you to do so.).  Also, did your best friend ask you to date him with no encouragement or pressure on your part?  Or did the switch suddenly flip one day, and he saw you in a different light and decided to pursue you as a romantic interest on his own?

At this point, I would say that you are resting uncomfortably at “Awkward Impasse.”  What to do now that your best friend knows you have romantic feelings toward him?  What to do now that you know that your best friend does not apparently feel the same way toward you?  Once you’ve crossed the line of friendship, it is very hard to go back to just being friends again. 

Going forward, if you do remain best friends what will happen when one of you starts dating someone else?  Will you be able to maintain your friendship?  Will you be able to protect yourself, so that you do not get hurt if he begins dating another, directs most of his attention elsewhere and spends less time with you?

It appears that your best friend doesn’t know what he wants, but you do.  You want more than a friendship.  My advice?  Put some space between the two of you and make yourself available to others.  There could be other quality men in your life who know what they want and are interested in dating you.  But right now they might assume that you are taken because of your “friendship” with your best friend. 

Also, a little time away from your best friend may help you to see the situation with new eyes and a little more clearly—and help you emotionally detach and protect your heart. 

“There is a time for everything, and a season for every activity under heaven,” said a wise man named Solomon (Ecclesiastes 3:1).  I know that God will show you the wonderful (and the best!) plans that he has in store for you.

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,’s Senior Entertainment Editor.  Since she’s only lived in four states in the continental U.S. and dipped her toes in just two oceans, she would one day like to experience life abroad … preferably where the views are lofty, the food is tasty and the shopping is cheap-y.

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.

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 July 3, 2008.