EDITOR'S NOTE: He Said-She Said is a biweekly advice column for singles featuring a question from a Crosswalk.com reader with responses from a male and female point of view. If you've got a question about anything related to singleness or living the single life, please submit it to hesaid-shesaid@crosswalk.com (selected questions will be posted anonymously).

QUESTION: One of my best friends and I have been friends for many years, dated on and off, had our ups and downs, made mistakes, mis-communicated, apologized, and revitalized our friendship. He recently told me that I am one of his very closest friends, and that he doesn't feel deserving of the friendship I give him. It meant the world to me. Would it be appropriate for me to bring up the topic of a relationship and express my romantic feelings toward him? Part of me thinks he deserves to know, but another part believes he needs to be the man and step up in that area. Am I belittling him if I initiate it? I really want to respect him as a man and not pressure him in any way.

HE SAID:

After all you seem to have gone through over the years I don’t understand why you would even need to ask this question. With him being one of your best friends and having the history you do, that should warrant the right to speak the truth to him.

However, just for everyone else’s sake, let me back-up and try to share my perspective from what I consider an “atypical” guy’s point of view.

I have been a proponent, especially when mentoring young men, of being good friends before starting to date since dating can complicate friendships (and youth groups). At the same time, I also feel when the relationship has moved forward to the point when your counterpart becomes an irreplaceable part of your life you need to let them know.

Your “friend” should ultimately take the lead (as the male) and initiate conversation, however, in some instances, they may not realize their “buddy” now has feelings which have grown past the “I just want to be friends” stage (which I have sometimes been suspect of). You can “wait for him” to bring up the topic, risking he never will (and forever wonder “what if?”) or you can share your heartfelt feelings (as I have also done) only to discover they are not reciprocated.

In either event, you will know and no longer have to play mental gymnastics.

My Best Friend’s Wedding may give you an entertaining perspective of a comparable situation. Julia Robert’s character agreed to marry her best friend, Dermot Mulroney, by a certain age if they were both still single, but didn’t want to go through with it until she finds out her friend was engaged. If nothing else, it may give you something else to think about.

You seem to have already made up your mind and just needed some prodding, so go do it. The worst thing that can happen is he doesn’t share your feelings; however the upside is that he does!

SHE SAID:

Thanks for taking the time to share your heart on this sensitive subject.

By all means you need to bring it up! Right now you are sort of in this in-between place, a place I like to call "friendationship" - a place that can quickly become dangerous. A place where your feelings are growing and his might not be. A place where you could get so hurt that you might not be able to salvage the friendship.

However, because you have been romantic before, you didn't mention what happened that kept you guys from moving forward. What has passed between you will affect your decision. Have you looked at the reasons it didn't work out before? Have you both dealt with those reasons? If you feel that you have, then I would support sitting down when you are both are rested with no distractions and let him know. I can tell from your letter you know he might not feel the same way, but at least you will know. You can then decide what to do.

Please know I have been where you are. I had the conversation and the guy didn't feel the same way. Although it was difficult to hear this, I was thankful because I knew where our friendship stood. I didn't have to wonder anymore. Please know, as with all relationship (friends or romantic), we need great communication. He may be thinking the same as you but due to your past together is thinking you just want to be friends. Go slow, keep praying, trust God, invite others to pray and hold you accountable.

Final thought: I do believe the man's role is to do the chasing, but I think it's the role of both to communicate. For most women you will know when a man is interested, so you can wait. But, with your mutual past together, I think you might be passed the chasing and need to just talk to each other.

As iron sharpens iron, so one person sharpens another (Proverbs 27:17).

HE is … Cliff Young, a Crosswalk.com 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 … Kris Swiatocho, the President and Director of TheSinglesNetwork.org Ministries and FromHisHands.com Ministries. Kris has served in ministry in various capacities for the last 25 years. An accomplished trainer and mentor, Kris has a heart to reach and grow leaders so they will in turn reach and grow others. She is also the author of three books.

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 twenty-first 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.

GOT A QUESTION? If you've got a question about anything related to singleness or living the single life, please submit it to hesaid-shesaid@crosswalk.com (selected questions will be posted anonymously). While we are unable to answer every inquiry, we do hope that this column will be an encouragement to you. Click here to visit the He Said-She Said archives.

Publication date: August 22, 2013