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.