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Should I tell my guy friend how I feel about him?

We are best friends. Should I tell him how I feel?


I have a great friend I have known for over two years. I know him very well. We attend the same church, share not only the same core beliefs, but also are aligned on many of the secondary and tertiary issues. We both enjoy our friendship and spending time together in group settings. We both consider the other a “best friend.”

For me as the girl, there is no man who makes me laugh like this guy, who I respect as much as him, and whose character is as upstanding and unquestionable. As it stands, we have even had a conversation addressing the elephant in the room: why we have never dated.

For me, there are no “romantic” feelings mostly because I know he is not interested, so I have kept them at bay, knowing that they could easily be awakened if he were to ever initiate and see me as something more than a friend. But even when another guy comes along, the thought that if I were to date someone else that we would not be able to share the close friendship that we have now is not something I can really comprehend. I don’t want to go without it.

To clarify, there is no confiding of inappropriate things or one-on-one time spent together. I just mean that if I were dating someone, I would not be comfortable with him having this level of ease and comfort, of familiarity and “chemistry” with another woman.

It kills me to never know. Couldn’t we just make this work? We are best friends! Is there ever a time when it would be appropriate to ask, “Why don’t we just try this?” or ask him if there really is no chance he would ever want more. I hate sounding so desperate, but more than anything, the thought of losing his friendship for a potential other person is difficult. I know that could change if the right person came along. But that is still not good! Ugh. Help! What do I do? I am at my wit’s end.


Thanks for writing. I recognize your question in part because it’s one of the most asked questions I’ve received in the past decade of writing this column, but also because it sounds a lot like what I experienced with Steve before we started dating.

“We should get our families together for vacations someday when we’re married.” That’s what he said to me, about us, about us vacationing together, with our future spouses and children. He said this to me at the height of being best friends but not dating. I wanted to scream: It would be so much easier to vacation together if we just married each other! Instead, I thought it loudly in my own head. I held my tongue. And I think you should, too.

This doesn’t mean that you should just continue on as you have been these past two years. On the contrary, I think a change is overdue. But how you go about doing this is critical.

If you simply blurt out the question: Why don’t we just try this?! Or ask him if there really is no chance he’d ever want more, you’ll short-circuit God’s design for his growth in masculinity. “It’s the man’s job in a relationship to bear the burden of initiating.” That’s how our pastor, John Kimbell, put it in this week’s installment in the biblical dating class he’s teaching at our church.

That doesn’t mean you don’t have an active role to play, and it might even include asking him what his intentions are toward you. But the best next thing to do, starting now, is to ask yourself how you’re helping maintain this status quo of being best friends but not dating, over such a long period of time.

In my situation, I was glad for all the time Steve spent with me and welcomed the long conversations over coffee, the shared enthusiasm for good books and politics, the joint effort to launch a webzine. I talk about this and more in Get Married: What Women Can Do to Help It Happen. I had helped build the friendship-to-nowhere, and I needed to help it change course.

Rather than take the lead and suggest we start dating, however, I asked him, in so many words, what fathers the world over used to ask on behalf of their daughters: “What are your intentions?”

You see, when a friendship between a man and a woman is different from all other friendships, when you think of each other as your closest confidant and the one you’d most like to spend time with, when you think of each other differently than you would your brother/sister, it’s time to come clean: This is more than a friendship. Regardless of what you call it, the relationship has the markings of a growing affection that isn’t shared with anyone else. The fact that you know your current friendship would be inappropriate if you were dating someone else is evidence enough that this is more than just friends.

It’s simply not possible for a man and a woman to share an intimate, unromantic friendship for long, if at all. Richard and Shannon Phillips, authors of Holding Hands, Holding Hearts: Recovering a Biblical View of Christian Dating, say:

…if you are part of a nonromantic male-female couple who enjoy each other’s company and are emotionally connected, and yet neither of you has romantic aspirations for the relationship, you are the first one of these we have ever encountered in years of experience with Christian singles (121-22).

As crazy as this may sound, your close friendship may be why he’s not asking you for a date. He already has the emotional connection, your loyalty, your companionship, and the relational security that typically follows from being in a dating relationship. The way to help him recognize the need to clarify his intentions is to stop providing what he should have to make a commitment to receive.

This is what I did with Steve. And that zany idea of joint family vacations helped me wake up to the danger of continuing on as his best friend without asking for the clarity of what our friendship meant. We had the friendship of a dating couple, but we weren’t dating. Once I realized my peril — of wasting my dateable years and frittering away any hope of dating him or anyone else for that matter — I asked him to clarify: What are your intentions? But — and this is key — depending on what he answered, I was willing to walk away.

If you ask a similar question and he says, “Oh, we’re just friends” or something similar, you will necessarily have to change the way you relate to him. The next time he asks you to do something with him, as friends, the way he has been these past two years, don’t just say yes. Ask him simply, “What will this mean?” He’ll likely reply, “Huh? What do you mean?” And then you can explain that “there is no man who makes me laugh like you do, none I respect as much as you, and whose character is as upstanding and unquestionable as yours. I don’t want to merely go on as we have been, as buddies.” Then let him speak next. The silence may be long and awkward, but it’s essential that you get out of his way so he can lead. This is the point of no return. If he rebuffs you, you will need to stop relating to him as best friend. But you should stop doing that now, even if the opportunity for this conversation doesn’t happen for a week or more.

It’s time for you to interrupt the inertia of your friendship with this young man. Stop doing the same things while hoping for a different result. The best option is to scale back your friendship. It will be having less of you — not more — that may wake him up to the good gift he has in you. Then, if he asks you where you’ve been or why you’re so detached, you can help him see what you’ve realized: that your friendship is more appropriate for a couple that’s dating. As much as you enjoy being best friends, you know that such intimacy should be reserved for dating couples and especially, those exploring the possibility of marriage.

Pray for your friend. Ask God to give him Spirit-fueled boldness. Resist the urge to fill the leadership vacuum — God can use the tension it creates to motivate him to act. To do otherwise is to help him keep being passive. I will pray for you.



Copyright 2015 Candice Watters. All rights reserved.

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About the Author

Candice Watters

Candice Watters is the editor of, a weekly devotional blog helping believers fight the fight of faith by memorizing Scripture. She is the author of Get Married: What Women Can Do to Help it Happen. In 1998, she and her husband, Steve, founded Boundless.


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