How can we transition from being friends to dating?

Question

I know Boundless has a lot of articles about being buddies with the opposite sex and how you shouldn’t be super close with your opposite sex friend unless your intentions are to date her. But I had a question on how to go about dating your best friend.

Here is the basic scenario: What if you have been long-time friends with a girl for three years and recently you started seeing her in a new light? We already hang out either with a group or alone pretty often. How do I go about transitioning? And how do I find out how she feels without making it awkward?

I feel that in the end, we would eventually need to talk about our intentions because hanging out alone now may feel like a date to me because of my change in feelings, but to her it probably is “just friends hanging out” unless she secretly likes me, too.

Answer

Two thoughts occur to me. First, I like the idea of a dating relationship having some friendship history. If a dating/courtship relationship is anything, it should be an amazing friendship. Second, three years of close, opposite-sex friendship has created a context that will require very careful navigation. Trust me, there already is a relationship, and something significant is about to happen to it. By all means, though, it is past time to do something, and God wants to work it for everyone’s best and His glory.

You’ve already read our articles about opposite-sex buddies and why we caution singles to be very careful about them for a variety of reasons. One of those is what you’re now experiencing: Given enough shared time and enough shared emotional energy, it is virtually impossible for stronger feelings not to develop. That’s great if it happens to both at generally the same time, but when only one of you begins to “fall,” the friendship is on an unavoidable track to change. But when “buddy” feelings start giving way to deeper heart feelings, it is rare to ever go back to “buddies.”

I advise that you have “that” conversation with her. There is no special secret to it; you just have to do it. As I have told many readers who’ve asked, “But what do I say?” you simply tell the truth.

Yes, it could be awkward. Yes, you will probably have knots in your gut. Yes, it could go either way. But it won’t be nearly as difficult as not saying anything and trying to stuff your feelings and emotions, especially when you’re around her. You have to do this. It wouldn’t be fair to either of you to if you didn’t.

It could be that, as you mentioned, she has had the same thoughts and is favorable to the idea. Wonderful! It will be a little weird at first, but that will eventually smooth out when you both get used to the idea.

It could be that the whole concept is a bit of a shock to her and she’s not quite sure what to do with it. That’s OK. Give her some time to think it through, but she does need to know that for you, there is no going back to “just friends.” Your heart has already made that decision for you, and not moving forward still means change, and probably one that will be difficult. She needs to know you simply can’t be close “buddies” anymore. For one, your heart can’t take it, and two, your close friendship could very well be keeping both of you from pursuing a relationship God might have for you with someone else.

Scripture says in John 8:23 that, “The truth sets us free.” And while in that specific context those words refer to Jesus, the truth of that phrase has wide application. The truth is, you’re starting to love her as more than a buddy, and there is absolutely nothing wrong with that. It’s perfectly normal, and we might be surprised if after three years it didn’t happen. So tell her the truth, and trust God to honor it.

Blessings,

JOHN THOMAS