Courtney Kissinger

Best Friend or Boyfriend?: Should You Tell Him You Like Him?

Q: I’ve been best friends with a guy for awhile. But now I feel like there could be something more to our relationship. I am scared to tell him how I feel, scared to ruin our awesome friendship… yet I feel so ready to be in a relationship. Should I tell him how I feel?

A: As we (women) enter our dating years, having a guy who is our best friend can become a tricky thing. Our natural maternal instinct is to care for others and to be compassionate and understanding. This can lead to us giving and giving of ourselves, and not expecting as much in return. Without trying to manipulate us, guys can take advantage of our caring nature. Guys can enjoy all the benefits of having a best friend who is a girl (aka, not a girlfriend) without having to commit to a dating relationship. They have someone they can call if they want to talk (or not, because they’re not dating), someone they can always hang out with (or not, because they’re not dating), someone to ask what they should wear (or not…) — all while keeping their eyes peeled for someone who they do want to date and commit to.

So what’s a girl to do if her best friend is a guy?

1. Guard your heart.

Proverbs 4:23 tells us, “With closest custody, guard your heart, for in it are the sources of life.” As you move closer to marriage (eg, he’s proposed, you’ve said yes, and you’re preparing to build your lives together), you will be able to reveal more of your heart. It’s perfectly okay to keep these parts of your heart guarded until you’re sure he’s committed to you.

2. Consider some distance.

Yes, it’s hard to hear, and I’m probably not the first to tell you that backing away may be beneficial. Not just beneficial for you (so you’re not constantly giving of yourself without receiving in exchange), but also for the guy. Distance from you may help him realize what he needs to do. Maybe he needs to do some maturing on his own, or maybe he’s ready to commit to you in dating relationship.

3. Let the guy do the pursuing.

If the guy is not taking action in telling you how he feels and asking you to be his girl friend, there’s a reason for it. If we, as women, initiate the relationship it may be hard for the guy ever to take that leadership role. And trust me, as someone who has experienced both, it’s a lot more fun to be pursued than to do the pursuing. Instead of trying to convince a guy that you’re worth dating, wait for a man who is already convinced of that.

4. Be realistic.

Whether he starts dating someone first or you do, your relationship will eventually change. Time spent together, open communication, and inside jokes that you share are going to be replaced by someone else in his life or yours. So try to keep your current friendships in perspective. Appreciate the friendship as a gift from God, but don’t expect it to be a lifelong best-friend level relationship.

As we try to navigate the muddy waters of high school relationships, keep in mind that God wants our happiness, even more than we do. Expect big things from Him. If you’re ready for a relationship but no one’s knocking at your door, be patient. Continue to talk, listen, and give your heart to God; He’s the one best friend you can count on to always be there.

Do you have a question about dating and relationships you’d like to ask Brian and Courtney Kissinger? Email them at [email protected] and your question could be the next blog post!

Courtney Kissinger

About the Author

I graduated from law school and then decided to become an elementary school teacher. I’m married to an arguably attractive youth minister, Brian, and we have the cutest daughter. I hate cheese. That includes cheese on pizza, Nacho Cheese Doritos, cottage cheese, and cream cheese. I will eat cheesecake if it’s covered with chocolate.