Dear Kathy and Katie,

I’ve been dating this guy for about eight months. It was great at first, but lately I’ve been thinking that we should see other people. I’m not sure how to tell him this without hurting him. He’s also a good friend of mine, and I’m afraid ending things will damage the friendship. But I can’t keep pretending I want this relationship to continue.

How do you think I should handle this?

-Anon

Dear Anon,

You’re certainly in a tough situation! Relationships–especially in high school–are very difficult to navigate. It can be hard to break the news that you’re not interested in someone anymore.

For starters, make sure you tell him face-to-face that you want to end things. Breaking up over the phone or over text may seem like an appealing option, but it will invalidate the other person’s feelings. It may be hard at first, but explaining why you don’t think your relationship is working while actually facing the person will make the discussion easier.

Make sure he understands why you feel you should break up. We’re not sure if these feelings of doubt are one sided, but it may come as a surprise to your boyfriend! You’re not obligated to explain why you don’t feel it’s working out, but it will help preserve the friendship.

Now, as for the trickiest part of your question: the friendship may or may not last. It depends on a variety of factors.

If you guys were friends for a long time before you started dating, it may be difficult backpedaling to that point. Your relationship has crossed a boundary, so to speak, and it can be hard to cross over that line again. Your boyfriend may still have feelings for you, which could be hard to reel back to the point of “just friends.” On the other hand, after your long friendship, your boyfriend may find it easier to become friends again; he values you as a person as well as a romantic partner.

If you two were friends for only a short time before you started dating, it may be easier. You two wouldn’t have had years to develop a friendship/relationship so complex, so it would be easier to “start over.” However, he may be spurned to be demoted after a “trial period.”

It really does depend on your boy!

You should expect him to be upset after you break up with him. You may have to give him a few weeks for him to come to terms with everything, considering how long the two of you have dated. Ask if he would ever consider still being friends after letting him cool down.

I hope everything works out! Remember that while you should be worried about your boyfriend’s feelings, your own emotions are equally as important. If you don’t feel satisfied with the relationship anymore, don’t try to make it work. Be respectful, but firm.

Best of luck always,

Kathy and Katie

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