Dear Libby,

I’m a 25-year-old man who lives with “Jake” (26), “Sally” (29), and “Anna” (25). We were all friends back in high school, and after me and Anna finished college, we decided to rent a house together in town. We’re a very tight-knit group, and we all agreed years ago that it would be a mistake to have any romantic entanglements between us.

We’ve all had a variety of significant others throughout the time we’ve known each other, but none of them last more than a year or two. Right now, me and Anna are single, Jake has a casual relationship with a woman from work, and Sally is dating a guy she met on a hike six months ago.

The problem I’m having now is that I realized I’m falling for Sally. She’s so smart and funny and has great taste in music. She’s amazing. I’ve always been the closest with her out of everyone in the group. We’ve shared stuff about ourselves that even our families don’t know. When one or both of us have a partner, we go to each other for advice or to vent. Our friendship has always been rock-solid, but these new feelings I’m having threaten to ruin everything.

Last night, Sally confided in me that she’s thinking about breaking up with her boyfriend. She asked for my opinion on the matter, as she’s done a hundred times before. In the past, I’ve always been honest about what I think. Sometimes she heeds my advice, sometimes she ignores it, but she always appreciates it because she knows I see things she might not.

I’m having a dilemma about what I should do. I told her to let me think about her question and get back to her, but I can’t keep putting it off. Her boyfriend is actually pretty great, and they compliment each other really well. He just got a new job in Atlanta, and he asked her to move there with him. Neither of them want a long distance relationship, so her options are either go with him to Atlanta or break up with him and stay here.

The selfish part of me wants her to stay, but deep down, I think the right decision would be to go with him. She can easily get a job in Atlanta, and she’s always loved seeing new places and meeting new people. I think her and her boyfriend could have a great life together. They’ll probably get married and have two kids like they both want. But I don’t want to lose her. I want to be with her.

If I tell her I think she should go, I know it’ll kill any chance I have of being with her. If I tell her I think she should break up with her boyfriend, there’s no guarantee we’d get together, and I’ll have convinced her to give up what could be her soulmate for nothing. Jake and Anna are divided on what she should do, so I know my opinion could sway her one way or the other.

What should I do here? I’ll be miserable without her, but what if she ends up being miserable because she broke up with him? Should I just tell her how I feel and see if she feels the same way? What if I tell her and it ruins our friendship? If I tell her she should go with him, even though she’ll be far away, we’ll still be friends. Is friendship the best I can hope for in this situation?

–Living With Heartache

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Dear “Living With Heartache,”

This is a very complex issue. It seems to come down to whether you value your own happiness over Sally’s. Of course, as you said, there’s no guarantee that convincing her to stay will bring you happiness. Your feelings for her won’t just disappear, so if she isn’t interested in a relationship with you, you’ll still end up brokenhearted.

The best thing you can do is be completely honest with Sally. Tell her what you told me about how you see her relationship with her boyfriend, and that you believe they will go the distance if she moves to Atlanta with him. Then tell her you’ve fallen for her, and those feelings are making you want to selfishly agree she should break up with him.

There’s a very good chance your friendship with Sally won’t survive. She’ll view you in a totally different light once she knows you’re in love with her. But if you truly care about her as a person and want her to be happy, you have to make that sacrifice. If by some miracle she’s been hiding reciprocal feelings for you, this will be the best opportunity for her to tell you about it.

Ultimately, your dilemma is merely a symptom of our ever-changing lives. As great as it is that you and your friends have remained so close and even live together, all friendships and relationships evolve over time. I doubt the four of you will still be living together ten years from now. Even if Sally stays, she might end up meeting someone else down the line. Jake and Anna will, too. One by one, you’ll move out and move on to the next phase of life. There’s a good chance you’ll meet someone else and end up moving on as well.

I genuinely sympathize with your situation. It’s a terrible burden to bear an unrequited love—especially when it’s for a longtime friend. You’ve already diagnosed the problem and laid out the motives behind why you’d tell Sally to break up with her boyfriend, as well as your true opinion about their relationship. It sounds to me like you already know what you should do. Hopefully this push from me will give you the strength to actually do it.

Good luck my friend. I wish you nothing but the best. I believe you’re a good person, and you’ll eventually find your own soulmate. Even though that soulmate won’t be Sally, I think you’ll realize giving her up was the best course of action for both of you. When you look back on this situation, you’ll be able to see how your decision was the first step on the road to true happiness.

–Lovingly, Libby