Last updated on October 22, 2020


Hi! I’ve asked a question before and I really appreciated the response. It helped me to start to become better. My question today is: when do you know you need to let someone go?

I have a friend that is more than a friend in a few ways, but he’s the only “friend” that I’ve ever had. When we first met I’d just gone through a breakup that I let really hurt me emotionally, so I guess I latched on to him. Well, I’m a teen so my feelings and what I know about the world are very different in composition, and he was there as my friend. We grew as friends and became more than friends, but we never were a couple although he’d asked me in the past.

To get a better understanding of the situation I’ll try to explain our relationship better. He’s about two years older than me and a grade ahead. He graduated this year, but we started being friends during my freshman year. Over and over again we have had arguments and complications. Every time we find ourselves together again. This has been happening for almost four years now and I’ve been so tired of it. Truly, I have tried to stop — truly I have. I have tried to stop talking to him, but when he contacts me or we make contact, I just can’t say no. I can’t say no to speaking to him or being friendly. I just can’t imagine that the person I was best friends with could act like that and not care about me still. I can’t say that I was near perfect. I said hurtful things when I felt like my feelings were hurt, just like he did.

Those things over the years have made us different. I believe in my heart that he still has that same person in him as he did when he “saved” me as a freshman. I see it in him sometimes. Sometimes he seems to care so much. When do I know that I should let him go? I feel like I know I need to, but I won’t. I try to get him to admit how he feels, but he avoids answering. I like him. Actually, I love him with all of my heart. So what do I do when I feel to the pit of my soul that he cares about me, but he won’t admit it?

I want to move on in life. I love him so much I don’t consider any other boys whatsoever. He cheats on all of his girlfriends. He says he “loves” them, then he leaves them to be with another person he “likes a lot.” It seems like common sense to leave someone like him alone, but something in my soul tells me not to. He has family issues. He tells me I don’t understand what makes him do the things he does. I want to help him feel better so badly, but he won’t let me. I can’t let him just die away. I feel like if I’m not there for him, he’ll wither away. How do I live for myself? How can I move on in life when he’s the only “him” I know and the only “him” I care about.


It almost sounds as if you think it is romantic to be miserable.

First off, it is natural for two people to drift apart when they are no longer sharing the same experiences. He has graduated, you haven’t, so it is typical of the differing experiences to cause a separation. Drifting apart is also typical during the teenage years. People’s tastes change — literally and figuratively. Just like the foods you enjoy now are not the same as those you preferred when you were young, so too the types of people you particularly like will change as well.

People also have a tendency to idealize the past. “Do not say, “Why were the former days better than these?” For you do not inquire wisely concerning this” (Ecclesiastes 7:10). We overemphasize the good things and minimize the bad things over time. You are doing this with your memories of your relationship with this young man. You know you’ve had your disagreements and fights, but they aren’t that important to you. You remember that he “saved” you and that has become the only real issue to you.

I do think you hit on a very important point at the beginning. You artificially limited yourself to one boy. You didn’t allow yourself to make friends with other people. Now that you and that one boy are drifting apart, you are panicking that there isn’t anyone else. What I want you to start concentrating on over the next several months is making friends with a large number of people — male and female. Not necessarily serious friends, but people whom you can say you are comfortable talking with and doing things with. That might demand that you swallow your shyness, but what I want you to aim at is finding ten people you enjoy being with. “A man who has friends must himself be friendly, but there is a friend who sticks closer than a brother” (Proverbs 18:24). The reason is that you need a more balanced view of relationships. Right now you have all your eggs in one basket and you aren’t seeing things clearly as a result. Don’t aim to live for just yourself. Right now, aim to live for several other people — not just one person — because that is more your nature.

One of the biggest mistakes women make in dealing with men is treating men like their women friend. I see you making the same mistake when you tell me “I try to get him to admit how he feels.” That isn’t how men operate. Women operate on feelings. Men rarely have the need to discuss feelings. I suspect that he has been telling you how he feels, but because it doesn’t match what you feel you discount it. Because he, as a guy, doesn’t discuss a concept at length, you conclude that he hasn’t made up his mind about the matter.

I’m guessing that from what you have written that he sees you as a good friend, but no more than that. He cares about you, but he knows he doesn’t want to spend a lifetime with you. You have these starry-eyed dreams of “rescuing” him, just as he helped you, but that isn’t what he is looking for in a potential wife.

Think about it from a more analytical view for just a moment. Try to imagine that you weren’t attached to him, but your best girlfriend was all moon-eyed over him. What would you tell her? Would you think that he would make a great husband? Do you think he would only love her for a while until another girl caught his eye? Would you think that an emotional roller coaster of a relationship was good for your friend? Often we can see things clearer in regards to other people than with ourselves because the emotions aren’t getting in the way.

What I fear is that in your increasing desire to hold on to him that you will try to trap him with sex, and it won’t work. You paint a picture of a guy who would not turn down an opportunity but won’t see something freely given as binding in any way. Saddest of all is that you don’t love him as he is; you love pieces of him and what you’ve imagined to fill in the gaps once you “fix” him. Because it is mostly imaginary love (infatuation), it keeps cracking whenever reality rudely intrudes. “Love never fails” (I Corinthians 13:8) is an indication of true love. It grows stronger over time. This isn’t true love. And any attempt on your part to make it true love will fail. “I charge you, O daughters of Jerusalem, by the gazelles or by the does of the field, do not stir up nor awaken love until it pleases” (Song of Solomon 2:7). True love, when it does happen, will grow and flourish on its own. It will come to you. But when you try to rush things or force it, it will run off like a frightened gazelle.


How do you react in a situation where you’re faced with something you think you need, but you know is not good for you? I’m friends with the same people that the boy I wrote about previously is friends with. We’re at events together often since I don’t want to miss out on the event trying to avoid him. At the same time, I feel like my motives might be slanted. Sometimes the thought comes to me that I really go to these events just to see him; however, I want to learn to cope with situations that tug at my emotions. I guess the “bad” side of me wants to go just to see him and be seen by him, to have all of these awkward moments. The sensible side of me knows that it’s hard for me to go places I know he will be. There is also a place in me that just wants to hang out with my friends. How do you distinguish the feeling of doing something with the wrong intentions and doing something with the right intentions when you might lie to yourself to suit your “want” at the moment. How do you at least learn to be comfortable in situations that you feel unsure in?


It comes down to if you are willing to be true to yourself. Would you go to these events or hang out with these friends knowing for sure that he would not be there. If the answer is “yes,” then go ahead and go. You know you are not doing it because he is there. When you make arrangements, make it a point not to find out if he is going or not.

If you find yourself saying “no” because you heard he wasn’t going to be there, then you need to re-evaluate why you are going in the first place.

I suspect that you enjoy the awkward moments because it is a small way of getting back at him, which is not the proper thing for a Christian to do. “Repay no one evil for evil. Have regard for good things in the sight of all men. If it is possible, as much as depends on you, live peaceably with all men. Beloved, do not avenge yourselves, but rather give place to wrath; for it is written, “Vengeance is Mine, I will repay,” says the Lord” (Romans 12:17-19). Or, you think that his squirming means he still has feelings for you. Either way, it isn’t a healthy attitude.