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I’m in love with my friend who still loves his ex – how long should I wait for him?

Ask Roe: I keep hoping he will feel differently and I can’t move on with my life

Dear Roe, 

I’m in love with this guy for three years, and we have been friends on and off. We are really good friends now, but my emotions are only stronger and he has the love of his life. It is his ex-girlfriend who wants to be just friends with him.

I have tried before to cut him out my life, but I think it hurt more when he was not in my life at all. I want to get over him, I want to fall in love with someone else if I can’t be with him, but I think my problem is that I don’t genuinely want it. It feels so real, like I won’t feel this way again, and I keep hoping he will feel different towards me in the future.

My question is, how do I stop hoping? Is it dangerous to hope if it will keep me going, if it will help me do good stuff for myself? I am afraid I will end up alone and be in love with him for years.


The deep irony is that you and this man do indeed appear to have a lot in common. You are both bad at respecting your own emotions, bad at setting boundaries, bad at showing up for something real instead of obsessing over a fantasy.

I know, so many assumptions from such a short letter! But I can tell all of this because he’s trying to be friends with an ex that he is still in love with, and you’re trying to be friends with this man who you are in love with.

If either you or this man respected emotion, didn't loathe your own vulnerability, you would be able to acknowledge and account for your emotions

There’s a very irritating, righteous myth that is gaining traction in the modern dating world, that if you are mature enough or enlightened enough, you should be immediately able to be friends with a person you were recently or are currently in love with, without taking any time apart or ever expressing any conflicted feelings or emotional messiness. It’s nonsense that equates emotional disconnect with emotional sophistication, that derides vulnerability or complexity.

There is a lie at the core of this philosophy, that emotions are inherently negative and civilised people should simply overcome them. Emotions are natural and inevitable, and real maturity, empathy and respect involves acknowledging and accounting for them, in all their glorious, absurd, sometimes illogical unkemptness.

If either you or this man respected emotion, didn’t loathe your own vulnerability, you would be able to acknowledge and account for your emotions. You would be able to say “I have intense feelings for you and they’re disrupting my happiness, so I need to step away so that I can heal.” You would be able to set boundaries.

But there’s a reason that neither of you are doing that. Because it’s easier for both of you to long for someone who doesn’t want you than to show up for someone who could. It’s easier for both of you to love the idea of someone instead of a real person; easier to pine poetically for an impossible love instead of embracing it in the flesh. You both believe that a person who does not want you is the love of your life, without taking the time to think about what that reveals about your idea of love and what you deserve. You are both imbuing someone with the power to define your worth and your life’s experience of love, while ignoring the fact that they do not want this power.

I could go on about your similarities – however, I think you’ve already linked your being and fate to this man long enough, so let’s not continue to do that and instead solely focus on you.

You’ve written a very limiting story about yourself that you need to start unlearning. You’ve written a story in which someone else is the answer to all your deepest desires, the key to your best self, the only good thing about you.

I’m intrigued when you say that your longing for him and hope that you will one day be together helps you “do good stuff for myself”. What does that good stuff entail? And why does he have to be in the equation for you to do them? You could do them yourself, for you, simply because you deserve good things. But I don’t think you understand or believe that. I don’t think you believe you deserve much at all, which is why you keep waiting for a man who doesn’t want you, denying yourself the opportunity to find someone who does.

That’s why even when you do something good for yourself like drawing a boundary and reducing your contact with him, you don’t do it so that you can heal and feel better. You do it for him. You do to see if he’ll beg you to come back. And when he doesn’t, you go back anyway.

Tell him you love him, or set a boundary and let yourself grieve, heal, and move on

You ask how do you stop hoping. That’s not the right question, because you don’t actually have a lot of hope. You have the hope of someone who wants to catch a horizon, and refuses to acknowledge that the horizon is an imaginary line that recedes as you approach it.

That’s not hope, it’s a self-destructive fantasy. It’s a fantasy that will leave you always chasing, always empty-handed. You have committed to someone who doesn’t want you, so that you don’t have to go out into the world and try connecting with someone else who does, because that would require honesty, emotion, vulnerability – and actual hope. And that’s scarier to you than waiting for someone who doesn’t love you. Because waiting is passive. Trying, hoping, is active. And you’re too scared to act. Too scared to embrace your own power.

You need actual hope, and trust. You need to have the hope and trust of somebody who believes that the world is so much greater and more beautiful than one single person; that you are worthy of love and will find it beyond him; that you are enough.

Do one of two things. Tell him you love him, or set a boundary and let yourself grieve, heal and move on. Both options will require you to embrace your emotions, your vulnerability, your desires – and they will require you to act. To face the possibility of being rejected by him or truly loved by him. Either outcome will require you to act also – to move in the direction of something real, with or without him. Do it.

Horizons are beautiful. Admire them from a distance. But know that you deserve to reach out for something, someone, that can reach back.