02-07-2025
Help Me Hera: I think I need to break up with my best friend
A long time ago we almost hooked up. Why am I still so hurt?
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Dear Hera,
I think I need to break up with my best friend. It's a long story.
Some time ago we almost got together. I made myself decline her advances since we were colleagues and I was fresh out of a longterm relationship. A few weeks later we had become even more situationship than friendship, and I decided fuck it, this is worth the risk. I told her I felt the same, only to get turned down. It was awful and we stopped speaking for months.
But time heals! We slowly started spending time together again and now we're closer than ever. She's my best friend. It helped that we both moved on and started seeing other people. We could go back to being mates without any pesky romantic feelings ever getting in the way.
Recently, she brought up the aforementioned mess, and it was a really good chat. We laughed a lot. But one thing came up that hurt. It turns out that the death blow for our 'will-they-won't-they' had been that she'd slept with someone else – a friend – and didn't want to have to tell me. I had suspected this at the time, and it's well in the past, so I brushed it off. I was mostly just happy to finally clear the air on that particularly messy chapter.
Turns out, knowing and suspecting are different things and now I don't know what to do. She is one of my favourite people in the world. People do stupid things. She admitted she fucked up. And this is all a long time ago. We're both happily seeing other people now.
On the other hand though, I don't think I'd have entertained becoming mates again if I'd known for certain. And now I know that I should not have given her the benefit of the doubt.
But I did, and she is now my best friend in the world. Losing her would turn my life upside down. Is it worth doing that over some ancient hurt feelings?
Dear Heartbroken,
I have read this letter backwards and forwards. I have soaked it in lemon juice and held it up to candlelight. I have run it through all known cryptogram cyphers. But I'm struggling to see the justice of your complaint.
There are a lot of mixed messages in your letter. You say you love this friend, and she's your favourite person in the world. That losing her would turn your life upside down. You insist that you're just good friends, and have both moved on romantically. You've laughed about this situation together and become even closer. And then you go and sign the letter 'heartbroken.'
What confuses me most is your anger. Maybe I have Tux Tasty Bites Dry Beef Dog Food for brains, but I have scrutinised this letter from every angle and I honestly can't see what she did wrong. You say she 'fucked up' and 'people do stupid things' and you should never have given her the benefit of the doubt. But what did she do that was so fucked up and stupid? Was it sleeping with someone else, after she'd already propositioned you and been rejected? Was it not telling you that she'd slept with someone else after you'd already changed your mind?
I don't blame you for feeling sad about the situation. I don't even think you did the wrong thing. Jumping straight out of a long-term relationship into a new romantic fling with a close friend and coworker is a high-risk situation, and I can completely understand your initial trepidation. The fact that your feelings eventually won out, only to discover you were too late, is obviously painful. Missed opportunities hurt more than outright rejections.
What isn't fair is blaming her for this mess. It's not pleasant to discover someone you have a crush on has slept with a friend. But even if there was still some simmering romantic tension between you, or you'd started sleeping together casually, it's not fair to expect her to keep a respectful period of monogamous celibacy on the off chance you'd change your mind. You're processing this like a romantic infidelity, but you can't cheat on someone you're not in a relationship with, especially if you've already made it clear to the other person that a relationship isn't on the cards. While the situation is undeniably messy, even if your friend regrets her choices, it doesn't mean she 'fucked up.' Perhaps your hurt has to do with the conviction that if she hadn't slept with that friend, things would have turned out differently between you. It's fine to be mildly tormented by regret. But you share some responsibility for the way things unfolded between you.
Maybe you'd say that your hurt isn't to do with the fact that she'd slept with someone else, it's that she didn't tell you. But then you go on to say that if she had told you, you'd never have entertained becoming friends again. This makes no sense. If you want to opt out of a relationship because the rejection is too painful, that's one thing. But you can't have your cake and fuck it too.
Did she have an obligation to tell you? Considering you were already hurt enough to stop talking for months, I can't see how her offering up this information would have been relevant or productive at the time. You can't expect full transparency from someone you're not on speaking terms with.
I think the reason you're having a hard time reconciling this perceived 'betrayal' with your current platonic friendship is because you still have residual feelings for her. You say that these days, you're strictly platonic. But this whole letter is bogged down with retrospective anguish. I think part of you must still be holding a candle for this girl, or the situation wouldn't hurt so bad.
Perhaps there's some specific emotional nuance I've missed in your letter which is fuelling your sense of retrospective injustice. But from where I'm sitting, it looks like you're struggling to forgive someone who doesn't need your forgiveness. I'd encourage you to do a little soul searching and be honest with yourself about why you're so hurt. If you can't move past this, perhaps your feelings aren't as platonic as you think, and you're not ready to be friends. There's no shame in that. But don't act like the wounded party. Sometimes there's nobody to blame.
