Dear Dana: How Can I Break Up With My Boyfriend Without Crushing Him?

Dear Dana is a bi-weekly advice column for humans who engage in romantic relationships. Please send your dilemmas, issues, conundrums, assumptions, conflicts, anxieties, worriments, obstacles, complications, predicaments, queries, questions, and any other synonyms for “problems” to

Dear Dana, 

I’m in college and I’ve been dating my boyfriend for two years. He and I are really good friends and everyone who knows us assumes that we’re going to be married, but I want to break up with him.

I love him, he’s a dear friend, but I don’t want to spend the rest of my life with him. I’m too young. I was planning on breaking up with him before the holidays but I chickened out because it seemed mean to make him spend Christmas newly dumped. But I need to dump him.

I’ve told all of my friends that I’m going to break up with him so now I have to do it. But I still haven’t done it. He tells me all of the time that I’m the best thing that ever happened to him and I don’t want to crush him.


Desperate to Leave


Dear Desperate to Leave,

Which is worse: to dump someone or to get dumped? I’ve been dumped tons of times, to the point that I had a system in place. After the painful conversation in which it was made clear that my presence was no longer needed, I would immediately: call my sister, call my mom, call all of my out-of-state friends, call all of my in-state friends and make plans to get drunk together in the near future. I would go to CVS and purchase ice cream, cookie dough, nail polish, fashion magazines, and other clichés in hopes that they would make me feel better. I would take all these things home and do my nails and eat ice cream and feel bad. I would watch TV and quietly cry while pretending that I wasn’t. I would wonder what I had done wrong. I would be ashamed.

There are many pop songs devoted to the plight of the dumpee and few devoted to the cause of the person who wants to leave. I think that’s because we presume that leaving is easy and being left is hard. But I’ve found that the opposite is true: those who are dumped have so many recourses for sympathy and healing and ice cream, while those who do the dumping are assumed to jet to Paris immediately afterward to start torrid love affairs with attractive people in tight pants.

A few years ago I found myself in a long-term relationship that had run its course. I was miserable and, once I realized that he was miserable, too, I summoned the courage to end our relationship. It was the right decision, it was a good decision, it was a decision that enabled both him and me to find new love. But it was also the hardest thing I have ever done.

I wasn’t prepared for the fallout. I wasn’t prepared for the part where I apologized to him, and his family, and our mutual friends, over and over again. I wasn’t prepared to be so overcome with grief that I didn’t eat for days. I spent weeks either numb or crying. I felt as though my life had ended.

I was devastated and the hardest part was that I had perpetrated the devastation. I had hurt him, but I had also hurt myself. When you dump someone after years of dating you set fire to your own life.

To plan to break up with someone is to live with the slow, sick dread of what you must do. Telling someone you love that your relationship is over is so difficult because you love him, you do, you want him to be happy, you do, but you know something he doesn’t: Your time together has already ended. The official break up is, in many ways, a formality.

You state that this man calls you the best thing in his life. You need to know that he is wholly incorrect. Because you’re actually the worst thing in his life. You are a straw man, a red herring, a false god. You are standing between him and the glorious realization that he is the best thing in his life.

This is a desperately important piece of information that we all (hopefully) get to eventually, but in the meantime you are actually preventing this man’s future happiness. You aren’t helping him out by half-heartedly dating him while asking everyone else to help you escape. He deserves to be with someone who wants him, all of him, forever and ever.

That person isn’t you and it is therefore your obligation to get the fuck out of the way.

Real talk: When you start dating someone, you’re basically agreeing to let the other person break your heart. Sometimes that heartbreak is the result of a break up, but sometimes it’s the result of learning that the person you love is entirely flawed, fallible, and unlikely to change. And then you either leave them in pursuit of the next potentially perfect (yet inevitably imperfect) partner or you forgive them, and yourself, and you tuck in to explore the flaws together.

But you don’t want to do this. You don’t want to explore his flaws. You want to get out. You want to dig a hole in the wall and disappear, Andy Dufresne –style. You want to tunnel out in the dead of night through the sewer system and somehow appear on the other side, free for the first time in years, but you also want achieve this without smelling like shit. This desire is understandable and completely unreasonable.

There is no way to break someone’s heart and come out a hero.

It takes two people to date. The desperate need of one person should not sustain a relationship. If you no longer wish to be with this man, then you should no longer be with him. You don’t owe him your affection. Putting off this hurt is only making the eventual, inevitable hurt that much worse. He’s going to figure out that you’ve been wanting to do this for a while. He’s going to dislike you. He’s going to be hurt and then angry and then hurt again. He may use your break up as an excuse to make bad decisions. But that’s OK. Because you aren’t the best thing in his life, you aren’t the only piece holding it all together for him. You’re just one person who wants to be somewhere else. You have to hurt him, and yourself, so one day in the future you, and he, can be better.

So go. Stand in front of him and give him a clear, honest, and direct break up. And then leave. Walk away. And know that one day it will be a year from now, you will be free, and he will be much, much happier.

Dana Norris once went on 71 internet dates, many of which you may read about here. She is the founder of Story Club and editor-in-chief of Story Club Magazine. She has been featured in McSweeney’s, Role Reboot, The Rumpus, and Tampa Review and she teaches at StoryStudio Chicago. You may find her on Twitter at @dananorris. 

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