How to Break Up with a Girl (From a Guy Who’s Done it Wrong a Few Times)


Mark Radcliffe would like to spare fellow guys the mistakes he’s made in the break-up ritual.

One of the most difficult ordeals a guy can face is the delicate matter of ending a relationship that his girlfriend still wants to continue, especially if he still cares for her. There are some good ways to go about it, but infinitely more bad ones, and I’ve certainly plumbed the latter category more times than I’d like to admit over the years. So in there interests of sparing men (and women) the mistakes I’ve made, here’s what I’ve learned from my past:

First, before we can even get on to the delicate matter of how to break up with a girl, there’s the more important question of should you: Is it actually necessary? Are the reasons you think you need to break up legit? Are they instead things that can actually be worked out? Improved in some way through rational and honest conversation?

If you are certain they are not, very well then, let’s proceed:

First off, you had better make sure you’ve earned the right to break up with her.

Earned?” you ask?

Yes, earned. If you haven’t already had a number of conversations about your misgivings about the relationship, then you’ve got a few steps to go through first.

Because the one thing that will make you an outright asshole is if she’s hearing about these complaints for the first time. Employers can’t fire you without a few warnings first, and the same applies in relationships: you need to establish a pattern here. If you’re too much of a coward to have those tough conversations first and let her respond to what you’re unhappy about (and even let her yell a bit), or are too lazy to work together to change things, then you’re not ready to break up yet. And you’re probably also not ready to be in a relationship yet, either. (And yes, I’ve beenboth of these guys over the years.) But the point is, you might learn through these conversations that you’re a bigger part of the problem than you realized, and some of the onus of fixing it is on you.

Exemption clause: of course, if you walk in one night and catch her sleeping with your best friend, then sure, no real discourse is needed, you’re fully entitled to hit the eject button. (Or if she accidentally burned your vinyl record collection—I mean, we all have our limits.) But otherwise, if everyone broke up with each other at the first infraction, the human race would never get around to actually reproducing.

Second: Is it a good time for a breakup? Can she handle this right now? If you really care about ending it tactfully, and not causing her immense pain and getting anointed as public enemy number one, perhaps you can wait another week until she’s through passing her med school boards, or till after her sister’s wedding, or till after she’s had that appendectomy. That said, if ‘waiting till it’s a good time’ results in putting it off a year, at some point the trigger just needs to be pulled. There’s never a ‘great’ time for a breakup, just try not to pick the worst.

Third: you’re going to be the asshole no matter what. It will vary in degree, but there’s usually no way you’re going to walk out of this with her giving you an enthusiastic high-five. Be prepared to be the recipient of her fury/ resentment/ or depression. It’s your unique door prize to inherit for playing the role of dumpeur. Man up, and be ready to take the heat. Your reasons may be sound, and in time, when she finally meets the guy she’s eventually going to marry in six months’ time, you’ll be forgiven a bit. But not now.

Forth: try to pick a good place. The important elements are: privacy, a calm environment, a quietenvironment, and preferably a place where she can have a bit of a breakdown if the moment requires. It may sound cruel on the surface, but I personally recommend doing it at her place, where most of these elements are in place. That way, you can leave once the conversation seems truly ‘over,’ and she can have the comfort of her own environment to fall apart in. If you do it atyour place, then she has the additional hurdle of trying to get herself home. While crying. In downtown traffic. As your favorite U2 song comes on the radio. If it has to be a public place for some reason, don’t pick a restaurant or café or anywhere else where you’re in full public view. Look for a park, or somewhere with a bench away from a crowd.

Fifth: we’ve all probably heard this before, but “I statements” not “you statements” are key here, and are essential if you don’t want the whole thing to turn into an emotional volcano. Say “I feel like I’m not being heard,” not “you never listen to me.” “I feel I can’t be myself around you” rather than “you’re too controlling.” And if it seems that it’s not really working for her either, point that out, so it’s not just about your needs, it’s also about what’s best for her future, too.

Sixth: honesty is important, but only up to a point. There is a point where you can go too far and do irreparable damage. Of course, there’s no point in completely sugarcoating it either, or else she’ll be left in the dark as to why you’re leaving. You can’t just tell her “I just want something new” if the truth is more like “I don’t feel like you support my dreams and aspirations.” There are a few exceptions, I think, such as if you’re not really attracted to her (in which case you’re a jerk, since: what were you doing dating her in the first place?), or is if the sex is lousy. Telling a woman she’s bad in bed (and again, the problem might not be her, it might be your inability to communicate what you like, or that you have different approaches to sex) is about the sharpest knife you can plunge into her heart. She might never recover her confidence from it. “We don’t seem sexually compatible” is about as far as you can go with this one, but if you can focus it on the conflict in values and lifestyles, that’s easier to swallow.

Seventh: give her some indication it’s coming. Don’t blindside her when she thinks you’re just going out to see a movie. I made this awful mistake once, thinking it would be easier, and have regretted it every since. It might be easier for you to stay in lala land before you drop the bomb, but it’s cruel to her. Tell her “I think we need to have a talk” at the very least.

Finally—if you can—tell her you’re open to talking about it some more if she wants to (and if you’re able to handle it). And then walk away. At some point, the breakup talk needs an endpoint, so she can process. And be aware that, just because the talk is over, doesn’t mean the process is over. There will be followup waves. And if you’re truly trying to be a standup guy, you’ll stomach a few of them. Give her the answers she needs, if she wants them, and you can provide them. But at some point, you’ll inevitably need to just cut the cord, at least for a while.

And since we can’t always plan our breakup talks—sometimes they just happen—at least try to handle them with dignity. Rather than place blame, explain how the relationship just isn’t giving you what you need—spiritually, conversationally, romantically, financially, whatever. And remember that even if your time with this woman has come to an end, her romantic life hasn’t, and there will be other relationships that she can apply these learnings to. No matter how unhappy you may be with your relationship, don’t let her sour on love or men altogether. We men all have to realize: right now there’s a guy out there breaking up with a woman we’ll one day date ourselves (or even marry). And just as we don’t want him burning her so hard she puts up a wall we can never get through, let’s all try to do the same for him. Pay it forward by ending things gracefully, so she can love openly again, and hope that the guy who might be dumping your future wife has the maturity to do the same.

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About Mark Radcliffe

Mark Radcliffe is a writer living in New York City. He has a weakness for bourbon, jazz and girls who can drive stick. You can read more of his essays here: and


  1. Just had to share a recent ending of my own. I don’t believe breakup etiquette is restricted to older men. I recently met and dated a man of 44. We spent time in my space and it was amazing. He then invited me to visit him, he lives in another country, and I did. The minute I got of the plane he switched and lost interest in me. Was it because he felt overwhelmed with me in his space or was I just the woman he didn’t want in his space? Be that as it may I was supposed to stay for a month but left after 3 weeks. In retrospect I should of left even earlier than that. It was strange that when he was with me in my space he treated me beautifully but as soon as I got to his space he switched. I have no idea why. In trying to figure things out after I returned home I had a conversation with a girlfriend and between the two of us the only logical explanation we could come up with was that my feet must obviously stink! :) I don’t think any of my ex’s has ever told me why they broke up with me or why they switched from being so in love to being so out of love. I wish that I had been given some straight answers so that I could then learn from them.

  2. This is a great article. As a woman who’s gotten dumped by several men in really awful ways, I would add:

    1. If it’s a long distance relationship, break up by phone. Don’t make your partner go to the effort of traveling to see you, only to get dumped. And then having to suffer the awkwardness of spending the weekend with you after you’ve dumped her. Been there, done that.

    2. Don’t just disappear. Have the balls to be honest and say you want to break up. I’ve been in a position of having to inquire whether a person was still alive, because he just stopped all communication, with no explanation or warning. It was pretty surreal.

    3. Be honest. We can take it. Don’t “spare our feelings” by not saying you want to break up. Allow us the dignity to grieve and move on, not get mixed messages and waste another 6 months in a bad relationship. Women are much stronger than a lot of men think we are.

    • Yup #2 is a definite no-no, I’ve had that happen 3 times in the last few years. Guys be honest – don’t just bail without any explanation at all, apart from anything it makes the female feel like an idiot when she thinks because the last time you spoke it was all unicorns and rainbows that you’ve been in an accident or died – only to find out you just couldn’t be arsed to be honest.

    • In my experience, most guys are cowards who do a disappearing approach. Males from 22 – 60. Spineless boys.

    • Oh, #2! SOOO #2!! I was going to add it myself, but you’ve covered it.

      I have been in the same situation – literally, had someone disappear so suddenly and so strangely that I too honestly found myself wondering if they might be dead, and if I should contact the police … never did hear from him again, so I don’t know, maybe he was!? … eek …

    • #3 – Yes. We are resilient creatures. If not, that is our problem to work on, not yours to avoid.

  3. Actually, it seems the most common “break up” method these days is to just disappear.

    Any advice for what to do about this, or how to react to it, GMP?

    • I’d like to hear some advice too … I don’t know, as I get older, I find myself less inclines to do the dignified-walk-away-silence, and more inclined to step up, call them out on it, make them accountable for their actions and MAKE them confront heir decision …. not sure I could pull this off as successfully in real life as I do in my imagination though!! 😉

  4. Dina Strange says:

    Most importantly don’t be a coward about breaking up. Don’t do it by email or text message or in the middle of a fight. Also, when breaking up admit your mistakes – don’t blame a girl for your own mistakes. It makes you look pathetic and weak. And finally communication. Explain why it’s not working out for you and be honest. Same goes to women too, btw.

    • Some men are bigger cowards than they like to admit. My ex recently broke up with me with a message on Facebook, of all places.

  5. keli138 says:

    This was a very mature topic and beautifully written. Thank you for adding this to the tool belt of the readers. Many men and women will benefit, on both sides.

  6. Baigu Akloa says:

    Why break up? Just stay together and work it through.

  7. Thanks for this article. From experience, I definitely winced when I read the “is it a good time for the breakup?” I had an ex use this as an excuse when we did in finally break up… Which actually only happened because I’d gotten a phone call from a girl… he’d been dating (while going home to see his kids, mind you)… For 13 months. 13 MONTHS. I know the point in the article was more based on short term issues – wait until after exams, that important meeting etc. and in a way I just want to emphasize that point. But he took it way too far and was a complete coward because we had some talks, prompted by me, and he lied through his teeth about it. (Yes I’m aware of how these issues are his and not mine to claim.)

    Realizing I don’t want to miss the point of my comment with excess detail, my point is simply this: Guys (and gals) : Don’t play god. It’s not up to you to “protect” anyone from heartache. It happens. It’s a cowardly and selfish excuse to procrastinate, while unfairly keeping someone you once cared for (remember that?) in the dark. As stated, there’s never a good time for a breakup. People always have something going on that’ll make it not the right time. But step up and be honest, and start first with yourself. Then have the conversations. Show some respect for this person that you once were so intrigued to explore life with. Things don’t always work out. HINT: This really shouldn’t come as a mind-blowing surprise to anyone. It may be sad or a little unexpected (read: denial), painful and most certainly uncomfortable, but respect is key here and I think this covers that beautifully.

    So yes, thank you.


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