How to Break Up With Someone

Should You Break Up or Work It Out?

Sometimes it’s easy to know when to dump someone. If you’re getting treated like shit, being constantly ignored, cheated on, or experiencing any other combination of toxic relationship shit-baggery, you need to leave. Skip this section and go straight to the steps below. Now.

But many times, breaking up is not such a clear-cut decision. Maybe things just aren’t clicking. Maybe the arguments don’t seem to be going anywhere. Maybe you’ve run into some compatibility issues that aren’t terrible, but you’re not sure you can live with. I get it.

If this is the case, it’s worth digging a little deeper to find out what’s really going on here. Because in intimate relationships, any problems we’re having are rarely what they appear to be on the surface. That is, it’s never really “about what it’s about.”

I’ve written much more extensively on deciding whether or not you should break up in the first place:

When to Break Up with Someone—And When to Stick It Out

But I’ll summarize briefly here:

• Identify the real problem in the relationship.

  Again, it’s never really about what it’s about. Why are you filled with rage every time they leave a dirty dish on the coffee table? I can tell you right now it’s not about the dirty dish. Maybe your ideas of cleanliness are actually a deep-seated desire to control your environment because you can’t handle the anxiety of all the uncertainty in your life. Dig a little deeper and see if you can find a little compassion for the other person—and yourself while you’re at it.

• Have you communicated that you’re not happy?

  I’m surprised by the number of people who say they were blindsided by a breakup. Relationships don’t just dissolve in a single moment. It takes at least a little time for things to fall apart. So once you’re feeling like things are getting a little off track, you owe it to the other person to give them a chance to make things right.

• Can you live with a compromise?

  We’ll never be perfectly compatible with another person in every way imaginable. But there’s a difference between having different preferences—like not liking the same foods—and having different values—like whether you want kids or not, how your spend your money, religion, etc. It’s ok to compromise on your preferences from time to time. It’s not okay to compromise on your values.

• Enforce your boundaries.

  If you’ve done all of the above and the other person is fully aware of where you stand, then it’s time to enforce your boundaries. And that means demonstrating a willingness to leave if things don’t change. If you’ve given it a good faith effort and someone really wants to make things work with you, they’ll also make a good faith effort to help change the relationship. If they don’t, it’s probably time to leave.

Unf*ck Your Relationships

Dump the toxic relationship cycle with my free mini course on attachment styles.

Get Ebook

Your information is protected and I never spam, ever. You can view my privacy policy here.

10 Rules for Breaking Up Gracefully

So this is probably going to suck. But if you’ve decided it’s time to pack it up and shut down the relationship, well, I commend you on your bravery.

Now let’s get through this fucker.

1. Always Do It in Person and If Possible, Don’t Do It in Public

Unless they did something totally out of line like scalp your cat (or leave you 43 tearful voicemails in one night), and if you have any respect for them at all (often a legitimate question), then always do it in person.

Yeah, it’s harder. But suck it up. And if possible, don’t do it in public. Being in public makes people feel limited in what they can express, whether it be final words they’d like to say to you, or dishes they’d like to break. Which brings us to principle number two…

2. Never Make a Scene and Keep Your Batshit to a Minimum

Feeling distraught is OK. Being torn apart from the inside out is fine and expected. Wishing fiery hell and brimstone onto your ex and feeling the urge to dismantle their life and everything they hold dear piece-by-piece… isn’t totally out of the ordinary either. But any attempt to do so is going to just make you look like a child throwing a tantrum. Control yourself. Grieve and express your pain, but don’t do anything stupid. Do it in private and do it with someone you trust.

And this goes double if you’re in public. Here’s a good example how not to deal with a bad break up, as demonstrated by a Brazilian woman here in São Paulo:

3. Do NOT Try to Make the Other Person Feel Better

This goes particularly for the dumper (cue Beavis and Butthead laugh). Once the relationship is severed, the other person’s emotions are no longer your responsibility. And not only is it no longer your responsibility to help them cope, but comforting them will likely make them feel worse. It can also backfire in that it will just make them resent you more for being so nice (while dumping them).

And for fuck’s sake, don’t have sex with them. Seriously, you just broke up. They’re crying and saying how much they’re going to miss you. You hug them to make them feel better. You start getting upset because you wish things could have worked, but this is for the better. Suddenly you’re tearing up and wondering why you’re dumping them in the first place, because god, remember when things were good? They were great, right? Then the clothes are off and one of you is crying and smiling and suddenly the sex is more passionate than it’s been in a year and a half and what the fuck, what are you doing? No, really, what are you doing!? Stop!

4. After the Breakup, Respectfully Cut All Contact for a Short Period of Time

This is the second thing that many people don’t muster the courage to do. A lot of people get hung up on remaining friends and actually force contact when it’s causing them more emotional stress.

Research on relationship breakups finds that people who limit contact with one another emotionally recover much faster.¹

Not only is it totally reasonable to refrain from seeing/speaking to each other for a brief period of time, but it’s healthy. The more contact you have, the more you run the risk of setting off an emotional time bomb, relapsing, and ending up in that messy no-man’s land of “we’re not together, but we’re still kind of together, but we’re definitely not boyfriend and girlfriend. I’m going to call really quick to check in, but seriously we’re not together — why are you looking at me like that?”

5. Talk to Somebody About It

This one may seem obvious, but make sure you do it. If this is a particularly serious relationship, talk to a trusted friend or family member before making the decision. And then take whatever advice they give you seriously. We are often poor observers of our own relationships, but our friends can see how it’s affecting us better than we can.

6. Allow Yourself to Be Sad/Angry/Upset but Don’t Judge or Blame Anyone

Emotions are healthy and normal. Even negative emotions are healthy and normal. But judging and blaming people, whether it’s them or you, doesn’t get you very far.

This doesn’t mean you shouldn’t distinguish good/bad behavior or good/bad choices. Learning from your errors and what went wrong in your relationship will go a long way to helping you move on. I was really messed up about my first serious relationship. I harbored a lot of resentment because she left me for another guy. I didn’t really start to get over it until I came to terms with all of the ways I wasn’t that great of a boyfriend. Once I realized that I wasn’t such a perfect angel and that I wasn’t completely the victim, then it was easier to come to terms with what happened and let go of them.

Start by recognizing that maybe they weren’t as great as you thought and there really were some things you didn’t like. Recognize the things you didn’t do well and how you could have been a better partner. But don’t blame them or trash them as people. Everyone goes into a relationship with the best of intentions. Most people come out of them feeling hurt and betrayed in some way. Most people come out having messed up royally somewhere along the way. There’s nothing uniquely horrible about you or that one person. Just learn from the mistakes and move on.

7. Recognize That the Break Up Itself Is a Sign of Your Incompatibility and You’re Both Better Off

Here’s something that grates on me: people who just got out of a relationship and lament that “he/she and I were perfect together.”

Obviously you weren’t. Otherwise, you’d still be together.

For some reason when it comes to judging someone’s compatibility, people suddenly excise out the fact that they aren’t together anymore. Oh yeah, even though we were clawing at each other’s throats for the last six months, that first trip we took to Florida was magical. We were just so right together.

While we do all have perceptual biases for remembering things better than they were^{2, 3}, it’s important to remind oneself that you broke up for a reason. And often that reason is a very good reason.

And for those of you still holding onto that one special someone months or years later: stop. If they were right for you, they would have realized it by now. You’re deluding yourself. Move on.

8. Invest in Yourself

The longer you spend in a romantic relationship, the more your sense of identity melds with theirs. Being together with someone in such an intimate space for so long creates a third, overlapping psychological entity that comprises both you and them.

And when that entity suddenly dies, not only is it painful, but it leaves a temporary void in who you are.⁴

This is why the best and most important post-breakup advice on the planet is to invest in rebuilding your personal identity. Rediscover your old hobbies. Focus double on work. Start that new project you’ve been putting off for months. And most of all, spend time with your friends. Your friends will not only reassure you and make you feel better in the moment, but they will also help you reinforce your own personal identity again. Friendship is the best medicine for heartbreak.

9. Only Start Dating Again When You’re Legitimately Excited to See New People

A lot of people break up and enter a “rebound” period. They’re immediately back on the market and throwing themselves at the first thing that comes by. The problem is this is more of a coping mechanism than genuine enthusiasm for the new people one’s meeting. You can tell because the new connections you make feel complicated and lacking. Anxiety and desperation come back with a vengeance, and overall the process of meeting someone new is far less enjoyable.

After you break contact and invest in yourself, don’t pressure yourself to meet someone new until you’re legitimately excited to do it. There’s a difference between excitement and desperation. Desperation is feeling alone and incomplete without dating someone — like you need to be with someone to be happy. Excitement is being genuinely excited to discover what’s out there and feeling fine regardless of what happens.

Besides, when you’re excited to meet new people and are in a good place emotionally, you are far more attractive anyway. It’s worth it.

10. Only Attempt to Be Friends With Your Ex Again Once You’re Over the Idea of Dating Them

Some people have the admirable goal of remaining friends with their ex. Other people have the admirable goal of breaking the kneecaps of their ex with a tire iron.

Whatever the goal for your future relations with your ex, they need to happen organically. Forcing a friendship enters into testy territory as it can make the other person feel obligated to you and that can kick up a lot of the negative feelings leftover from the break up.

What I’ve found is that if you had a strong friendship within the relationship, that friendship will naturally emerge outside of the relationship once you’ve both moved on. In a lot of cases, it takes dating new people for both parties to relax enough to form that bond again. Other times it takes a lot of time. But if that friendship is there, it’ll eventually sprout up. Do it a favor and don’t force it.

Is Trying to Get Back Together Really That Hopeless?

I often get emails from people with their break up situation asking if it’s hopeless. Is there any chance they may end up back together?

Here’s the deal: if you get back together after one break up, it can work. But that’s assuming that one or both of you genuinely learns from the break up and alters the course of their behavior or their perception of the relationship. There are plenty of examples of couples who needed some time apart to gain perspective on the relationship and learn how to make it work. And generally, only one catastrophic break up isn’t too much to heal.

But if you’re going through break up after break up after break up — or what I sometimes refer to as the “emotional boom/bust cycle” — where you’re either in bliss or in hell, depending on which month it is, then I hate to say it, but you should probably just end it permanently.

Imagine your relationship as a beautiful china plate. If you break it once, you can put it back together with some care and effort. If you break it a second time, you can still put it back together but it takes a lot of extra time and care. But if you break it again and again and again, eventually you end up with so many pieces that you can’t put it back together. And no matter how much you liked that plate, you’re better off going and finding another one.