Reading Time: 29 minutes

Of all the difficult conversations in life, the breakup conversation is probably one of the hardest.

But breaking up with a friend — especially a friend you have a long history with — is a uniquely brutal one. Especially when there’s no clear protocol for delivering the news.

At every stage of life, our relationships go through transitions. Some relationships evolve and deepen with time; other relationships stagnate and wither. And all relationships — even good ones — will hit conflict points eventually. If those conflicts are unresolvable, they can spell the end of the relationship — and obligate you to formally “break up” with a friend.

But how can you feel secure in that decision? How do you prepare for that conversation? And how do you deliver the news in a way that achieves your goals without creating even more unnecessary conflict?

That’s what we’ll be talking about in this piece: when, why, and how to part ways with a friend.

But before we dive in, we have to take a huge step back and…

Clarify the conflict.

Before you call it quits with a friend, it’s worth taking a moment to get clear on what the issue between you and this person actually is, and whether you can resolve it.

Sometimes our impulse is to end a friendship as soon as things get rocky, when we really just need to process the conflict and talk things out. This is partly a function of our culture and our programming, which tends to favor conflict avoidance over healthy conflict resolution — even if it means losing out on more years of a great friendship.

So before you fire off that “we need to talk” text…

Get clear on the problem at hand.

Start by asking yourself a few basic questions.

What is the crux of the conflict between you and this friend?

When did this issue come to a head?

What other issues or concerns is this latest conflict bringing up?

Is the conflict about one specific event, or is it part of a larger set of issues?

Why is this conflict impacting you so much?

Is the specific grievance activating some deeper concern, belief, or vulnerability on your part?

Are your expectations for this friend reasonable? Is your friend operating under the same set of assumptions about what your relationship should look like?

And most importantly: Is this problem theoretically fixable if both of you are open to talking?

I get a ton of letters from people every week asking for advice about friendships that have gone south. They’re fed up with their buddy’s attitude, they’ll say. They’re frustrated by a lack of reciprocity from their neighbor. They’re angry about that embarrassing thing their maid of honor blurted out over brunch.

What I find interesting about these stories is how often people can’t pinpoint precisely why they’re fed up. They’re having a more generalized experience of anger, disappointment or hurt — but they’re not able to articulate specifically what about the event affected them so profoundly, or even how those feelings came to be in the first place.

So before you break up with a friend, I would take some time to consider the full anatomy of the conflict at hand. Investigate the injury you feel, parse the pain, and become a student of the situation overall.

Do some journaling if it helps. Write down your thoughts to make them more concrete. Talk the problem out with a couple of trusted friends, and invite them to give you an objective take on the situation.

At this stage, you have to resist the urge to confirm your current interpretation of events and start getting curious about all the sources of the injury you feel.

To do that, make an effort to look at both sides of the equation — the internal and the external sources of your grievance, what you and your friend are each bringing to the problem.

For example, a few external sources of the injury might be a friend’s rude comment, a thoughtless move on their part, or a lack of action.

Meanwhile, the internal sources could include your sensitivity to criticism, your interpretation of the other person’s intent, or your mismatched expectations for the relationship.

If you can hold both sides of this equation in your mind — what your friend has done to you and why that action has affected you so deeply — then you’ll be much better equipped to resolve the conflict at hand. And you’ll probably be more eager to do so, too.

But if you only focus on what the other person has done (or failed to do), then you might prematurely jump to the breakup option. Or you’ll try to talk to your friend about it, but you’ll only be seeking validation, rather than a better understanding of what actually happened — which will only create more problems in the future.

Take ownership of your role in the conflict.

Every dynamic requires two people. Even if a friend is the primary aggressor in a difficult situation, the effect and meaning of that aggression are always co-created by you.

I’ll say that again, because it bears repeating.

What you experience as an injury is a collaboration between you and the other person.

Yes, people can hurt you. Yes, people can let you down. Yes, people can make mistakes and objectively be in the wrong.

But how you respond to and interpret those injuries — that’s all you, baby.

Then you bring that response and that interpretation into your reaction, and the other person reacts to your reaction. And back and forth we go, until the layers of the conflict become so complex that we often lose sight of who’s really at fault. Which is precisely why talking this stuff out is so important.

So get curious about how that conflict is being created. Ask yourself what role you’re playing in it. Look for those actions/reactions. And take ownership of your piece of the puzzle.

Case Study: The Friend Who Isn’t “There” For You

Let’s imagine that you and your friend grab lunch one day. While you hang out, you bring up a difficult conversation you had with your boss, and how it’s affecting your mood these days.

In response, your friend subtly dismisses your version of events and downplays your feelings. It’s not clear if it’s intentional or unintentional, but that’s the effect.

You then get quiet and withdraw, and don’t tell your friend that their response disappointed you.

The next time you grab lunch, your friend tries to talk to you about their difficult colleague, and this time you aren’t very compassionate toward them.

Unlike you, your friend gets angry and calls you out for acting like you don’t care, and you defend yourself. The fight escalates with no resolution, and you don’t speak for a couple of weeks.

You then spend those two weeks feeling let down, misunderstood, and maybe even kind of worthless — which makes you question the value of all of your friendships.

Then you take that mood with you to work, which makes the next exchange with your boss even more difficult, cratering your outlook at work even further.

You feel the impulse to reach out to your friend to talk about it, but you and your friend are on the outs because of the earlier conflict.

Now you feel angry, ashamed, alone, and stuck with all these feelings.

When things calm down a bit, you reach back out to the friend who upset you, and neither of you brings up the fight. You carry on as if nothing happened — which allows you to have contact again, but lets the resentment fester beneath the surface.

Then, the next time your friend says something dismissive or hurtful, your response is even stronger — because the old injury is still alive and your response is exactly the same (and vice versa).

And that pattern continues until you guys either have it out, or you stop spending time together to avoid the argument.

In that brief story, you can see how the action/reaction of each party contributes to a situation that is much bigger than the original grievance.

Your friend fails — intentionally or unintentionally — to be there for you in one conversation, and through a series of responses and interpretations, that rift becomes a crisis.

In this scenario, you’re more or less angry at your friend for not “being there” for you.

But if you dig a little deeper, you might find that your friend’s insensitivity — which was real — was only the beginning of the story.

The rest of the story — probably the bigger part of the story — is what you do with that experience of someone not having your back.

Your friend’s problematic behavior triggers a response in you, which gives rise to a series of negative thoughts and feelings, which creates a larger story, which only perpetuates the negative thoughts and feelings, which contributes to a bigger grievance, which ultimately has very little to do with what your friend initially did.

So while it’s absolutely true that your friend wasn’t fully being there for you in that conversation, it’s also true that you weren’t being there for yourself.

Because if you were being there for yourself, you would have spoken up the moment something didn’t feel right. Or texted your friend later to say that their response bothered you and you would have appreciated a different response. Or found a way to process these feelings and forgive your friend. Or been more careful not to allow those feelings to creep into your work life. Or made it a priority to resolve the issue the next time you saw your friend.

Now, let me be clear. This doesn’t mean that your friend didn’t do anything wrong.

What I am saying is that what you experience as “frustrating” and “disappointing” and “hurtful” is actually a process that takes place between you and the other person.

Which makes the emotional math of who’s “right” and who’s “wrong” in a conflict a little more complicated than it first seems.

Of course, there is some objective truth in any conflict. If a friend insults you for no reason, they’re obviously in the wrong. If they show up 45 minutes late to your baby’s baptism, they’re clearly the a-hole.

I’m not saying there aren’t true facts.

But consider the bigger picture.

Why did your friend feel the impulse to insult you? Is there a shred of truth to what they said, even if it hurt? How did you internalize that comment and incorporate it into your sense of self?

What led them to be late that day? Was that a reflection of how they feel about you, or was it a result of their own chaotic time management? How did you deal with your friend when those problems popped up?

And how did that conversation — or lack of conversation — perpetuate the pattern?

That’s what I mean when I talk about “taking ownership of your role.” It just means acknowledging that the conflict wouldn’t exist if you weren’t bringing something — even a tiny piece of it — to the table. It’s Jocko Willink’s concept of extreme ownership, except applied to your relationships instead of on the battlefield in Fallujah.

Okay, okay, you might be saying. It takes two to tango, I get it. But isn’t this an article about how to break up with a friend? Why are you harping on conflict resolution if I’m just trying to tell my buddy Hank that he acted like a dick and I don’t want to see his dumb face anymore?

For one thing, because you have to be clear about your relationship dynamics if you want to lead with honesty and integrity.

But more importantly, people end friendships over these conflicts every single day, and they don’t even realize how they’re contributing to the situation!

They turn away from a friend when a problem crops up, but what they’re really doing is turning away from the parts of themselves they don’t want to acknowledge.

Which is a real shame. Because then they’re losing out twice.

Keeping Your Side of the Street Clean

If you do this exercise, you might realize that what seemed like an outside injury was actually a self-inflicted one. The source of your negative emotion wasn’t all that painful, but your response to it created the suffering.

Or you might find that the cause of the emotion — the incident in question — was actually just the tip of the iceberg, and what really bothers is something much older, or deeper, or more personal.

Or you might find that you misread the other person’s intention, and created a narrative that didn’t accurately reflect the facts.

Or, as is often the case, that all of these factors were at play.

From there, you have two options.

You can either let the injury go, and feel relieved that you didn’t end a friendship over it.

Or you can be clear about what the other person did to upset you — and then know which piece of that conflict to work out with your friend.

In most cases, these conflicts are absolutely resolvable. Which means the next step is to…

Talk it out.

Once you’re ready to discuss the issue, schedule some time with your friend. Find a semi-private place where you can talk without censoring yourself or causing a scene. (I’m a fan of having these chats at someone’s home, but if you want to hash out your feud at a Cheesecake Factory or whatever, that’s fine too — as long as talking in public doesn’t get in the way of resolving the issue. Or enjoying that massive menu.)

But before you actually meet…

Frame the conversation.

Setting the tone and intention of your conversation before you meet can radically change the outcome. So before you sit down with your friend, you might want to call or text them and say something like:

“Listen, I wanted to make some time for us to talk because there’s something that’s been bothering me, and I don’t want to let it fester. If we can talk it through and figure out what’s going on, I’m confident that we’ll be totally good, and I can let go of the anger/sadness/hurt/[insert difficult emotion here] that I feel. Thank you for making some time for us — I really appreciate it.”

That script is a great way to set the stage for a tough conversation. It gives the person a heads-up that the conversation might be difficult, but that your only intention is to understand the situation better so you can put it to bed. It also signals that the conflict is surmountable and that there’s a clear endgame — empathy, peace, resolution — which will create some much-needed hope that you guys will succeed in working through the problem.

In my experience, framing the conversation this way in advance — whether it’s days before you meet or in the first few minutes of your conversation — makes a huge difference.

Lay out the problem as you see it.

The next step is to briefly share your perspective on the conflict. I recommend doing this as briefly and calmly as possible, so that you don’t end up escalating the situation any more than is necessary.

For example, you might say something like:

“The other week when you said you’d make that introduction to your old boss about that potential job, and then you didn’t follow through — that really bothered me. I feel like you made a commitment to help me get in there, and then you just dropped it.

“Then, when I brought it up a couple of times, it seemed to me that you brushed me off, and that made me feel rejected and disappointed, like you weren’t taking me seriously. And it also made me wonder if our friendship isn’t as close as I thought.

“So now I’m feeling frustrated about this opportunity and where we stand with each other, and I just wanted to talk to you about it directly so we can figure this out together.”

Laying out a problem in that way frames the issue clearly without belaboring the point or turning the conversation into an opportunity to complain or punish the other person. It signals to the other person that you understand what’s on the table, and you want to work together to solve the problem. It also gives the other person permission to be equally direct with you.

Invite another perspective.

Once you lay out your perspective, give the other person space to share theirs.

“So that was my experience of what happened,” you can say as you wrap up. “I’m curious about yours. If I’m missing something here, I’d love to know. If I misinterpreted your decision, please tell me. I’m all ears. What happened?”

At that point, your job is to listen.

Truly listening to the other person means setting aside your version of events and being open to hearing a different one. It means empathizing with the other person — even if you ultimately disagree with them — and trying to appreciate why they did what they did (or, in this case, didn’t do).

One of the hardest things in life is to be willing to hear a different narrative from the one you’re currently holding. But if you can, you’ll get to a resolution much faster.

As you listen, try to recognize the role you played in the dynamic (even if your response was only a small piece of the puzzle).

Identify factors you might have overlooked because you were too caught up in your own response.

See if their reasons were truly about you, or were mostly in service of themselves (a very common cognitive bias called the fundamental attribution error).

Then, process what you hear. Mirror back to the other person what they just said. Make sure you’re fully understanding them. If you still don’t understand their position, ask them to clarify it. If you disagree with any of their points, now is the right time to respectfully challenge them.

As they respond, go back into listening and empathizing mode. Repeat that process as many times as you need until you both have a clear picture of the other person’s experience.

Explore and resolve the conflict.

From there, you’re in a dialogue. As you discuss your perspectives and feelings, you’ll come to a better understanding of the situation. This could last 30 minutes or three weeks, depending on the complexity of the issue. As long as you guys are getting clearer on the problem and moving toward a solution, that’s time well spent.

A few different outcomes are possible here.

Maybe you’ll find that your injury was real, but that it wasn’t actually personal.

For example, your friend didn’t purposely renege on her promise to introduce you to her old boss. She just realized afterward that she had overpromised, didn’t maintain a strong relationship with her boss, and felt awkward making an introduction after so long. What seemed like a personal slight against you was actually just a product of her own mistakes — a classic example of fundamental attribution error at work.

Or maybe you’ll find that the injury you feel was in fact personal — but that your friend had good reasons for doing what she did.

For example, she acknowledges that she had second thoughts about introducing you to her old boss because she wasn’t convinced that you were actually ready for that job.

Now, that’s a tough pill to swallow. It definitely hurts. But at that point, you have an interesting opportunity to consider your friend’s opinion and see if it might hold some water.

If you take some time to reflect and realize that your friend has a point, then you might discover that she’s actually doing you a favor — by forcing you to confront your limitations and work on them before applying for the job. Your friend should have been more upfront with you, for sure — that’s the part of the conflict she’s responsible for — but she wasn’t entirely in the wrong.

In scenarios like that, you might find that your friend had a “good” reason for “hurting” you. You can hold your disappointment alongside your new understanding.

With time, you might find that the situation doesn’t sting as much anymore, and that you’re actually grateful. (Just one of the many surprising benefits of not jumping straight to a breakup when conflict arises.)

The last outcome is that you realize that your friend really was in the wrong — that you are ready for that job, that you do deserve that introduction — and you can help her see why she should have held up her end of the bargain.

Then it’s on her.

Either she reaches out to her old boss, makes the introduction she guaranteed, and promises to be true to her word in the future — in which case your conflict finds a great resolution.

Or she still doesn’t follow through on her commitment, and then you know that the conflict is still alive.

At that point, it’s back on you.

Either you adjust your expectations of this friendship so you don’t put yourself in a position to be disappointed again — because now you know how this person operates and thinks of you.

Or you decide that you don’t want to stay close with this person, because you can’t be friends with someone who doesn’t honor her commitments.

If that’s where you ultimately land, then all of this back-and-forth wasn’t for naught. It was actually essential. Because if you decide to part ways, you’ll be doing it with a much better understanding of the situation. You can be confident that you’re not prematurely ending a friendship at the first sign of trouble, but redefining the relationship in light of all the facts.

That’ll make it much easier to break up and avoid any regret after the fact — which often happens when people jump straight to ending a friendship at the first sign of trouble.

When Talking Things Out Is Pointless

Before we move on to how to actually break up with someone, it’s worth pausing to acknowledge that there are some conflicts that aren’t worth trying to resolve.

For example, if you discover that a friend is manipulative, toxic, or straight-up dangerous (physically, emotionally, financially), then I would be wary about trying to “work through” that conflict.

In all likelihood, the dysfunction has very complex roots, and you’re not going to be able to fix them. Also, you might be putting yourself at further risk by trying to make the friendship work.

So if you’re dealing with a person who’s highly unstable, emotionally volatile, overtly manipulative, or involved in criminal activity, then your best bet is probably to stay away.

Sure, you could still use the framework above to work through that conflict. And it is possible that the other person will be willing to engage with you and change.

But the chances of that happening, in my experience, are pretty low — especially when it comes to very serious conflicts whose origins go back long before your friendship began.

Another conflict that probably isn’t worth trying to resolve is if the other person holds hateful or toxic positions on the world.

For example, if you learn that a friend is deeply racist or misogynistic, or actively biased against certain people for gross and illogical reasons, I’d probably just let that friend go.

Now, none of these are hard-and-fast rules. Every situation is different. The mitigating factor in all of this, of course, is your history and connection with the other person.

If you’ve been best friends with someone since you were kids, and later in life that person develops some unsavory opinions or gets caught up in a financial crime or something like that, then you have more of an opportunity — and probably an obligation — to talk to them, figure out what’s happening, and hopefully set them on a better path.

Same goes for a friend who’s part of your family, or is friends with your friends, or has a prominent role in your life. Sometimes you do owe certain people more of an effort.

But if you grab beers with a guy from work a couple of times before discovering that he’s the most prolific anti-Semetic memelord on 8chan, then I wouldn’t try to reason with that guy. You guys aren’t longtime friends, and you’re not going to have much luck convincing Chad that his view of the banking system needs some revisting. You’re certainly welcome to — and if you succeed, you’d be doing the world a solid — but you don’t have the same obligation or opportunity to try.

(Plus, if that guy is dangerous on top of it, then you might actually be putting yourself at risk by spending more time with him — even if it’s just a hit to your reputation.)

So take all of these variables into account when you hit a rough patch in a friendship.

Factor in your personal history, your connection, your personalities, their state of mind, how much you care about maintaining this relationship, how much success you’ll have in resolving the conflict, and what the larger stakes of saving this friendship are.

Sometimes the right answer isn’t to try to resolve a conflict before breaking up with a friend. Sometimes the nature of the conflict demands that you skip go and just break up with them.

Determine the degree of the breakup.

One interesting thing about friendship is how different it can look. There’s a much larger spectrum of intimacy in friendships than there is in, say, romantic relationships. Sure, you can have multiple casual partners with varying degrees of closeness, but it’s unusual to have dozens of them over decades. (Not to mention exhausting. Nobody got time for that!). But friendships can easily range from very casual to super close, and they can evolve over time. Which is one of the cool things about friendship.

My point is, you can define a friendship in a lot of different ways. The terms of that relationship, the amount of contact it involves, the degree of intimacy — those are very fluid in friendship.

And you can redefine that friendship whenever you want.

Soft Breakups vs. Hard Breakups

So when you get to the point where you feel it’s time to end a friendship, take a moment and ask yourself what “ending” the friendship actually needs to look like.

Does the conflict warrant a total and formal separation — a “hard” breakup?

Or does it just call for a redefinition of your feelings and terms with that person — a “soft” breakup?

Obviously, some conflicts are so severe that they call for a hard breakup. If your best friend sleeps with your fiancé or something, that’s probably a friendship-ender. (Also an engagement-ender, but that’s a different article.)

But if you find that you have less in common with a certain friend these days, or their behavior is mildly irritating, or the friendship isn’t generating as much value as it once did, then that might call for a subtler breakup — a simple recategorization of that friend in your mind.

In those cases, you might not need to schedule the whole “we’re done being friends” chat. Instead, you can limit your contact, draw a harder boundary around your time, and adjust your expectations for the person. Maybe you only socialize with them in large groups, or keep your friendship to social/email/the phone, or only bring certain topics to them. All of these are fair game in friendship.

Of course, your friend’s response to that move will also factor in here. If you go from talking twice a week to grabbing coffee once every six months, they might ask you what’s changed.

In that case, you might have to be more explicit about how you view your friendship — which in some cases could mean escalating from a soft to a hard breakup. (“Hard,” now, in both senses of the term. This stuff ain’t easy!)

So as you transition a relationship, ask yourself: “Do I want zero contact with this person, or just less contact? Do I need the other person to know explicitly where we stand, or can the other person pick up my cues?”

Both are perfectly acceptable choices. But really consider them before you turn the breakup up to 11.

A Brief Word About Ghosting

I could write a whole article about ghosting, but it’s worth touching on ghosting as a way of breaking up with a friend in the modern age.

In short, I think ghosting a friend is a fair move in certain limited situations.

One of those situations is when you’ve only seen the other person once or twice, and you don’t have much of a connection. In other words, when this “friend” is actually just a very new acquaintance.

Ghosting can still be hurtful in those contexts, but given today’s social mores, ghosting a brand-new contact is usually an acceptable way of saying, “Sorry, but there’s no future here.”

And in those cases, parting ways is hardly a “breakup,” because the relationship never really got started in the first place.

Another scenario where ghosting is appropriate is — again — if the other person is behaving egregiously or dangerously.

For example, if you find out that your friend is actively hurting you or is involved in activity that could compromise you, then your best bet is probably to just cease communication. They’ve made their bed. By trying to formally break up, you might be exposing yourself to even more harm.

But once you reach a certain degree of intimacy with someone, ghosting is pretty uncool (in my book, anyway). The more we accept ghosting as an acceptable way of “breaking up” with people, the less skilled we become at handling these difficult conversations. Then we avoid them further, which makes us rely on ghosting even more, and the cycle just reinforces itself.

My policy is to communicate openly with friends about the nature of your relationship if the other person isn’t getting the message. I know it’s awkward. I know it’s hurtful (often for both of you). But it’s also a sign of basic respect.

If you’re ever in doubt, my advice is to not ghost. But know that you usually don’t have to be super formal when it comes to a relationship in the very early stages. Ghosting a questionable contact you met on Bumble BFF is probably fine. Ghosting a friend of five years is hurtful and conflict-avoidant.

Have the conversation.

Once you’ve decided that the right move is to end a friendship, it’s time to actually have the conversation. This is where things can get tough — which is why you clicked on this article in the first place!

The first step is to make a plan.

Prepare your message.

In all likelihood, this conversation will be difficult. So before you actually break the news, prepare for some degree of awkwardness, pain, and possibly even further conflict. You’ll also want to be ready for a range of responses to the news — acceptance, sadness, anger, projection. Every personality responds differently to this kind of news.

It can also be helpful to rehearse a brief script in advance, so that you don’t have to scramble for words in the moment. In that script, I would articulate your decision, the reasons for your decision, and your intention in redefining the friendship.

“Thanks for making some time for me,” you might say. “What I’m about to share might be difficult to hear — it’s difficult for me to say, too — but I feel that it’s important to be upfront with you.

“Over the last few months,” you might continue, “I’ve found a few of your choices very problematic. When you caused a scene at my birthday party, that made me really concerned about your behavior and how you treat me and my friends. When you agreed to help me prepare for those job interviews and then ghosted me for three weeks, that was really disappointing.

“Overall, I don’t feel that we share the same values or goals anymore. I tried to talk to you about those incidents, and we didn’t make any progress, and that’s led me to question whether this relationship still makes sense.

“I’ve given all of this a lot of thought,” you can conclude, “and I feel it’s best that we stop spending time together. Please know that my intention here is not to dredge up old stuff or hurt your feelings. I just want to be upfront so that things aren’t confusing. If you want to talk about any of this, I’m open to doing that for a few minutes. But this is the decision I feel is best right now.”

Whatever the specifics of the breakup are, that script will pretty much work in any scenario. Start with the headline. Briefly touch on your rationale. Then deliver the news.

And while you do that, be as respectful and non-confrontational as possible.

Choose the medium.

Different relationships require different approaches. If you’re breaking up with a friend of 10 years, you should probably do it face-to-face — you owe it to the other person. But if you’re breaking up with someone you work out and grab beers with once a month, you might be able to deliver the message by text (if you need to break up with them at all).

You also have to consider your needs in this conversation. If you know that breaking up with your long-time friend is going to be highly emotional and you’re going to struggle to find the right words, then maybe it’s better to send a thoughtful email.

But when you’re sending a breakup letter to someone you’re close with, I think it’s always nice to invite the other person to have one last live conversation.

“If you want to discuss any of this in more depth, I’m happy to come to your house or talk on the phone,” you might say. Then you get the best of both worlds — the control of a letter and the respect of a conversation.

Find your compassion.

Breaking up takes a lot of courage. It also requires you to take your own needs seriously — and to prioritize those needs over what the other person wants.

Which can also make the breakup conversation feel a little cruel.

So while you deliver this tough piece of news, try to stay connected to your empathy.

“I’m really sorry if this is difficult to hear,” you might say. “I apologize for the part I’ve played in our conflict,” you could add. “Please know that my goal isn’t to punish or hurt you in any way. It’s only to be honest about where we stand.”

These phrases really soften the blow. They also treat the other person with a baseline respect. And it’ll be a lot harder for your friend to lash out when they see that you’re treating them with kindness in a tough moment.

Manage your emotions.

Your compassion also comes through in how you deliver the news.

I recommend speaking in a gentle tone and choosing language that isn’t highly charged. I also wouldn’t use the breakup as one last chance to get a few digs in. It’ll take some work to set your feelings aside while you just focus on the message, but it’s worth checking them at the door as much as possible.

Of course, if any volatile emotions do crop up, then I would acknowledge them, invite them into the interaction, but don’t feed them more than you have to.

“As you can see, I’m still very worked up about this,” you might say if you start to get angry or cry during the conversation. “I feel hurt by what you’ve done and I’m sad that we haven’t been able to resolve it. But this is why I’m sure that parting ways is the right decision.”

Something like that can help keep the conversation on track.

Sometimes the feelings that creep in during a breakup are subtler than rage or tears. For example, you might find yourself overcome with guilt or fear about what you’re doing — which are also very normal responses.

Again, acknowledge the feeling (at least to yourself), recognize it as a response to delivering a tough piece of news, and don’t let it derail your goal. Later you can explore those negative emotions and see what they’re trying to tell you.

But in the moment, you have to quarantine these reactions from the message so you can stay focused on the facts.

Make it a conversation — up to a point.

After you deliver the news, invite the other person to respond. But if you’ve really done all you could to resolve the issue before this breakup, then there probably isn’t much to say. It’s just a respectful move to give the other person a chance to speak.

Of course, this could invite a ton of unnecessary back and forth. So I recommend putting some boundaries around your time.

If you’re breaking up with a close friend, you might owe them a few hours of your time to provide clarity and comfort — but not two more months of late-night phone calls.

If you’re breaking up with an acquaintance you grab dinner with every couple of months, a 20-minute conversation by phone is probably appropriate, and I wouldn’t spend the next six weeks texting with them about it.

At a certain point, these conversations stop being productive. It’s perfectly fine to say, “I think we’ve both said all there is to say, and I’m not sure how much we’re going to accomplish from here on out. I’m sorry this has been difficult, but I need to go now.”

Again, stay connected to your compassion while you do this, and you’ll hit the right note.

Process the response.

As you listen to the other person’s response, try to appreciate what this breakup is like for them — without letting their reaction throw you.

For example, if your friend breaks down in tears, that might be an appropriate response to the breakup, and it will probably be quite difficult for you to watch. (This is where the tough emotions, like guilt, really kick in.)

Your job is to have compassion for their pain, allow them to move through that phase of their reaction, and still stay connected to your experience. As we talk about on the show, another person’s negative response isn’t a referendum on whether you’re right or wrong.

Or, to take another common scenario, the other person might fly into a rage at the news, and maybe even project their anger onto you. Here, too, your job is to give them some space to process the news without being intimidated by their response. Again, their rage doesn’t mean that you’re wrong. It just means that your decision is making them angry.

Now, let me just acknowledge that this stage of the breakup conversation is extremely difficult. It goes against all of our programming to make another person suffer, and we’re generally wired to wonder if we’re in the wrong if someone else is upset.

But this is yet another reason that it’s crucial to try to resolve conflicts before you end a relationship. If you don’t make a genuine effort to fix things, then you might suddenly question if you’re actually making the right decision during this conversation. Then you either have to backpedal and qualify your stance, or you’ll leave the conversation wondering if you made a huge mistake. By the time you end things, you want to feel very secure that it’s the right move.

Bottom line: Don’t try to resolve a conflict while you break up with someone. Try to resolve the conflict first, then escalate to a breakup if necessary. That way, you’ll feel much more centered when it comes time to deliver the news.

End on a good note.

Let’s face it: very few breakups end on a positive note. But there are better and worse ways to wrap up the whole “I never want to see you again” conversation.

For example, as you wrap things up, you might say, “Look, I know this conversation has been hard. Despite everything, I want to thank you for the good parts of our friendship, and I wish you nothing but happiness and success.”

A message like that can go a long way in softening the blow of the breakup. It can also protect your reputation. People are a lot less likely to talk smack about you if you met them with compassion as you parted ways. I’ve seen that firsthand, in my personal life and in business.

Of course, sometimes these well wishes aren’t appropriate. If a friend slept with your partner or stole money from you or gossiped about you behind your back, then you don’t need to say something untrue to make things better. Some breakups just end on a bad note, and that’s how it has to be.

But in less severe breakups, finding a note of positivity is always a good policy.

Hold your boundaries.

Once you end a relationship, you have to commit to a new set of terms. It might be tempting to reach out to the person afterward — perhaps out of guilt, regret, or nostalgia. But that would only be backsliding.

So when you decide to redefine a friendship, you also have to get clear with yourself on what that relationship will look like in practice. Decide how much contact (if any) you should have with this person, how you’ll handle things if you run into them in the future, and what you should and should not share with them. You almost have to make a pact with yourself about how you’ll behave within your new parameters.

This is especially important in the first few days or weeks after a breakup — especially if you’re parting ways with a longtime friend. You’ll probably experience a lot of grief in that aftermath, and you have to be prepared to hold those feelings without acting on them.

But while you’re going through your grieving process, your friend is going through their own. So you also have to decide how you’ll respond if they try to reach out to you.

If your former best friend texts you wanting to talk again after the breakup, will you engage? If so, what will you say? Will you give them more time and energy, will you politely tell them you can’t talk anymore, or will you just ignore them?

These boundaries are crucial. Ending a relationship takes a lot of work. But honoring those new terms takes discipline.

When to Rekindle a Friendship

Another question I get asked a lot is: “Should I start up a friendship again with someone I cut off in the past?”

That’s a familiar scenario in the dating world, where people often break up and get back together a few times before remembering that there’s a good reason they broke up in the first place. But in the friendship world, the rules can be fuzzier.

My policy on rekindling a friendship you’ve put to bed is basically this:

Sure, you can do it. But I would be very thoughtful about how you do it. And I would be damn sure that this friend has changed in meaningful ways — and that you and this person have each addressed the roots of the conflicts that led to your breakup.

For example, let’s imagine that you ended a friendship with someone who had a drinking problem and wasn’t showing up as a healthy, consistent presence in your life. Years later, that person reaches out with an apology, and asks to be friends again.

If that person went through treatment, has been sober for a long time, and is actively engaged in their recovery, then that counts for a lot. If that person has also done a lot of work on themselves, understands what drove them to be a toxic friend, and is demonstrably committed to showing up for you in a new way, then that’s encouraging. And if you guys still have values and interests in common, then you guys might have a great friendship again.

In that scenario, it’s almost as if you’re dealing with a completely different person. And that could be a good reason to rekindle the friendship — if, of course, you feel that the friendship would be a positive one.

But now let’s imagine that you distanced yourself from a fun but unpredictable colleague who took credit for your ideas in meetings and talked smack about you behind your back. A couple of years later, you run into each other at a conference and have a friendly conversation, and he invites you to drinks the following week. He apologizes for “all that stuff” back at your old company, and he assures you that he’s “mellowed out” since then.

Do you reengage?

In my book, probably not. Not immediately, anyway.

First of all, the guy in that scenario isn’t showing concrete signs of growth. He hasn’t apologized for his dysfunctional behavior, and he’s downplaying the severity of what he did. And he seems to be more interested in just picking up the same friendship again, without taking the time to discuss what happened between you in the past.

Now, you might decide to hop on the phone with this guy and suss him out — and maybe that’s worth your time. When you do, maybe you bring up what happened at the old company, and that you want to know why he did what he did. His response to that question will be very telling. Either you’ll realize that he is contrite and interested in a different relationship with you. Or you’ll realize that he’s not eager to show you that basic respect, and he’s still the same guy.

If you do decide to rekindle an old friendship, though, it’s always a good policy to go slowly. I wouldn’t jump right back into the same amount of contact, same degree of intimacy, or the same activities that you used to.

Instead, start slow. Spend an hour together, see how it goes. Ease into certain topics and study how they handle them.

Most importantly, give yourself some time to check in with yourself about how this friendship is feeling on the second go-around.

Are you experiencing the same questions, concerns, or feelings you did last time?

Or are you finding a new experience with this person — either because you’ve changed, they’ve evolved, or both?

It’s no different from a romantic relationship, really. All relationships end up the same way unless both parties have gone through meaningful growth. If they haven’t, then there’s no reason to think that rekindling the friendship later will lead to a different result.

So be thoughtful and check in with yourself. That’s really the only rubric that counts.

Learn from the experience.

Breakups are very eye-opening. In addition to learning a lot about how you handle difficult conversations, you also develop a clearer understanding of the people you actually want to keep in your life.

So once you go through a transition like this, I recommend taking some time to do a postmortem on the friendship, so you can grow from the experience and avoid similar conflicts in the future.

Here are a few powerful questions to ask after a friend breakup:

What drew me to this person in the first place?

• What qualities or behaviors did I find interesting, useful, or attractive?
• Which events or experiences brought us together?
• What parts of myself did I get to experience (or avoid) by being friends with this person?

What went wrong in this friendship?

• Where did our values, goals, or priorities diverge?
• Which conflicts did we run into?
• What role did I play in those conflicts (even if it was just failing to speak up about what bothered me)?

What red flags did I miss or ignore?

• Did I have any indication of future problems along the way?
• Did I notice any troubling behavior that I dismissed or rationalized?
• Why did I overlook those qualities?

What role did this person play in my life, and what role did I play in theirs?

• Was the relationship open, fair, and equal? Or was it manipulative, unclear, or one-sided?
• Did one or both of us fall into a dysfunctional pattern (e.g., caretaking, enabling, playing the audience, propping the other person up, comparing oneself, etc.)?
• What did I look to this person to provide me (emotionally, intellectually, financially, logistically, etc.)? What did they look to me to provide them?
• Were those healthy needs and expectations, or were they unrealistic or dysfunctional?

Answer those questions, and you’ll learn a ton about yourself and how you relate to other people. I recommend writing them down and even discussing them with a trusted friend or counselor, so you can get even better insights into how this friendship operated.

Then, use those new insights to make better choices about your relationships going forward.

If you find yourself gravitating toward a similar personality to a friend you broke up with, a few alarm bells will be going off. And this time, you’ll have the self-awareness to say:

“Hang on, this feels familiar. I’m sacrificing my own needs here. I’m spending a lot of time playing the audience to someone else’s narcissism. This person makes me feel needed, but really I’m just propping her up and distracting myself from my own goals. Isn’t this what happened last time? Is this really what I want?”

From there, you can make a more conscious decision about whether you want to be close with this person.

You can cut the friendship off before it gets too deep, and save yourself a ton of conflict and heartache down the road.

Or you can decide that you do want to pursue a friendship with this person — but this time, you’re going to show up differently. When something bothers you, you’re going to speak up. When they dominate conversations, you’re going to assert yourself more, or put some boundaries around your time. Maybe the entire friendship will be different when you start operating differently within it.

But none of that is possible until you study the patterns of your failed relationships. This is just as true for friends as it is for romantic partners.

In fact, this might be the most important part of breaking up with a friend:

Figuring out why you ultimately had to break up with them, so you can choose friends you don’t want to break up with.

That’s the one huge gift of these tough transitions.

[Photo by Tyler Nix]