How to Break up with Someone Nicely – The Art of Charm

One of the most common scenarios I encounter as a coach is working with guys who are in mediocre relationships. They’re not thrilled about their significant others, yet they stay with them, month after month, year after year. Why?

Sometimes it’s a shared history that keeps them together. In other cases, it’s the fear of being alone. (On the Periodic Table of Reasons for Being With a Girl, that fear might be the most common element in the romantic universe. There is no worse reason for staying in a relationship than your fear of not being in one at all.) But when I talk to guys about why they stay in relationships, there’s one reason that pops up again and again: They simply don’t know how to break up with a girl.

It sounds so elementary, but when you and your lady have serious history, or live together, or share friends and possessions, or you’ve just never had to end a serious relationship before — well, it’s perfectly normal to not have the slightest idea how to end things.

The first time I heard about this phenomenon I was confused. The second time I was surprised. The third time, I realized there was a real pattern of fear and anxiety here.

So as you approach the subject, I wanted to share a little bit more about what we’ve learned about the delicate process of breaking up. Consider this the CliffsNotes version of how to break up with someone nicely, while maintaining your sanity and integrity.

Tips on how to break up with a woman

Rule number one: Make sure you want to break up.

Before determining how to break up with someone nicely, make sure that breaking up is definitely what you want to do. You can go back to a relationship, but that is often awkward, ambiguous and potentially dangerous. It’s far better to wait and get a handle on what you truly want than to try to get back together.

One easy way to determine whether you want to still be together is to make a sort of balance sheet. Take a piece of paper and divide it into four quadrants: Why I should break up, why I shouldn’t break up, why I should stay together, why I should not stay together. There’s going to be some overlap between the four quadrants. But when you look at them all as a whole, it can help you to make a final decision when you’re on the fence.

And don’t be afraid to talk to your trusted friends about the matter. But remember this: If you have one friend in particular who listens to you gripe about your significant other, he’s probably not the best person to ask for advice on this subject. Instead, go to a friend who is more neutral, someone who doesn’t know a lot about the conflicts in your relationship. The one friend you have as a go-to for unpleasant discussions about your girlfriend is almost certainly going to tell you to break up because he has a skewed and unbalanced perception of the relationship.

Between your own self-reflection and the unbiased advice of your trusted friends, you will be able to decide if breaking up is, in fact, what you need to do.

Rule number two: Do the deed like a gent.

Once you’re sure you actually want to break up, you must follow through and do it. Sadly, a break-up isn’t a Band-Aid you can slowly peel off. It’s something you have to rip off in one fell swoop. Again, acknowledging that all situations are different, there are some general guidelines when it comes to this process. We constantly get asked how to break up nicely. It is never an easy task.

First, I’d recommend that you have “the talk” in public, or at the very least in a neutral location. For one, having it in public helps you to avoid the temptation to have breakup sex, which you might enjoy while it’s happening, but, I assure you, you will almost certainly regret it as soon as it’s over.

More importantly, meeting on neutral territory (a coffee shop, a park, the library) allows you to make a quick exit if things go wrong. It’s normal for anyone — including you — to become emotional and behave in a way that seems like “overreacting.” You, however, don’t have to hang around while she does that. If you’re on neutral territory, you can leave whenever you want. If you’re in your apartment, you’re stuck in a highly charged space that is difficult to exit.

I’d also go into the conversation knowing what you want to say. What you communicate should be mostly about you and your feelings. When you make it about you and how you feel, there’s no room to argue. She can’t “debate” whether you’re happy in the relationship. You either are, or you’re not. That is empowering and liberating and keeps the conversation in a grounded, authentic place. It also avoids the drama that comes by making a break-up conversation about the other person. Bring specific examples. She’s going to want to know why. While you’re not obligated to tell her, it’s a good idea to help her understand why this breakup is happening.

Some guys go as far as rehearsing their breakup with a trusted female friend. This can be a little awkward, but it can make all the difference in the world. Ultimately, you should do whatever works best for you.

Finally, set some kind of time limit. You don’t want to sit there all day, rehashing every detail of the relationship. You want to get in, deliver the message, and go about the rest of your day. This depends on how long the two of you have been together, of course, but you still want to have a mental time limit. When the conversation is over, tell her you to have to be somewhere else (even if you don’t), pay for her latte, and politely leave.

Remember: Taking the high road doesn’t mean being a martyr. You don’t need to “lose,” suffer or get hurt in order to be the bigger person. You are winning, avoiding unnecessary pain and minimizing the damage on both sides by taking the high road. That’s why handling the conversation like a gentleman is so important.

Rule number three: Always take the high road.

If my advice about breaking up could be boiled down to one guiding principle it would be this: Always take the high road. Especially if you’ve been hurt, it’s easy to think that taking the low road — by insulting her, complaining about the relationship, fighting over the past, and hashing out the uglier parts of the relationship — is the right thing to do.

But it’s not, for two key reasons.

First, anyone who works in customer service knows that unhappy customers are far more willing to talk about your business than happy ones. Put in more direct terms: If you’re a jerk, she’s going to tell everyone willing to listen. Even if you live in a big city, chances are high that what she has to say will eventually come back to bite you.

But even if it doesn’t, do you want someone going around bad-mouthing you about things that you totally deserve to be badmouthed about? Of course not.

The other reason to take the high road is the regret you will feel afterward. I’m not going to lie: You will wake up in the middle of the night wishing that you’d taken some shots at her when you still had the chance (especially if you came out of an unhealthy and destructive relationship). That can go on for a months, and might even happen years later.

But you’re going to have even more sleepless nights if you do the wrong thing. Calling her out, advocating for your version of the relationship, revising details of your past — that post-mortem might feel good at the moment, but in the long term it’s going to rot your soul. Better to have a few months fantasizing about how you could have burned her rather than a lifetime wishing that you hadn’t.

Rule number four: You can’t be friends… yet.

Every guy likes to fancy that he and his ex are going to be friends after the breakup. Don’t count on it. At the very least, the two of you are going to need a lot of distance to heal. At some point in the future, the two of you might be friends, but don’t expect that to happen immediately.

From your perspective, you’re going to need some room to put yourself back together. You need space and autonomy to reflect and process and recover. From her perspective, she’ll need time to understand your reasons for breaking up and how to rebuild after you’re gone. Both of you need and deserve that distance in order to move on.

Eventually, if your personalities and circumstances allow, you will be able to reconnect and be friends. If that happens, it will be because you gave each other enough space after the break-up. Friendship is possible when you both recover effectively, but don’t impose the requirement of friendship on the break-up from the start. Allow it to develop organically over time by accepting that you won’t be friends immediately. And if it never happens, understand that that is part of the break-up process: Sometimes, relationships can only take one form.

Because at the end of the day, there is no easy way to break up. But if you’re considering it, you owe it to yourself to make the right decision. You always want to be careful with the feelings of other people, but not at the expense of yourself and your own autonomy and happiness. So prepare for this conversation, take the high road, and be the person who successfully transitions the relationship without falling into the usual pitfalls of a break-up. It’s a crucial ability and an essential part of managing relationships.

For more on how to break up with someone nicely (i.e. without sacrificing your dignity), be sure to explore the full wealth of dating and breakup resources on our blog.