How to Have a Breakup Conversation That Ends Well

This article is an excerpt from the Shortform book guide to "Necessary Endings" by Henry Cloud. Shortform has the world's best summaries and analyses of books you should be reading.

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Do you need to end a relationship with someone in the best way possible? What is the key to having a healthy breakup conversation?

Breaking up with someone is never easy. There’s always that worry that they won’t take it well, or will try to convince you that you’re doing the wrong thing. If you know deep in your heart that you have to end the relationship, you should prepare for the conversation beforehand.

Let’s look at how to have a breakup conversation with someone.

Prepare for the Ending Conversation

When it comes time to end a relationship, thoroughly prepare for the ending conversation by learning how to have a breakup conversation. In Necessary Endings, Henry Cloud contends that people often go into these conversations underprepared, which leads them to make mistakes that make the process more difficult and confusing for everyone involved.

The first step in preparing for an ending conversation is to set goals for what you’d like to accomplish during the conversation. According to Cloud, people who enter these kinds of conversations without clear goals in mind often end up waffling or letting the other person convince them to change their mind. For example, if you decide to fire an employee whose role has become obsolete, your goal might be to clearly communicate that the employee is fired, while also thanking them for their time at the company and letting them know that you’re open to being listed as a reference. With these goals in mind, it’ll be easier to stay on task in the heat of the moment.

Once you’ve set goals for the conversation, it can help to rehearse. Endings can be emotional, and you may find it difficult to remember everything you wanted to say when the time comes. While it might sound silly, writing a script and practicing it can help you feel more confident later on.

When writing your script, be sure to focus on the problem in the relationship, not the person. According to Cloud, focusing on the other person’s flaws can make them feel attacked, which may result in a heated and uncomfortable conversation. By focusing on the relationship’s issues, you’ll maintain clarity without upsetting the other person as much.

During the conversation, try to balance empathy with firmness. Cloud says people are more receptive to ending conversations when you approach them gently. However, at the same time, take care not to be too gentle, as this might give the other person the impression that you aren’t serious. Don’t be cold, but don’t leave any wiggle room either.

More Advice for Effective Endings

There are a variety of perspectives on the best practices for ending personal and business relationships. In Difficult Conversations, Douglas Stone, Bruce Patton, and Sheila Heen argue for the importance of separating impact from intent. Stone, Patton, and Heen note that people who hurt you don’t always intend to and aren’t usually bad people. Separating impact from intent can help you maintain empathy for the other person as you end things.

Along with separating impact from intent, as you set goals for the conversation, remember that you can’t control the other person’s reaction. No matter how well you prepare or how clearly you communicate, how the other person reacts is up to them. Keep this in mind, and remember that it doesn’t reflect on you if the other person becomes upset or refuses to accept the ending. To avoid being upset if the other person reacts poorly, set goals that focus on your own communication and not on the other person’s reaction.

Once you’ve set goals for your communication, it’s time to practice communicating. In addition to rehearsing with a friend, experts recommend spending time by yourself to prepare for an imminent ending. During your solo rehearsal, you can coach yourself and prepare mentally for the task ahead. Spending time preparing alone can help you to understand and accept your role in the failed relationship, as well as giving you time to further meditate on why the ending is needed.

As you rehearse for an ending conversation, write a script that succinctly addresses your issues in the relationship. Take care not to over-explain your reasoning. Getting too detailed when explaining your reasons for ending a relationship creates room to argue, and may bring up hard feelings that can lead to escalation.

Once you’ve taken all the necessary steps to prepare for the conversation, let your loved ones know what’s about to happen. By letting your loved ones know in advance, you’ll ensure that you have the support you need when you come out of the conversation.

Take Time to Process and Reflect

After ending a situation or relationship, take time to process your feelings and reflect on the situation and its ending. Cloud argues that taking time to process your emotions after an ending is an essential part of the process. Processing and reflecting on the situation can help you to learn from it. As you reflect, make an effort to understand what went wrong. Doing so will help you avoid similar situations in the future. 

(Shortform note: While it’s important to reflect on relationships after they end, experts caution against hashing out the relationship with your ex. It can be tempting to meet up with your ex to discuss exactly what went wrong, but these meetings only lead to more conflict, and in some cases, they may even lead you to reopen a relationship that you worked hard to end.)

By contrast, when you avoid reflecting on your feelings, you’re liable to make the same mistakes again. Not only this, but when you avoid processing your feelings and instead choose to avoid them, you’re also more likely to make impulsive decisions to distract you from your pain.

(Shortform note: To avoid making impulsive decisions after ending a romantic relationship, some experts suggest setting aside a period of time to take a break from dating. Taking a break from dating gives you time to focus on yourself and on unpacking your feelings about the ending. Explicitly deciding to stop dating helps ensure that you don’t allow yourself to be distracted by a sudden rebound fling.)

How to Have a Breakup Conversation That Ends Well

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Here's what you'll find in our full Necessary Endings summary:

  • That pulling out of a bad situation is the best way to move forward in life
  • How to assess which situations and relationships need to end
  • How to make sure that your endings stick

Katie Doll

Somehow, Katie was able to pull off her childhood dream of creating a career around books after graduating with a degree in English and a concentration in Creative Writing. Her preferred genre of books has changed drastically over the years, from fantasy/dystopian young-adult to moving novels and non-fiction books on the human experience. Katie especially enjoys reading and writing about all things television, good and bad.

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