Dealing with Breakup Regret

This article is based on the Reimagining Love podcast episode “Dealing with Breakup Regret.” To listen to this episode, click here.

Welcome back to the blog! Today’s topic is “Dealing with Breakup Regret.” Here’s the scenario:

  • You were in a relationship.
  • There was distress, or a rift, or chronic problem you couldn’t get through.
  • You ended the relationship.
  • Some amount of time has passed, and you’re now experiencing Breakup Regret.

Breakup Regret isn’t a scientific term, or even a clinical one. It’s a term I’m using to capture that knot in your stomach that says, “I think I’ve made a terrible mistake.” In this article I am going to talk about why you might be experiencing Breakup Regret, and offer some strategies for what you can do with that pang. There’s the feeling, and there’s the what-to-do about the feeling. We will explore both.

Let me be clear right up top. I am sure of two things:

  1. I am sure this discussion will offer you some perspectives and some strategies.
  2. I am sure this discussion will NOT tell you what to do—reach out to reconcile or remain apart. I would never disrespect you in that way, acting as if I know what is best for you. I don’t have your context or the details of your story. This conversation may help you feel more clear about staying the course or pivoting and trying to rebuild with your ex. But your clarity will come from a place inside of YOU—not because I advised you in one direction or the other. Furthermore, if you have been a reader for a while, you know that I don’t make hierarchies of love stories. Some love stories are very linear— people move in stepwise fashion through the stages of commitment. Some love stories are rather curvy— they have detours in the form of breakups, and they start again. If you listened to the Toddcast, you know that Todd and I had a couple of breakups back in the day, initiated by yours truly, so I am especially in no place to judge a curvy love story. The focus of this article is making sense of the experience of Breakup Regret and providing you with some strategies for how to cope with the feeling. What I am NOT going to do here is talk about a framework for how you might create a Version 2.0 with your ex. That is beyond the scope of today’s show. But, spoiler alert, I am going to talk about Second Chances in a future blog post, so you can stay tuned for that!

Let’s dive in and look at why you might be experiencing Breakup Regret. 


I am going to talk about six possible causes of Breakup Regret:

  1. Grief
  2. Dating is difficult
  3. The Safety/Novelty Dialectic
  4. Idealization of ex.
  5. Reactive Breakups
  6. Difficulty trusting yourself

As we go through these, know that I am not making any value judgments. I am describing a set of phenomena. I am putting language to what may be your experience so you can make sense of it. From that place of groundedness, it will be much easier for you to choose your next wise step whether that is to continue to heal via staying apart or whether that is reaching out to initiate contact in the hopes of reuniting. After I talk through these six possible root causes of Breakup Regret, I will provide you with some strategies and ideas about how to cope with Breakup Regret. 

What causes Breakup Regret?

(1). Grief.

The first possible cause of Breakup Regret is grief. I am making an assumption throughout this discussion that the person experiencing Breakup Regret is the person who was the lead in the breakup, the person who initiated the breakup. Here’s something we don’t talk nearly enough about: the lead grieves. The one who chose to end the relationship also experiences grief. You likely feel sad that you were not able to have the relationship you had envisioned. You likely miss that person and the positive times you had together. You likely feel sad that your choice to break up with them hurt them. Unless you are a sociopath, you are not comfortable or happy or pleased knowing that they are having a hard time.

Grief can bleed into Breakup Regret because the line between “I miss them” and “I want them back” is very thin. Why? Because emotions are bodily states. Bodily states create action potential. In other words, bodily states call us to do something. The more intense your grief, the more you are primed to experience Breakup Regret. Your Breakup Regret might be a symptom of or an extension of your grief.

(2). Dating is difficult.

The second possible cause of Breakup Regret is the fact that dating is hard! One of love’s central ironies is that:

  • Those of us who are in an intimate relationship, even a happy one, sometimes wish we were single. 
  • Those of us who are single, even happily single, sometimes wish we were in an intimate relationship. 

It is easy to idealize the experience of the other. The single person in a group of married people feels that complex mix of envy and fascination oozing off their partnered friends when they talk about their single life or their dating experiences. And anyone who is partnered has had that moment of awareness when their single friend experiences a pang of jealousy over their story of partnership.

But, it can be really jarring to be single again, especially if you were in a relationship for a long time. If you broke up with your partner, it was for a reason. You were moving away from pain. You were, very likely, hoping to move toward pleasure. You were excited to have a first date. You were perhaps looking forward to a first kiss. Maybe when you anticipated single life, you had tried to be rational and tempered and you reminded yourself that dating isn’t easy. But maybe that was more of an abstract idea versus something you were really preparing for. And maybe your dating experiences post-breakup have been worse than you had even anticipated them to be. Dating has always been hard, but modern dating is really hard. So here’s the thing: the more frustrated you are by your dating experiences, the more enticing your ex begins to look. Your ex might feel then like respite from whatever aspect of single life is harder than you thought it would be. Your Breakup Regret might be a symptom that tells you something about your dating experiences:

  • You’re surprised at how difficult dating is.
  • You’re feeling disappointed in how dating again is going for you.
  • You’re feeling burned out on dating.

(3). The Safety-Novelty Dialectic

The third possible cause for Breakup Regret is what I am calling the Safety-Novelty Dialectic. Reminder for those who might be a bit newer to my work: dialectics are these both/and spaces where we are challenged to hold two competing truths without foreclosing on one or the other. A dialectic is a space where we say both this and that, rather than saying either this or that.

In her seminal book, Mating in Captivity, my brilliant friend, Esther Perel described the central tension or dialectic of intimate relationships. Human beings have twin needs: the need for safety and the need for novelty; a Safety-Novelty Dialectic. We want both safety and novelty, and we want it from the same person, our partner, in the context of this one relationship. The Safety-Novelty Dialectic goes like this:

  • On the one hand, we want to feel seen and known. We seek ritual and comfort. We want to feel safe and secure.
  • On the other hand, we want to feel excited and surprised. We seek novelty and adventure. We want to feel alive and mysterious.

Your breakup may have been your attempt to resolve the Safety-Novelty Dialectic because the dialectic could not be held; you were not able to feel both safe and excited with the same person. There are two ways that this could have broken down: too much safety or too much novelty.

  1. TOO MUCH SAFETY: It may be the case that when you were in your relationship, rather than feeling safe and comfortable, you felt flat and disconnected. You were yearning for novelty, adventure, and aliveness. You broke up because you were unable to see a path to enlivenment within the relationship. However, now that you are broken up, it’s like the pendulum has swung too much in the other direction. Instead of being adventurous, your single life is feeling unsafe or chaotic or discombobulating. Your Breakup Regret—your desire to get back together with your ex—is a desire to escape how unsettling this feels.
  2. TOO MUCH NOVELTY: Or perhaps, it went the opposite way. When you were in your relationship, rather than things feeling exciting and new, they felt unpredictable and therefore unsafe. You were yearning to feel calm and steady. You broke up because you were unable to see a path to safety within the relationship. However, now that you are broken up, it’s like the pendulum has swung too much in the other direction. Instead of being safe, your single life is leaving you feeling lonely, isolated, and disengaged. Your Breakup Regret—your desire to get back together with your ex—reflects a desire to feel some charge again.

(4). Idealization of ex

The fourth possible cause of Breakup Regret is the idealization of your ex. When you were making the decision to end the relationship, the relationship felt problem-saturated to you—you were likely all-too-aware of your partner’s flaws. In making the decision to end, those flaws had to be squarely in the center of your view in order to justify or align something so big as an ending. Otherwise, there would be too much cognitive dissonance. Cognitive dissonance is when there is a breakdown between your beliefs and your actions. You cannot break up with someone if the belief is, “This is a good and healthy relationship” or “This is my soulmate.” Your beliefs must align with your actions. You need to believe this is not the person I want to be with or the problems we face are insurmountable or our timing isn’t right. 

What’s tricky is that with time and distance, your memory of your ex and of your relationship dynamics may shift. With time and distance, it is much easier to hold onto their redeeming qualities. This is not unlike when we lose someone to death: our memory of that person becomes more idealized over time. Research even backs this up. Let me share two science-backed findings:

  • 2016 research from the journal, Emotion and Motivation, found a “pervasive motivational tendency to praise and idealize the deceased, which serves to reduce death-related distress.” These researchers had participants think about either someone they were close to or someone they were not close to. Group 1 was told to imagine that this person had died and then write about that person. Group 2 was just told to write about that person. The descriptions given by Group 1 (the group where they imagined that their person had died) were significantly more positive and less negative than the descriptions given by Group 2. These effects were found regardless of whether the participants wrote about someone they were close to or someone they were not close to. The researchers said that although this study was just about people imagining that someone had died, their findings are consistent with research about how people eulogize or remember people who have actually died. So idealization is an attempt to cope with loss.
  • Separate but related to this is the finding that our memories are notoriously unreliable. One example of how our memories about certain experiences morph based on the quality of those experiences is something called the Fading Affect Bias. This is a phenomenon that is well-established in the field of psychology. The Fading Affect Bias refers to the fact that emotions associated with negative events fade faster than the emotions associated with positive events. This again is a coping mechanism; it is adaptive. A 2019 study published in the journal Psychological Reports found that higher levels of Fading Affect Bias were associated with higher levels of Grit. In other words, you ended your relationship because it was dissatisfying or negative, but your brain is primed to have those negative memories fade pretty quickly, in an effort to protect you from pain and help you feel resilient. However, this tendency for memories to become romanticized is also then potentially being the cause of your Breakup Regret.
  • Researchers have also found evidence of what they call the Rosy View phenomenon. People’s recall of previous events tends to skew more positive than what they actually experienced at that time.

So, the bottom line here is that memory is fungible, and you, like all of us, are at risk of romanticizing what was. The story of your relationship and your perception of your ex is shifting inside of you in a way that is triggering Breakup Regret

(5). Reactive Break Up

You might also experience Breakup Regret if your breakup was what I call a Reactive Breakup. I sometimes classify breakups into two types: Intentional Breakups and Reactive Breakups.

Intentional Breakups sound like this: “Can we talk? I have been thinking a lot about this and I think it’s time for us to break up.” They are planned. They are initiated by someone who may be upset (because endings are so flipping hard), but not triggered. I suspect that because an Intentional Breakup is mindful and intentional, that sets both parties up for post-breakup healing. I suspect also that Intentional Breakups are more likely to stick, to feel final, to feel decisive.

Reactive Breakups sound like this: “That’s it! I am so effing done!” They are impulsive. They are often initiated by someone who is triggered and/or flooded. I suspect that because a Reactive Breakup happens in the context of a conflict, a Reactive Breakup may set both parties up to struggle emotionally in the aftermath. I also suspect that Reactive Breakups are less likely to stick. That the intensity and suddenness of the ending sets the lead up to feel regretful about what they did. Reactive Breakups prime a couple for experiencing Breakup Regret!

When someone engages in Reactive Breakup Language, or RBL, in the context of a fight, their words reflect a hidden motive, and that’s what we need to better understand. What’s beneath the surface may be:

  • Scenario 1: “I feel deeply misunderstood, and I am desperate for you to understand me. I feel otherwise powerless, so I am turning the volume up.”
  • Scenario 2: “I feel out of control. I am desperate for you to do what I want you to do, so I am going to drop this atomic bomb.”

In Scenario 1, the person speaking may occupy one or more marginalized identities such that they are accustomed to their voice being unheard or devalued. In Scenario 2, the person may occupy one or more privileged identities such that they are accustomed to having power. If you are someone who tends to use RBL, begin to unearth the story that fuels this behavior for you—you may have a skill deficit around self-soothing. Conflict feels wildly triggering for you, likely for very good reasons. Perhaps in your Family of Origin, conflict was frightening, and you were alone with huge feelings. You may have a skill deficit around effective communication, so when you’re upset, you head down some unhealthy paths. 

Reactive Breakups are exhausting for both people. They erode relational trust and emotional safety. The other person likely feels abandoned and helpless in the wake of your escalation. You may end up feeling more unheard because if you’ve threatened it before and not followed through, the other person is likely to tune you out when you say it. But when they tune you out, you end up feeling even more unseen.

What to do instead:

  • Make a commitment to not breaking up while you are upset. Feel proud of yourself when you are upset, and you do not threaten or break up.
  • Take a time out, a bath, a walk.
  • Say “I’m hurting so badly.”
  • Get couples therapy.

(6). I don’t trust myself.

Making the decision to end a relationship is a big deal. It is heavy. In order to stay steady in the wake of a decision like that, you need to be able to believe that you are able to make wise choices for yourself. You need to access a kind of steadiness in the wake of your own grief, as well as potentially your ex’s questioning or upset, as well as the upset or doubt of your family and friends. Your Breakup Regret may reflect that there is a part of you that does not believe you are able to chart your course. 

You may confuse clarity with cruelty. A part of you may struggle to trust and remember your inherent goodness. You might confuse the fact that your ex is hurting with the fact that you are hurtful. The decision to end a relationship is not a mark on your character or a reflection of your worth or goodness. Your responsibility is to initiate the breakup with as much care and gentleness as possible, but that is the outer limit of what you can control. Your Breakup Regret might be a reflection of your struggle to trust yourself.

What to do:

So I have explored six different etiologies or causes of Breakup Regret. If you are currently experiencing Breakup Regret, I hope that this discussion offered you insight. Insight is powerful. When someone offers language or perspective that is right there for you but perhaps not quite in your conscious awareness, it can feel clarifying. Or if something feels conscious for you, then when you hear someone else say it, that can feel like a validation of what you’ve been experiencing. 

But I want to take all of this a step further and talk about what to do about Breakup Regret. Insight without action can feel like you’re spinning your wheels. Here again, your situation is uniquely yours, so not all of these suggestions are going to apply to your situation or even really make sense for you. And the one thing I am not talking about today is starting again with your ex. I’m going to save that for the next set of blog posts. Therefore these strategies are individual strategies, not relationship strategies. Strategies designed to help you cope a bit better with the experience of Breakup Regret versus strategies designed to solve Breakup Regret by undoing the breakup—but know that we will come back soon to discuss the topic of getting back together with your ex.

The big overall what-to-do is to create more capacity inside of yourself to sit with this discomfort. So often we try to fix our feelings with an action. The emotional discomfort feels like confirmation that we’ve made a terrible mistake, and we think that undoing the so-called mistake will rescue us from the uncomfortable feelings. When we try to solve emotional challenges with action we lose the opportunity to grow and learn from our pain. We miss the possibility for initiation. The chance to be led into some deeper wisdom or some expanded capacity. We miss the chance to learn something about ourselves, about the world around us, that would serve us really well in the long run.

The big overall what-to-do is to just go slowly. Breathe into your urgency, quieting it. Put the phone down. Move slowly. Here’s an analogy from the therapy world: one of the things therapists-in-training need to learn is whether and when and how to use self-disclosure in a session with a client. When to share a story or an example from their own life with their client. Self-disclosure can have all kinds of unintended consequences on the relationship, so therapists need to use self-disclosure sparingly and wisely. A rule of thumb that I teach therapists-in-training is this: the stronger the urge you have to share a story about yourself with your client, the more important it is for you to just sit with it. Same thing here. If and when you make the choice to reach out to your ex to explore reconciliation, I want you to reach out from a place that is calm, not urgent, a place that is patient, not pressured, a place that is relaxed, not rushed. Your first order of business is to slow down and find your center.

By the way, slowing down is not just helpful for your journey, it is essential for your ex. If you are the lead, and if you know your ex would get back together with you in a New York minute, you have the added obligation to be responsible, measured, and tempered. You have a responsibility to deal with your Breakup Regret on your own until and unless you are really really sure that you want to reach out and rekindle. There’s a power dynamic between the two of you. As the lead, you hold power. Use it wisely.

Remind yourself that grief does not necessarily indicate a mistake. Grief is a thing unto itself—an understandable thing; a manageable thing. A deeply human thing. Grief stands on its own: separate and apart from any decisions you may need to make.

Take some time to journal about or meditate on this question: To what degree am I missing this person versus struggling with the challenges of single life?

Now you know that memory is subject to change. So make it a practice to notice when you find your mind drifting to romanticized versions of your life with your ex and come back to the present. Immerse yourself in your life today. Savor what is present in your life right now. A 2021 article in the New York Times about our tendency to romanticize the past encouraged people to consider this question: What in my life today I might be nostalgic about down the road? This practice of coming back to this moment will ease your Breakup Regret. It will also put you on more solid ground if you do end up reaching out to your ex down the road. You will be reaching out from a place of gratitude and fullness rather than from a place of desperation and lack.

Another strategy that has to do with mindfulness is to make a practice out of imagining life without them. Allow yourself to fast forward a bit, creating images of your life—full, rich, satisfying—and without them in it. This practice can help combat the pull of Breakup Regret.

An additional strategy, of course, is therapy! Processing your fear that you have made a mistake in ending this relationship is a really valid reason for therapy. Another source of potential support might be your family and/or friends. You might want to process your Breakup Regret with them. Just be careful that they might be confused about how to support you. I want them to resist the urge to tell you what to do—whether that is, “Oh my gosh, if you regret ending it, that’s a sign! Call them up before they move on!” or whether that is, “Are you kidding? Your ex was no good for you anyways. You are better off without them.” Your family’s best move is to just listen and be present. This is hard; it’s hard to resist casting a vote or sharing your hot take. But that’s ultimately what you need the most. What you need most right now is witnessing. They cannot tell you what to do with your life. They don’t know better for you. And if they tell you what to do, and you do it, and it doesn’t go well, you are going to be at risk of blaming them rather than taking responsibility. So ask for the support you need. You could even say, “Listen, I’m having some pretty complicated feelings about my ex. I’d love for you to be a sounding board for me, so I can try to understand what I’m feeling. Do you think you can do that for me?”


We did it! This wraps up our Dealing with Breakup Regret article. I explored potential causes of Breakup Regret and offered you some strategies for dealing with Breakup Regret. I hope you’ve gotten what you needed from this blog post. Thank you for reading!

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