Regretting a Breakup: Finding the Truth Within

I penned the following advice column back in September 2017, and I’m sharing it again today as we celebrate Mistakes Month. Countless individuals still reach out to me, grappling with the decision to stay in or leave relationships that just don’t feel right. While I believe that navigating relationships is more about weighing pros and cons than waiting for a divine signal, I do think that most of us have an inner truth buried beneath layers of fear and guilt. The challenge lies in unearthing it. Here, two of us embark on a quest for answers.

Questioning the Decision

Dear MR,

Recently, I ended a four-year relationship, and I resonated with everything you mentioned about leaving a happy partnership. Now I’m left wondering if I made the right choice. Did you ever regret your decision? Why did you leave? Were there compatibility or chemistry issues? I’m consumed by guilt and sadness, and I’m doubting my judgment. My mind tells me I made the right call, that getting back together would only mean going through the motions and feeling half-bored all the time. However, my ex-girlfriend desperately wants us to work things out, and I fear that I’m making a colossal mistake. Does leaving someone who loves me unconditionally make me a monster?

Thank you.

First and foremost, I’m sorry to hear about your heartbreak. I understand that dark place all too well, and I can assure you that time is a powerful healer. I know this may not provide immediate comfort, but healing will inevitably come with time. I’ve been there before.

Since I shared my experience of ending my longest relationship, many people have asked whether I regretted it and if they would regret their own breakups. My response is almost always the same: no, and probably not. Perhaps it sounds condescending, but I genuinely believe that many people could find themselves in more compatible relationships than the ones they are in, especially if they spend a significant amount of time contemplating their partners. Deep regret and a strong desire to reunite after a breakup are part of the healing process, rather than evidence of a mistake. And if there’s one piece of advice I’ve received, tested, failed, succeeded, and shared with others, it’s this: talking to your ex after a breakup only makes things harder, even if it may seem otherwise.

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Time and space play crucial roles. When a relationship reaches a breaking point, it signifies something. Regardless of whether the reasons are clear-cut or deeply ingrained, I believe they must be observed from an emotional distance to be fully comprehended. And that can’t happen if you’re still in constant communication. Trust me, I’ve attempted to “heal together” or “stay in touch,” only to suffer more than necessary and undo breakups that shouldn’t have been undone. In the moment, everything seemed reasonable and level-headed (after all, we’re adults and we still care about each other, right?), but it was self-sabotage, without a doubt. Even if breaking up seems ridiculous in the midst of grief, I don’t believe that two people can help each other or reconcile healthily under such circumstances. The temptation for pain relief is too great, and no one is thinking clearly.

Six Minute Dates

Of course, this is based on my personal experience and observations, and while there are exceptions to every rule, avoiding communication and taking time to heal are cliches for a reason. They are more complex than one might expect.

Seeking Something Different

To address your question, I ended my relationship due to a lack of compatibility. We shared wonderful moments, and we could have continued as we were, but deep down, I knew that certain elements were missing. No matter how hard I tried, I couldn’t suppress the desire for those missing pieces (a truth I ignored for years). Ultimately, my longing for something more prevailed over my desire to stay. I struggled with this decision internally, but I can now confidently say that it was a reasonable longing. I wasn’t merely bored, nor was I searching for a fairytale romance—I simply sought something different.

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And it’s crucial to remember: it’s perfectly acceptable to want something different! This is your life, after all!

Following the breakup, I was devastated. For weeks, I convinced myself that we would reunite, but I took no action. Two months later, I convinced myself that I was ready to reconnect, but I remained silent. Ultimately, I stayed strong and, as expected, these thoughts were merely manifestations of my grief. Now, a year and a half later, I am at peace with my decision.

My parents, who have a strong and lasting marriage despite their differences, have always believed that lasting relationships are built on kindness, not a perfect match. I held this belief close to my heart, and their marriage made it challenging for me to leave a “kind” relationship in search of a “better match.” However, while I still hope to embody their approach one day, I’ve come to appreciate that their perspective belongs to a different era. They never agonized over their commitment, and they could never truly understand the magnitude of my struggle.

Egg timer

It seems that many of us today feel at odds with previous generations in this regard. Despite the criticism we face for our obsession with choice, having more options isn’t inherently negative. It does, however, present its own challenges—challenges with which I am willing to grapple in exchange for the freedom to steer my own course, rather than merely drifting along the current of societal expectations. While the pursuit of a perfect match may be futile, some people are undeniably more compatible than others. This spectrum exists and is not a binary concept—I have experienced its magic firsthand. If long-term monogamy is your goal, it’s perfectly acceptable to place greater importance on choosing the right partner from the outset, even if kindness alone could potentially sustain a relationship.

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We must all adjust our expectations in various aspects of our lives—that’s an enduring challenge we face. However, while there are countless hopeless romantics who need to be reminded that love isn’t a fairytale, I believe that there are just as many logical worriers who need reassurance that relationships aren’t meant to be traps, and that settling for a “good-enough marriage” is its own kind of fairytale. Which of these two are you? Perhaps I am presuming, but something tells me that you lean toward the latter.

You are not a monster for desiring something different. What you did was save yourself from a relationship you knew would continue to leave you unfulfilled. You listened to your gut, despite your fear. And if you reread your own question, you will find that you acknowledged this truth yourself. In making this decision, you also saved someone you genuinely care about from investing in a relationship where her partner’s heart wasn’t fully committed. Ultimately, your decision was an act of kindness towards both yourself and her.

Photo by Flashpop/Smashed egg timer via Getty Images.

Ask MR Identity by Madeline Montoya.