
Believe me, I’ve tried to “heal together” or “stay in touch,” and I’ve hurt more than I needed to and reversed breakups that shouldn’t have been reversed. And that can’t happen if you’re still talking to one another. Whether the reasons are ironclad or evergreen, I think they need to be observed from an emotional distance to be fully understood. When a relationship reaches a breaking point, that means something. Time and space serve an important function. And if I could bold and underline one bit of advice I’ve received, tested, failed at, succeeded at, then passed on myself, it’d be that talking to your ex post-breakup always makes things harder, even if it seems like it might do the opposite. I also believe that deep regret and the intense desire to get back together after a breakup is part of the process, rather than proof of a mistake. Maybe it’s patronizing to say so, but I believe that a lot of people could be in more compatible relationships than the ones they’re in-especially if they spend a lot of time fretting over who they’re with. Since I wrote about ending my longest relationship, a lot of people have asked me similar questions: Did I end up regretting it? Would they regret their breakups, too? My answer is almost always the same: no and probably not. I know the thought of getting over your grief sounds just as upsetting as being in it. I know that advice isn’t overly helpful, though. Or rather, the inevitable healing that will happen within that time. I know that dark place really well and (platitude incoming) the only thing that helped was time. Am I a monster for leaving someone who loves me unconditionally? But on the other hand, my ex-girlfriend wants nothing more than for this to work and I’m afraid I’m making a huge mistake.

My mind says I did…that if we got back together, I would just continue the cycle of going through the motions and being half-bored all the time. I guess I’m wondering…how do I know if I made the right decision in leaving? Did you regret it? Why did you leave? Was it a chemistry issue? A lack of compatibility? I’m in the midst of intense guilty sadness and am questioning whether I made the right call. I recently broke up with my girlfriend of four years, and almost everything you described in this story about leaving a happy relationship, I felt, too. I still get questions all the time about staying in or leaving relationships that feel just left of “right”-and while I more so believe in a shifting set of pros and cons than a divine path forward-I do think most people have a deeper truth hidden somewhere in their guts, layered under a lot of secondary emotions like fear and guilt. I wrote the below advice column in September of 2017, and am re-sharing it today in honor of Mistakes Month.
