Recently I broke up with a guy who was great, but just not “the one.” While there were at least 10 things I wish he would have worked more on, I just knew in this case it was a hopeless cause – it wasn’t like if he fixed or changed those things that we were a match made in heaven. But I cared about him enough to want to tell him, for his sake and for the sake of his future relationships...

Recently I broke up with a guy who was great, but just not “the one.” While there were at least 10 things I wish he would have worked more on, I just knew in this case it was a hopeless cause – it wasn’t like if he fixed or changed those things that we were a match made in heaven. But I cared about him enough to want to tell him, for his sake and for the sake of his future relationships.

Let me provide an example. On our first, second, and third dates, we split the bill. In fact, I think I paid on the third. I’m all for going Dutch, but at the beginning of a courtship, no girl wants to think that a guy is cheap, and every girl wants to feel like they are being wooed and courted. I eventually confronted him about this, asking if he thought it was normal to go Dutch all the time, and he said, “Yes – you go Dutch until you’re married, and then the man pays.” HUH? (I ran this by several friends to confirm I wasn’t crazy – and apparently, this is not the norm). We worked out a solution that worked for us – temporarily. But I don’t think many girls would have given him second and third chances the way that I did, and so after the breakup, I really wanted to warn him of this for the future.

Then I realized something. If I had at least 10 things I could tell him, for sure, he had to have at least 10 things he could tell me. Uh-oh. When relationships don’t work out, in most cases it’s not all one person’s fault. I’m sure I had qualities (or lack thereof), bad habits, or behaviors that he wished he could change. And as much as it would bruise the ego, I guess I’d rather want to know so I could work on those things for the future.

So, remembering a term I learned in the marketing world, I considered asking him to have a breakup “post-mortem” – an honest, sincere discussion about what went wrong, and what each of us could have done better. Businesses do it all the time after big meetings, events, and sales pitches, so why can’t people? Yes, I know. Feelings are involved. But I still wanted to consider the option.

It’s kind of like how everyone knows that K____ has terrible breath, and always has, and it probably lessens her chances of successful relationships – but no one has the nerve to tell her. Don’t you think that if K____ knew she did, indeed, have terrible breath, that she would want to know and do something about it? I sure would.

I laid out the pros and cons of having this kind of a potentially helpful, potentially ego-crushing conversation in order to decide. While the “pros” include that it’s helpful, educational, and ideally sets you both up better for your next relationship, the “cons” include hurt feelings, bruised egos, potential fighting, emotional scarring, and negative feelings for your ex – maybe even ones that weren’t there before.

The solution may be, once the breakup is over and emotions have subsided, to propose the idea to your ex and see what he or she thinks about it. This definitely isn’t something that can or should happen in the heat of the breakup, or even within a few weeks of breaking up (or whatever time limit is appropriate based on how long you dated).

When the time is right, ask for a meeting over coffee, a phone call, or if you can’t bear to hear things in person, an email exchange. Be prepared – your ex may say absolutely not, and you’ll have to just move along. Keep the conversation positive and helpful, providing a compliment along with every piece of constructive criticism. You’ll have to build up your sensitivity walls, because if you can’t take it, don’t dish it out. And never fear, as perfect as you think you may have been in the relationship, there will no doubt be a few stingers to your personality and several things you’ve done wrong. Maintain a mature tone and keep your calm so the conversation doesn’t escalate (again, this is why timing is important – you want to wait until emotions have subsided).

If you and your ex do decide to have this conversation, make sure you are doing it for the right reasons. This is not about getting one last jab or being “right”, and it’s especially not about getting back together. The only purpose for this is to gain useful information for future relationships – with other people.

For me, in the end, I decided that what was done was done, and I didn’t want to hurt this person who I cared about any more than I already had. And if I’m being honest, I also figured that my sensitive ego most likely couldn’t handle what I’d get in return. Yes, I may have learned some things that I could work on in the future, and I probably could have helped him refine his dating skills as well, but I realized that we just weren’t a good match, and (hopefully) there will be people out there who love us for who we are – in which case, we won’t ever need a post-mortem, since there won’t ever be a breakup.

If you were to go through a breakup, would you propose a post-mortem with your ex? What would you tell them? What do you think they’d tell you? Are post-mortems helpful or harmful?