Verified by 
There is that great old Paul Simon song, 50 Ways to Leave Your Lover. There’s probably even more ways than that that Paul didn’t imagine, but we all know the basic relationship-ending genres: the calm but often painful let’s-be-friends conversation; the dramatic emotional meltdown complete with screams and sobs; the fade-away often seen in high school sweethearts who go off to college or those couples who realize it’s just too difficult to keep up a long-distance relationship; the abrupt, we’re-done, hot or cold endings common with the uncovering of an affair or other secret mischief. Some endings are mutual; more often they are unbalanced with one partner more determined than the other to call it quits; some are horribly unbalanced with the rejected, devastated partner is unable to accept the reality and let go.
But regardless of how the ending ends, what often remains for many is regret. Over the years I’ve heard many stories of relationship regrets and basically they take the shape of three overlapping sources.
Regrets over the ending itself
Here is where emotional meltdown led to saying things the person really didn’t mean or didn’t mean to say, or where the argument was too angry or hurtful, or the ending was just too abrupt. While the person may be steadfast in realizing that she needed to end the relationship, her regret is that it did go down the way she imagined. Often there was little follow-up and, as a result, the person feels haunted.
What to do:
Here it’s about apologies, not for ending, but for the drama and emotion and hurtful comments. Here you step up and do the emotional mopping up that you didn’t, for whatever reason, do at the time. You make the call and leave a message, send an email, text. You make clear that you are not trying to start up again, but instead just wanting to apologize for how it all unfolded.
Here you also forgive yourself. Everyone does the best she can at time, and you can always look at the past through the new filter of the present. It’s a lesson learned, but not a reason to be haunted and regretful or to continue to punish yourself.
Regrets over lack of closure
This is often a close relative of the bad ending, but the core of this regret is that you have nagging questions that are unanswered, that you didn’t get a chance to fully get things off your chest and help the other person understand how you felt and what was behind it all, or most often, a combination of both.
What to do:
Like the other, it’s time to step up and speak up if possible. Here, for example, you write, six months after you found out about the affair and ended the relationship, an email, or instead of the superficial chit-chat texts, have a serious face-to-face conversation with your old high school girlfriend. You say all that you wished you had said, or pose all the questions you didn’t get to ask.
Again, be clear about the purpose—namely, to not start up the relationship again, not to circle back and castigate the other because you’re still angry, but to help connect the dots that made up the relationship in your mind, and hopefully, finally, put it to emotionally and mentally to rest. You talk about you, you talk about soft emotions, you talk about what you appreciated, as well as what might have gone wrong.
And if reaching out is not an option because you don’t know where the person is, or because he said he never wants to talk to you again, or simply because you lack the courage, then write a letter that you will never mail. Address it to the person, and write down what you wish you could say if you were to see him or her one time for one hour. Write to get everything in your mind and heart out. Then, write another letter back addressed to you from the other, this time saying all you wish the other would ideally say back.
Do them back-to-back and take your time; this can be emotionally powerful but healing.
Regrets over not trying hard enough
These are those haunting regrets that you maybe should have not quit when you did; that you didn’t, and maybe should have, given the person another chance; that you didn’t push yourself up that hill just more time.
What to do:
These regrets generally are stirred in two different ways. Sometimes they come much later—two years after the breakup, you find your mind and emotions drifting back to the relationship and feel that sting of regret that maybe, just maybe, you should have given it one more try.
While this may indicate a lack of closure, the fact that these regrets surface relatively suddenly and unexpectedly suggests that it probably has less to do with that relationship and more to do with where you are in your life right now. I find myself often saying to couples on the verge of getting divorced that two years from now they are likely to have days when they feel good about their decision to divorce and other days when they think they never should have left.
The difference comes from viewing life through the lens of the present. We are continually recreating our pasts because we continuously look back colored by our current and changing emotional states. If our lives are going well, the process of cognitive-dissonance makes our past decisions match our positive state—the breakup was a good decision. If, unfortunately, we are struggling in our lives for whatever reason two years later, we now look back and understandably wonder if we made the right choice, wonder whether we would be in a better place now if we hadn’t taken that path.
If you are questioning and regretting your decision suddenly now after a longer period of time, look at your present life. Your regret is likely a symptom of something that you need to work on and improve right now.
On the other hand, if your regret has never gone away or is more recent—lingering within weeks or months of a breakup—where you are having second thoughts, where you wonder whether you were too impulsive, where, after your fury of the affair dies down, you realize that there was something strong and important in the relationship that maybe shouldn’t be thrown away, step back and decide on what you do and don’t want to do.
But before you do, ask yourself this difficult but important question: Do you really want to make the effort to give it another shot because you care about the other and the relationship, or is there a danger that you are falling into default mode? Are you possibly being driven because you are actually fearful about the future and finding another relationship, and so are drifting back, albeit with mixed feelings, to the old one? If you sense you are drifting because of fear or loneliness, you may want to stay planted where you are and look ahead as best you can.
But if you decide in your heart that yes, you do need to give it one more try to see if it can work, or to be able to really leave without regrets, then go for it if the door of opportunity is still open. If you do, decide in advance your own criteria for change—what is it that you and the other concretely need to do differently. Then set a timeframe to work on the changes.
The reason for this is that it is all too easy to “work on it” and quickly and simply to fall back into old patterns—to be “nicer” for three weeks, then sink into the mixed feelings you had before you left—always hoping that it would get better even though no one is really making an effort to make it so. You need and want to work against going on autopilot. Knowing exactly what you both are trying to achieve can help you stay on track. Once that is clear, just put your head down and focus on you and your side of the relationship.
And when you reach the end of the timeframe—say three or six months—lift your head up and see if things are truly on a better path. If not, you can hopefully walk away feeling that you truly did give it your best effort.
And now...
Finally, if you are thinking of possibly ending a relationship in the near future, you may want to try and incorporate some of these ideas into your thinking. Endings are painful because grief is painful, and the endings of all relationships, regardless of the circumstances and quality, are at their base about grief. Regrets add to this challenge, adding emotional baggage and doubts that can weigh you down and stall the already painful grieving process.
Decide now what you need to do most to leave without regret.
