How Do I Break Someone’s Heart Without Feeling Like An Asshole?

There’s nothing more painful than knowing you have to break
someone’s heart.

Whether it’s the end of a relationship, the termination of
an employee, the delivery of a verdict, the cutting of a player, the dismissing
of a volunteer, the rejection of a candidate, the reporting of a diagnosis or
the conveyance of bad news, at some point in life, we all have to put on a pair
of heartbreaker’s shoes.

I’ve done it a few times before. Both right and wrong, both
coldly and compassionately, both personally and professionally. And I learned
that I could insure myself from the devastating guilt and self-torture that
accompanies the process of severance if I asked (and kept asking) one question:

How will I need to
feel when this is done to still be okay with myself?

That’s the filter. That’s what I need to answer before
delivering the death stroke.

Otherwise it will be very hard to sleep that night.

Years ago, I reached a point in a relationship where I knew
I had to end it. I couldn’t take it any longer. My stomach was tied in knots,
and I knew that if I waited another day, terrible things would happen. Plus the dog was seriously onto me.

And in the eleventh hour, I remember sitting in my car, clutching
the wheel like a life preserver, refusing to go upstairs and end my broken
relationship. At that point, no matter what I said, it would break her
heart. No matter what I said, she would hate me for it. And there was nothing I
could do to change that.

But I also knew that I could live with myself if I communicated
in a way that was kind, honest and clear. Those were my parameters. Kind, honest and clear. Do that, and you’re not an asshole.

Ten minutes later, I dragged myself out of the garage,
walked upstairs, took a few deep breaths and dropped the biggest bomb of my
life. I told her it was over.

Then she vomited for twenty minutes.

It was the lowest moment of my life. Sitting on the floor of
the bathroom, rubbing her shoulder, pretending to cry, wondering how long I was
supposed to fake it until she took the dog and walked out the door. Horrible, horrible.

But there was nothing left to say. The bomb had dropped, the
bell had rung and the relationship was dead.

As soon as her car was out of sight, I immediately called my
best friend and said, “I need you to tell me that I’m not an asshole.”

You’re not, he

I thanked him, hung up and passed out.

Slept like a log that night. Ten straight hours. No dreams.

And when I woke up, part of me wondered if I should have
felt more devastated, more disturbed, busy counting dots on the ceiling,
tossing and turning until the sun came up.

But then I remembered the promise I made to myself: Kind,
honest and clear.
That’s how I needed to feel when this was done to still be
okay with myself. And I did. I made the right decision.

The point is, the only person you’re truly with forever is
yourself. And if you can’t go to sleep feeling content with that person, you’re
in trouble.

If you have to break someone’s heart, ask yourself how you need to feel when it’s over to still be okay with yourself.


Whose heart do you need to break?


Ask yourself,”How will I need to
feel when this is done to still be okay with myself?” and then go do it.

* * * *

Scott Ginsberg

That Guy with the Nametag

Writing, Publishing, Performing, Consulting

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