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One used to hear horror stories about people ending relationships with a brief note. Imagine opening a letter in a familiar handwriting (remember those days?) that you hope will be a love note or an invitation to something fun and finding a “Dear John (or Jane)” letter ending it all instead. Today, that seems almost gracious—compared to being dumped via an email or worse, a text message. Depending on which surveys you read and believe, anywhere from 10 to 17 percent of people have had the experience of being dumped electronically by a sweetheart (or an employer).

For years I have referred to the too-common practice of simply no longer responding to calls (or emails) from someone you’ve been dating, or no longer initiating them, as "the coward’s kiss-off." One avoids the painful “it’s not you, it’s me” conversation by just fading off into the wild blue yonder without actually saying a thing. Does someone who does that think the other person won’t notice his or her absence? Do they think, “If I don’t answer my phone or messages maybe she (or he) will just think I moved and forget I ever existed"? Wrong! What the other person will think is that you are the worst kind of creep or coward. What they will feel is angry, bewildered, used, and demeaned.

Of course, being told to your face that someone wants out of a relationship—whether it's a friendship, a romantic relationship, or a work arrangement—is also likely to hurt, but you do get the chance to hear their reasons and even to say a decent goodbye. Any relationship worthy of that name deserves a decent burial.

Some people, fearful of emotional scenes, arrange a difficult “this is goodbye” discussion in a public place, assuming the other person will exercise more control if others are watching. This may work, and it may not. Over the years, I've personally watched with fascination more than a dozen such public break-ups, with and without tears and loud recriminations.

So is there a best way to tell another person, “This relationship is just not working for me”? And best for whom—the one who is ending the relationship or the one being, for lack of a better word, dumped?

In either role, I strongly prefer a face-to-face discussion. If I am being dumped I want to at least see that this is causing the person ending the relationship some pain and discomfort, that it is not being done casually or on a whim, and that they have the courage and good grace to face me. If I am the one ending things, I feel I owe the other person the same respect, no matter how disagreeable the conversation is.

I can recommend a few things:

  1. Be ready. Before you end a relationship of any sort, whether it's with an employee, someone you dated a few times, or a long-term partner, give the matter some consideration and have some thought-out points to make, such as “I don’t see this going anywhere,” or, “Much as I like you, I don’t think we have the same goal in mind.”
  2. Pick your spot. Choose a time and place where you can have some time and privacy, but if you're convinced you'll need it, go ahead and arrange for a setting where it’s unlikely the other person will be able to make a scene.
  3. Be kind. Say some good things about the person and what you have enjoyed about your time together, as a way of helping them salvage their self-respect.
  4. Avoid an argument. If the other person disputes your points, remain firm. Apologize for hurting his or her feelings, be clear that your mind is made up, and then leave after making whatever arrangements are necessary, such as picking up possessions.
  5. If you just don’t have the courage to do this face to face, or truly believe it would be a bad (or dangerous) idea to do so, then write a letter, but not a text or email—a real pen-on-paper letter. Again, pay some compliments, detail what was good about the relationship, and explain why you feel it needs to end.

NOTE: If you are the one being “fired," it’s perfectly okay to ask for some reasons, so you can learn from an unhappy situation. You may not get the "real” reason, but you may get some information you can use next time around or to offer some balm to your pride.

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