The Break Up 

One of the marks of a true gentleman is how he breaks up with his lover, girlfriend, or mistress, as the case may be. Of course, if the woman in question is a wife, it is not a break up, but a divorce and the same general rules apply, but in a much more complex, legalistically constrained way. But for the purposes of this section, we’ll assume that you’ve been dating and, while the woman is perfectly happy to continue with things as they are, or perhaps to move the relationship up a notch, you are not. Perhaps the initial physical infatuation has ended. Or there are other factors in her personality or behavior that mean you no longer enjoy her company as much as you once did. Perhaps you’ve discovered that all the men in her past have mysteriously disappeared, leaving behind large insurance payments. Or that, all of the sudden, every other sentence she utters contains the word “relationship.” The key is be honest but considerate, especially if the reason is something outside of her control.

If you have been dating any time at all, you have been doing so, hopefully, because you liked the woman – hopefully she is your friend, and, if you handle the break up correctly, she will continue to be your friend in the future. You should not evade or deceive her, which means you should not start dating someone else until you have broken it off with her. You should not break up via email or phone – be a man and do it in person. Make sure you pick a place that you can both leave from immediately as soon as possible once the point is made. As in your other dealings, be calm and straightforward. At the first available and appropriate time, you should tell her that “this is not working out the way I had hoped. We need to make a change”. Do not blame her for whatever problems existed in the relationship; blame yourself to the extent this is true. As a gentleman, your object is to cause as little pain as possible, especially to those you care about. If you have spent a lot of time with someone you don’t care about, it is your own judgment that should be called into question. Do not equivocate – you should be gentle, but firm. Dive into the pool of heartbreak and get it over with; nothing is gained by wading slowly in, except to prolong the pain. If she cries, you must stay as long as the tears are falling, but once they stop, she’ll probably want you gone from her sight quickly.


After the breakup, you should allow a decent interval of time before you attempt to resume the relationship as a friendship, if she is willing to do so. The mark of a mature person is that you can end relationships, be they personal or business, without rancor. If the person had some quality you found attractive, other than sexually, you will hopefully still find that quality in the person as a friend.

All the same rules apply in reverse. If she breaks up with you, then your object is to make the process as painless for both of you as possible. Graciously accept her decision – and the more gracious you are, the more regretful she may be, later, that she had the poor judgment to break up with you. Take the high road, but make it short. In situations like these, the meeting should not be prolonged. Do not argue or protest. Make it clear that you enjoyed her company – and if you want to be especially devious, you might just innocently mention one of the times that she enjoyed most when you were together, but only in the context of acknowledging the good times you had. Do not promise to keep in touch, but tell her that it’s best you spend some time apart for a while before you try to resume a friendship. Since you are a man, you won’t cry at this point, no matter how much pain you may be in, but, in the privacy of your own home, with a drink in hand, the tears may fall, but only in the company of your dog or cat. Once you have broken it off, it’s up to her to initiate any post romantic friendship. If you hope she’ll come to regret her decision – and of course you do – you will make the greatest effort you’ve ever made to be classy at this difficult moment. Under no circumstances will you be accusatory, or plead with her. If the situation is just too much, it’s fine to grab your coat and leave. Far better to beat a hasty retreat than to fight a battle you won’t win. In any event, this is not a situation that should be prolonged; she’s done with you – smile and say goodbye.

As a woman, she’ll want to discuss this sort of thing with her friends. As a man, you won’t. Nothing cures this pain but time. And the next woman.

PS – Don’t try to get her back. Not yet. Too early

PPS – Of course she’s with someone else now, fool. You waited too long.

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