Dating: Letting a Lady Go – Constructively


When a relationship is over, any man can end it quickly. Depending on the man and his character, it can be done over dinner or over the phone — in a letter or in a few words. Like the song says, “Slip out the back, Jack…Make a new plan, Stan…” You get the idea.

Sadly such breakups can be ugly, spiteful and even potentially dangerous. They certainly descend into open, petty hostility easily enough. But, I caught wind of a real life story in which a man who shall remain anonymous managed to break it off with the lady he was seeing, while also making an attempt to educate her and improve her character.

I was discussing the wayward ways of women with dating expert Eric Rogell when we kicked around the story of a New York gentleman who was dating a younger woman. Rogell and I are each acquainted with this fellow — a long distance buddy with me in Los Angeles and the Midwest and Rogell ensconced in south Florida.

We can confirm that the male in question is in his mid 30s, and the lady in her mid 20s. I’ve also seen the woman in question. She’s a NYC model and gorgeous enough to make the age reach worthwhile. The man was hoping she was an old soul under that perfectly sculpted physique and tailored clothes. The woman was tired of guys her own age chasing her like starving puppies without much to offer by way of life experience once they caught up to her.

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Evidently, the early stages of the relationship went well enough, but matters soon deteriorated. The woman proved every bit as immature as her age indicated, resulting in tantrums and hostility if she didn’t get her way when she wished. The man tried to smooth out those rough edges without returning the temper, but the tension wore the relationship out for him. Exterior beauty only rolls so far for so long, and the wheels came off this situation when the lady chose unpleasantness as her carrot and stick method to snag what she wanted. The man didn’t expect a woman to be meek and subservient, or so I’m told. He would find that boring. But he also dismissed the princess routine. He wanted a more mature equal in his life.

But, what does he do? It was over. He could try to end it quickly. He could try to explain himself. In both cases, he felt sure the business would descend into name calling. He decided he’d explain his decision while trying to outline how the woman could find what she was looking for more effectively in the future.

After a particularly nasty exchange one evening, he wrote her a letter. This is what was forwarded to Eric and me:

My goodness, young lady. Such a temper. I was only making conversation. Genuinely tough people play it cooler than that.

If I’m going to come to NYC, swing through the best hotels, eat out at the newest restaurants, etc., I want companionship that’s adult, educated and sure to enjoy it with some class and good humor. Class is more than a short dress and the right hair.

If you want to date the kind of men you describe — 35+, worldly, experienced, self confident — you’d best learn that we’ve lived and know life is too short to burn time with moody, juvenile girls who have yet to learn to act with mutual politeness. It makes for cold and miserable nights out for us.

You want us? You want us to treat you with respect? You must learn your manners and do the same. We want to date our equals, not spend an evening lost in spoiled child care. You might be a genuinely good young woman. I hope so. Your inside might match your veneer. But you didn’t present yourself that way. Perhaps you have your reasons, but it’s sad. I attempt to put my best self forward in a relationship. You didn’t do the same here. At least, I sincerely hope you didn’t.

So, go brood at the bar. Hit all the clubs and parties. Let the boys buy you drinks and chase you all you like. They’re clumsy, boring and predictable — and you know it. The men those boys want to be — the men you say you want — will be out with women, waiting for girls to grow up and carry themselves with some decency and grace.

Did he let her down easy? No. There’s quite a wallop there. But, he didn’t use pejoratives, either. No name calling. He made it clear he was judging her for his own benefit on her behavior, and not her looks or her intelligence — what she did and not who she was. There isn’t much she can come back with here because she’s been exposed.

Best of all, rather than express some desire for her to drop dead or blow away, the guy challenged her to improve in the hope that she might find what she wanted. It’s a classy move going out the door, and an effort he didn’t have to make.