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Understanding the womanizer complex

I have a friend who is an incurable womanizer, something I've come to believe is the underbelly of a much deeper flaw in his character. For six or seven years, he and I have met for cocktails in the afternoon, almost on a daily basis - unless one of us is out of town or otherwise predisposed. He constantly degrades women, using the most vulgar four-letter words to describe those women who don't find his tireless, same-old jokes amusing or don't respond to his crude pick-up lines. Attractive, responsive women become objects of his fantasies, and are often referred to as his "next victim". On those rare occasions that he actually "gets lucky", he can't wait to get back to the bar the next afternoon and tell everybody all about it. I've called him a pig; he considers that a compliment! Other 'regulars' at the bar see him as relentlessly self-absorbed as he flashes cash around, buys rounds of drinks for the house, and boasts about anything from his latest cruise to his investment portfolio. It's like he doesn't even realize how it turns so many people off; if he asks about you, you'll be lucky to get three words out before he turns the conversation back to being all about himself. He is my friend, and there are times when I know he doesn't appreciate my honesty about his salacious behavior.

He's lived with an attractive, pleasant, good-hearted woman for eight years, who - for reasons known only to God - adores this overweight, chain-smoking alcoholic. Between the two of them, they enjoy the "good life" with multiple luxury vacations each years, routine hundred-dollar dinners at the finest restaurants, and all the accouterments money can buy. Both are intensely materialistic, yet both seem strangely confused as to where their life together is headed. There's always talk about marriage, but solid plans never get implemented.

Although I recognize I'm just playing amateur psychologist, I believe I know why my friend behaves as he does. He is perhaps the most insecure person I've ever known. Shortly after his first marriage, he came home to find his wife in bed with another man. While he casually walked away and never looked back, I suspect that bruised his massive ego more than even he knows.
His second wife, apparently, was not the wonderful woman he thought he married. While I'm sure he ignored his own flaws, he seems to magnify all of her shortcomings. Now, this third major relationship in his life probably scares him to death. His 'significant other' has been married


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