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Sharing 25 Years of Dating Wisdom

by The Unknown Don

A few days ago I turned 40 and tonight I was just thinking about past relationships... the things that went right, the things that went wrong, and the outright disasters.

A little background. I'm a reasonably well-off, college-educated white male, 6'0" in good shape. I've been married once for 5 years, divorced for 3. I went through my AFC (wussy) phase in my late teens, but I was fortunate enough to snap out of it by the time I was 20. From then on it was smooth sailing.

I've been reading many of the articles and message threads here. I agree with quite a bit, but I think there are some areas that need a little fleshing out and amplification. So I'd like to share some of my observations in no particular order:

1) No matter how good-looking a woman is, she will always become boring (particularly sexually) with time. The boredom accelerates if the relationship becomes domestic (living together, marriage, etc.).

2) Men remain in boring relationships out of sentimentality or financial convenience... but rarely fear.

3) Over the long run, the periods that men are without a partner and frustrated are generally happier than being stuck in a relationship which has lost its luster.

4) Women generally do the selecting in the earliest phases of a relationship. Once a woman has committed herself emotionally, the balance of power shifts to the man (assuming he has some degree of self-confidence).

5) Contrary to the myth that "looks don't matter" to women, physical attraction may be the primary and key deciding factor for a woman. However, it is difficult to determine just what will be physically attractive to any particular female. Even though men also value looks, they are far more willing to initially compromise on looks in the pursuit of sex.

6) If a woman is initially physically attracted to a man, there is very little he can do wrong on a first date.

7) If a woman is not initially physically attracted to a man, there is very little he can do right on a first date.

8) Always pay attention to a woman's actions. If she says she likes you but will not respond to kissing or touching, then she doesn't like you. Move on immediately.

9) Just like there are many men who are simply assholes, the same goes for women. If a woman is rude or inconsiderate in the first few dates, move on immediately -- it will not get better with time.

10) Any strange psychological problems, drug problems or baggage... move on immediately -- it will not get better with time.

11) All women have the same body parts. Don't obsess over one particular female based on appearance. It's a waste of life.

12) The vast majority of men get rejected much more often than they seal the deal. If you are rejected you are simply shooting par. Relax.

13) Above all, women crave attention. Women want to date rock stars not because they find the man himself exciting, but because they find the thought of sharing the limelight exciting. Ask any young girl what she wants to be. Top answers: model, actress, singer.

14) The sad truth is that we can only truly know ourselves. A wonderful woman you marry today and trust completely may change radically over the course of time to become your most vicious enemy. There is absolutely no way to predict this or stop this from happening. It is, ultimately, a matter of chance.

15) There are far more available women out there than you think.

16) Humans are generally not very good at monogamy. Most men in long-term relationships cheat to varying degrees, and a great number of women do as well. It's simply a matter of biology. If you discover that your significant other had an affair, the best course of action may sometimes be to take the high road and let it go.

17) Never, never, never be afraid to approach a female. To reiterate: they all have the same body parts, and they are all composed of Carbon, Hydrogen, Oxygen, Nitrogen, and trace elements. There isn't a single woman on Earth who is "above" you, no matter what her affectations and social pretenses.

18) Women tend to be far more pragmatic about relationships than men.

19) Unconditional love is a nice sentiment, but does not generally apply to male/female relationships. It does however, almost always apply to female/child, and to a slightly lesser extent, male/child relationships.

20) Never become financially entangled with a female. If you decide to marry, do not even think of doing so without a prenuptial agreement. This is common practice in Europe, however there is still a social stigma attached to these agreements in the U.S.

21) Sex is generally overrated. The amount of effort expended in obtaining it vs. the payoff is absurd.

22) If a woman in a relationship begins to lose interest, it is usually impossible to regain it. The feelings you are having of confusion and fear mean something... trust your gut and move on immediately.

23) After breakups, men usually tend to forget about the sexual boredom and once again find their past girlfriends exciting.

24) If a woman has not gained some form of emotional stability by the time she is her mid-twenties, then it is too late. Move on immediately.

25) Avoid women with a large number of pets or women who pay unusual amounts of attention to their pets.

26) Most first-time marriages fail. Consider that if you decide to get married, there is better than a coin-flip chance that you will be divorced. If any other civil contract had as high a failure rate, Congress would outlaw it. The world has changed dramatically in the last three or four decades and many people have postponed marriage until much later in life, or simply never get married.

27) If you do decide to get married, remember that it IS a contract - one that you can't get out of without a great deal of expense and pain. Never be sentimental about marriage. Love is only one piece of the pie. You may love a woman terribly, but you may also be unable to deal with her in everyday affairs and money matters.

28) Avoid women with addictions, particularly the big three: nicotine, alcohol, and born-again Christianity.

29) Never avoid discussing something that bothers you out of fear of losing the relationship. Most relationships will - sooner or later - be lost anyway. It's better to stand up for yourself early on.

30) Always keep the ego in check. If a woman you are approaching for the first time is rude or obnoxious, simply go away. Tossing an insult or scathingly witty comment back simply demonstrates that your self-confidence is far lower than hers. Always, always, always take the higher road. This doesn't mean be a pushover, it means you bend with the wind (kind of a Zen thing). The best way to disarm an obnoxious female is to treat her with courtesy and respect.

31) There is an inverse relationship between self-confidence and concern with what others think of you.

32) Self-confident men desire sex, but don't dwell on it.

33) Most reasonable, normal women will make it clear if they are attracted to you or not very early on. Period. If you have difficulty reading a woman's motives, or find yourself dwelling on what she meant by something she said, or you can't seem to pin down a date, then move on immediately.

Hope this helps.