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Why do all the smart, pretty women end up with jerks? Dear Jon has the answer.

by Dear Jon
January 8, 2001

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Fourteenth Sort_Dear Jon-Why do all the smart, pretty women end up with jerks? Dear Jon has the answer. ACTUAL LETTER TO DEAR JON

Dear Jon, Will the Vikings win the Super Bowl? Unsigned.

Dear Unsigned,

Hahahahahoohoohoohoohoohehehehehehe! Whew.


Only someone from Minnesota would ask that question. It is like asking whether Mondale would make a good President.

If we have a replay of Vikings vs. Raiders, the outcome will be the same. You might be too young to recall when the Vikings played the Raiders; it was the FOURTH LOSS for the Vikings in as many Super Bowl appearances. One might say they will get the monkey off their back just like Denver did, but that ignores the simple fact that when Denver beat Green Bay, Denver had played all season like a team of destiny. The Vikings skidded into the play-offs on a three-game losing streak. No one in the NFC has played like a team of destiny, but it looks to me as though Raider Ball has come back to Oakland. And anyway, the Vikings have to get past the Giants, who have the home field precisely because of the Vikings slide, and the Giants look awfully tough on defense.

Dear Jon,

Why do all the smart, pretty women end up with jerks? Sincerely, A Lonely Nice Guy.

Dear Ly,

You ask a very complicated question. Since I am married to a smart, pretty woman, I don’t know exactly what you’re saying. But I will take this opportunity to share my opinion about how smart, pretty women choose their men, and maybe that will help you.

First of all, we should define “smart” and “pretty.” I know that I am a smart person. I am the standard of smartness, so that people who are as smart as I am are smart, and those who are smarter than me are REALLY smart. It just so happens that most of my friends and my wife are REALLY smart. So, when you meet someone, ask yourself, “Is this person as smart as Dear Jon?” Then you will know.

Second, we should define “pretty.” Frankly, someone who signs their letter “Lonely Nice Guy” is feeling sorry for himself, and does not realize that he probably still carries around the unrealistic standards of beauty he had as a thirteen year-old, when he was influenced by paging through the Women’s Underwear section of the Sears Catalogue. Not that I would know anything about that. But let me just say that the Sears Catalogue was an American Institution, and that the decision by Sears to discontinue catalogue publication just shows how far this nation has fallen from the greatness it knew when I was an adolescent.

In any event, where “pretty” can become synonymous with “attractive,” it becomes clear that the Underwear Model standard is not only unrealistic, but severely limiting. The fact is, a woman who smiles, who looks you in the eye, who has stories to tell but likes to listen to others, and who respects others by taking care of the way she dresses, smells, and combs her hair, is an attractive woman and can be thought of as “pretty.” All those things are true for men, too, by the way.

So now we come to the complicated question: Why do so many women who have a lot going for them end up with jerks who have no idea how lucky they are?

To paraphrase some current psycho-babble, some women do become “jerk” magnets. Basically, these are smart, pretty women who, while perfectly sober, are attracted to the unemployed tattooed chain-smoker on his fourth beer who is swearing at the dart board. The smart, pretty woman is convinced that THIS time, she will be able to change THIS unemployed tattooed beer-swiller by loving him enough. By now twice-divorced, she believes, despite the unanimous opinions of her therapist, her mother, and all her friends, that the divorces were HER fault for not loving her first two beer-swilling husbands enough.

This smart, pretty woman normally has three kind, sensitive men in her life, who are in unanimous agreement with her mother and all her friends about the jerks that she marries. One of them is a homosexual and another one is married. She feels fondly for the unmarried straight bachelor who always remembers her birthday and has something funny to say and offers his shoulder to cry on, but because she met him at church during a religious phase following her first divorce, she can’t believe that he is “husband” material, because deep down she believes one of two things, and possibly both: 1) Men are projects for women to work on, so the more a man needs to change to become a decent human being, the more she will fall in love with him; 2) She does not deserve to marry a man who treats her well, and only deserves the kind of husbands she can find in clubs that paste the Confederate Battle Flag in their windows.

Now, Mr. Lonely Nice Guy, you might be the person who finally liberates this smart, pretty Underwear Model from her destructive life-pattern. Or, you might realize that there are plenty of smart, pretty women when you choose to notice them. You will see that many single women dress nice and smell nice, smile and laugh, look you in the eye, have a life-story and are genuine enough to hear yours, too. Many of these women would like to meet unmarried straight bachelors who smell nice and dress nice and open doors for them and laugh at things that are funny. Good luck. And stop feeling sorry for yourself. Smart, pretty women really don’t dig that.

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