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DEAR JON LETTERS
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Should a lonely woman hold out for the Real Thing?

by Dear Jon
September 30, 2008

ACTUAL LETTER TO DEAR JON:

Dear Jon,

Do I stay with my boyfriend of 5 years, who I'm not madly in love with, or do I hold out for the real thing? Is there such a thing for someone my age or should I be happy with what I have? My boyfriend is a great guy and companion when I get to see him but the truth is, he is often unavailable because of his young children, baseball, golf, bowling, etc. You get the picture. I'm 52, divorced and my kids are older than his. In fairness to him I have to let you know that he was extremely patient with me and my children when we were going through tough times. Not many guys would have put up with what he put up with. He really deserves to be with someone who's crazy about him - and his kids. Meanwhile, what about me?

Lonely

Dear Lonely,

First of all, this is a great letter.

At first glance there seems to be no way I can milk it for comic potential and still leave you, Lonely, with the feeling that writing to Dear Jon was worthwhile. (Anybody can be cheap and mean for laughs. But Dear Jon hasn't been cheap and mean since 2003, at least not consistently. A letter like this one doesn't deserve an answer that is either cheap or mean.)

Second, whether I am being serious or funny, I might come off a bit grumpy. Grumpy does not equal mean. If you are not sure where I am coming from, my portrait appears on the cover of my book, The Dear Jon Letters: Tips on Dating and Mating. I appear as a hairy grown man Cupid, and my romance delivery system is a shot-gun with heart-shaped double-barrels.

So be prepared, because I am taking aim and blasting away.

Barrel Number One: A Woman's Self-esteem

You do not strike me as the kind of person who mopes around feeling sorry for yourself. You are, however, fitting a particular "stereotype" which is that you are a female with low self-esteem. This is not my intuition. Guys do not have intuition. This is based on the data of your letter. Your boyfriend is emotionally unavailable to you, you are bored with him, and yet, because he is a "great guy" you feel like you don't deserve him, that you did not deserve the help he was to you during a rough time, and that he "really deserves" something better than what you can give.

BANG! Get over that. A. Boyfriends are supposed to be patient and help their girlfriends through tough situations. B. Over the course of five years he has become less available to you, and that is the issue. C. When you signed your letter "Lonely" you answered your own question. If you have a boyfriend and you are lonely it is because your boy is not really being a true friend anymore.

You are not wrong to feel that way. You are not to blame. This is not your fault. Go to a mirror and read those three statements out loud 50 times.

Let me tell you the score. This "great guy" has been stringing you along for five years. This is my testosterone talking now--the guy sounds like a jerk to me. Facts: There is no rock on your finger, no commitment, no plans for the future. After five years if your boyfriend is not ready to marry you, then he likely agrees with you about the state of the relationship. It may be that he retreats into his children's sports as a way of avoiding both you and the hard questions about the relationship. The break will not end his world.

Okay. I'm sorry for calling him a jerk. You're right, he's a great guy, and the point is you need to break up with him. Let's move on.

Barrel Number Two: Do You Got it Going On? (Like "Stacey's Mom" from some pop hit a few years ago that I don't have time to look up.)

The real question you are asking is, can you risk breaking up and then not have someone in your life to call a boyfriend, at the age of 52? This is the other side of the "hold out for the real thing?" question, because the risk is that the "real thing" will not materialize anytime soon.

If your self-esteem hangs on being in a relationship, you may need some time to develop some confidence in yourself as an independent woman. Getting some counseling wouldn't hurt the process of finding yourself.

And yet, you are 52. There is a certain urgency that you are expressing, which would have to do with your attractiveness. You wonder how much time you really have.

Bang! How you look is not as important as where you look.

Women who like to have boyfriends will tend to have what it takes to attract men for a long time. Thus it is not uncommon that women in their fifties still "got it going on," if they had it going on in their twenties. So, don't worry about the time issue. There are plenty of single or previously married men in the 47-60 age range whom you will attract as soon as you care to, and probably sooner than that. Thanks to the miracles of modern medicine as experienced by Bob Dole and others, you could even go the "trophy wife" route with a widowed man in his seventies (or older? But then you have to weigh in the "ew!" factor for yourself).

You are probably fine. (I mean fine. Dig it?) So the issue is not how you look, it is where you look. Be careful of your venues.

First of all, the "real thing" never ever involves a man married to someone else. Never ever. Some other situations to avoid: The Biker Honky-Tonk will have you gain the attention of rugged, adventuresome types who will interest you because they will be exactly unlike the Soccer Dad you are breaking up with. Don't go there. I also suggest not wasting your time with radio station promotions for singles, internet dating services, and anything that resembles the "club" scene.

Instead, try describing what you are looking for to good, reliable friends of yours and leave yourself open to a fix-up. I am not saying you should go for anything stupid like a blind date; I suggest more like an introduction at a good friend's cocktail party. In my experience, that kind of situation is where and how the "real thing" gets discovered and the magic happens.

If you cannot trust the judgment of your friends, try connecting to a Mega-Church with "Singles" Ministry, "Divorce Recovery" groups and an active social calendar.

About the Author:
Dear Jon knows several women in their fifties who "got it going on," and is pretty sure his wife won't put him in the dog house for saying so.


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