Wanted: Experienced Woman of 40

When you're 30 and can't get women your age to give you the time of day, it's time to open up the field.

By Garrison Keillor
Published August 10, 1999 8:00PM (UTC)
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Dear Mr. Blue,

I can't get laid to save my life. I'm 30 and haven't had sex in
five years. It seems every woman under the age of 30 either has
a boyfriend already or doesn't want one right now; at least she
doesn't want me. I'm intelligent, successful, in good shape and
better than OK looking. I even smell good. For a year and a
half I avoided looking
for a girlfriend, testing the theory that "you'll find her when
you're not looking." No such luck. All I can figure is that
I'm too nice and too open. How do I learn to be the
kind of jerk that women will actually date?



Dear Blue,

You need to lift that age restriction and open up the
field to the Experienced Woman of 40. As you've found,
available 30-year-olds are in short supply, and the best ones
are tangled up in marriages or romances or are discouraged and
taking a vacation from men. Whereas in the 40ish category,
you'll find mature, experienced women who will charm the pants off
you, and you will wake up in the morning, exhausted and giddy,
your ringlets pasted to your forehead, and she will have left a
beautiful thank-you note on the pillow and then you will detect
the unmistakable aroma of fresh coffee and blueberry pancakes.
Yes! I swear, I am not making this up. Women change in that
decade. They learn to appreciate us. Broaden your horizons, Blue.


Dear Mr. Blue,

This summer my jobs entails that I travel each morning from the
suburbs to the big city to get to work and to make money for
school. Lately on the ride home there has been a girl, about my
age, whom I've become interested in. However, while normally I'm
outgoing and fun, I can't seem to think of anything to say to
this girl.

Besides "So, we take the same train, huh?" what else can I say to
start a conversation and see where it leads?


Train Rider

Dear Train Rider,

It's been so long since I sidled up to a
beautiful stranger on a train and said the magic words that made
her love me forever, I can't remember just how it goes. But if
you and this girl haven't spoken, what exactly is it about her
that interests you? Is it her pale angular waif-like fragility?
Then I guess you can ask her about that. Say, "Excuse me, but are
you getting enough for breakfast?" Or you could say, "Do you mind
if I talk to you for a few minutes? My brother died last night."
Or you could comment expertly on the weather. First, however,
you'll need to sit down next to her. You stand next to where
she's sitting (assuming the seat next to her is unoccupied) and
you lean forward at a 36-degree angle and you say,
"Quelle est la place la moins cher?" And then, quickly, you say,
"Oh, I'm sorry, I thought you were French." And then you say,
"May I sit here?" She ought to look up and flash a beautiful
smile and say, "Of course, sailor." If she hangs her head and
looks sullen and grumbles something unintelligible, then move on,
and try again next week. If there is a little old lady sitting
next to her, flash your ticket and tell her she's sitting in your
seat; say it as gently as possible. If there is a big beefy guy
with slicked-back hair in a blue suit and a black shirt and a
white tie, you'll have to tell him to move and there may be
fisticuffs. Love is never simple, even on a train.


Dear Mr. Blue,

I am about to enter my senior year of college and am very unsure
of what course
I want my life to take. I have been dating a woman, off and on,
for several
years, and she has just recently graduated. She seems to know
exactly what she
wants and insists that her plans involve me. I feel a strong
desire to lead a
life of adventure, but I also know that I love this woman deeply,
and as a
result I have a conflicting suspicion that I could fit into the
path she has designed for herself. I am sure that if I do not
follow her to
the city in which she is now living, it will end the
relationship. I don't
know how to choose between something that I know is substantially
and something which could be wonderful, but might be a disastrous

At the Crossroads


Dear At,

You don't seem ready to follow this lovely person to
that city and to that comfortable life she has in mind for the
two of you. She has a plan and it's not your plan. You have
misgivings, and you shouldn't stifle them so that you can follow
her script, even if you love her deeply. If you crave adventure,
then right now, exactly now, is the time to seek it, while you're
young and independent, so you don't wake up 10 years from now
wishing desperately that you had. It is not a disastrous mistake
to want adventure.

Dear Mr. Blue,


My parents have been married for 27 years and are just in their
mid- to late-40s. They have been great parents to me and I
love them
both very much. But lately I've noticed that they're very
distant with
one another, and short-tempered on the few occasions they do
talk. When
I last visited their home, my mother broke down and told me she
was very
unhappy, that she loved my father but didn't like him much
anymore. She
said that he was acting increasingly crude and disrespectful
around her,
using profanity and looking at pornography on the Internet. When
tried to talk to him, he said that if she didn't like the
situation, she
could leave. My mother told me she is seriously considering
She said that perhaps it's inevitable -- when people grow older,
grow apart. I love them both, and have noticed the changes
between them. But I want
them to stay together. I just don't know how to fix things
them. My father won't even admit there is a problem. Should I
trying to talk to him? Or should I just support my mother in
her way back to happiness, with or without my father?

Deeply Saddened

Dear Deeply,

A grievous problem and one you should stand clear of
unless there is need for intervention to protect them from each
other. You don't know how to fix things between them, and maybe
they don't even want you to; maybe it's an old argument that
they've polished to perfection, like a play, and they are looking
for a third character to give it a little more zip. Of course you
should talk to your father, but listen to him too, and don't try
to corner him. It sounds as if your mother has enlisted you on
her side of the conflict: Beware of that. But maybe you should
find ways to see her apart from your father, to give her some


Dear Mr. Blue,

I want to know if it's possible to fall in love with someone that
don't actually like. Or is what I feel simply lust? Is there a
gray area
between the two that I have somehow wandered into? I admit that I
this man extremely physically attractive, and that certainly
indicate lust. But on the other hand -- despite the fact I am in a
relationship -- I find myself fantasizing about marrying this guy
having his children. I'm pretty sure he'd be a terrible choice.
again, I haven't married the steady one, either.

Gray Skies in Vancouver

Dear Gray,


It's human nature to be fascinated by the
impermissible and has been since Eve munched the apple. And in
romance it seems to particularly excite people. So many wild
operatic love affairs between wildly inappropriate people. Men
going crazy over foreign women, educated women of exquisite taste
falling for hairy brutes, people looking longingly across a
crowded room at people with whom a romantic affair would be like
a car crash. You have an advantage: You get to enjoy the lure and
you know enough to avoid driving into the tree. So avoid it.

Dear Mr. Blue,

Could you give me an objective opinion? My boyfriend and I have
been close friends with a married couple for over a year and got
along great and then, one weekend, when my boyfriend was out of
town, there was a knock on the door. It was the husband, who
proceeded to sit down and tell me that he was "attracted" to me,
and I was a "stimulating" person. He said he had told his wife,
and she had encouraged him to come over and be "honest" about it.
I spoke to her on the phone after he left and she said, "We're all
adults," and was very nonchalant. I was very confused, especially
since I, in no
way, shape or form, had ever been remotely attracted to him. When
I told my boyfriend
he was very upset and said he felt betrayed. We haven't spoken to
of them since. What do you make of this situation, and should I

Startled in Idaho


Dear Startled,

Why call them? What more do you need to know?
What's the confusion? You encountered someone who is interested
in you sexually (you and 14 million other women) and who
doesn't interest you, and you sent him away. Apparently, he has
an interesting arrangement with his wife that covers this. Take
it as an experience and let the other folks be whoever they are.

Dear Mr. Blue,

I am an energetic 40-year-old woman living with a wonderful
man. We've been together about two years and he is as close to
perfect as
he can be and I love him tenderly. But I am his first serious
girlfriend and I hate to think he may eventually feel stuck with
me and be afraid to leave me. I love his company and have no
desire to end this relationship, but I can't help but worry,
especially when I see cute little 20-somethings, and think he'll
go have some youthful flings. Do I worry
too much?

Romping in the Cradle

Dear Romping,

After a certain point, age doesn't matter so much,
except when it comes to having children, and if you feel that the
two of you are on firm ground (and after two years you should
have a hunch about this), then you shouldn't try to orchestrate
his life for him.

Dear Mr. Blue,

I'm in my mid-20s and though I get dates with women, nothing
happens. No sparks fly up. My looks are passable, I have enough
charm to get along, I bathe regularly and don't punch out random
passersby. Am I doing some dumb thing wrong that I just can't
see? Why the cool reactions?


Dear Clueless,

I guess the problem is that you're not powerfully
attracted to any of these women. (If you are, you don't say so.)
A woman is unlikely to send off sparks if she doesn't see any
emanating from you. Concentrate on the conversational aspect and
be an amusing companion and let the fireworks come as they will.

Dear Mr. Blue,

I'm a young (not yet tenured) academic in the humanities, in an
utterly satisfying marriage of 17 years to a phenomenally
beautiful and loving woman, with three gorgeous, healthy children.
I have the world by the ass. But my wife and I are both miserable
living in this godforsaken outback where my profession has led
us; we both miss Boston, where we grew up, but I can't find
work in my field there. I love what I do, but I'm not sure how
long I should pursue my career here. How long is long enough? By
what criteria does one measure?

Moses (No)

Dear Moses (No),

If you've lived there for five years or more and
you're miserable, really miserable -- not just restless but really
unhappy -- and you've made reasonable attempts to acclimate and
they didn't work, then make plans to pull up stakes and move.
That's my advice, risky though it be. Set a date, and burn your
bridge, and then go where you want to go and look for a job.
Misery does you no good past a certain point. Of course you may
have to settle for a job as a shoe salesman, or a maitre d', or
the host of a radio show, but it's important for you and your
wife to live where you feel at home.

Dear Mr. Blue,

I'm 40, with two failed marriages behind me, with charming
dilettantes who couldn't hold a job and who left me wondering
where in the heck they were at 3 o'clock in the morning.
Interesting but useless gentlemen. So, for two years, I've been
seeing a fellow who doesn't have an artistic bone in his body.
He is practical, dependable and kind, a solid citizen, perfect
to start a family with, but alas, in the course of a conversation
I made a reference to King Lear and my sweetheart asked, "Who's
King Lear?"

This has drawn me up short. He is a good egg, but there will
never be a meeting of the minds on a higher plane. I feel he will
never fully understand me. How can I learn to appreciate his good
points and recognize a good thing when I see it.

Not Getting Any Younger

Dear Not Getting,

If William Shakespeare had been drawn toward a
lovely woman in London and romanced her and it turned out that
she had never heard of King Lear, he wouldn't have felt, as you
feel, that she could never understand him. To the contrary. He
would have cheerfully told her who King Lear was and would've
read her all his favorite passages. You're being awfully
snobbish. The world is full of lightweights who, recognizing Lear
as Shakespeare and knowing they should know the play, would
affect familiarity. A man honest enough to ask the question is
worth your while.

Dear Mr. Blue,

My boyfriend and I are planning to move in together. We are each
25 years old and
very much in love in a committed, fun and sweet relationship. We
to make the move, though, because our parents are Catholic and
opposed to living together before marriage. We plan on being
married in two years, but there are other agendas we
want to fulfill before walking down the aisle -- grad school for me,
off debts for him. We appreciate our parents' position and value
their wisdom,
but on this point we disagree with them. It is a moral issue for
them; it
is a practical issue for us. My parents love him, and I know his
love me, too. How do we make this move without
isolating them?

Catholicism Blues

Dear C.B.,

It's your life to live and your decision to make, but if you're
in love and committed to each other, maybe your parents can't see
why marriage isn't a logical step here. Marriage won't get in the
way of grad school or paying off debts: Is there some deeper
reason? Is your reluctance a sign that you perhaps are not
equally committed to each other and that one of you is entering
this closer relationship in an attempt to convince the other? If
your parents sense this, they may be worried about the harm that
this sort of off-balance commitment can cause when the reluctant
party pulls out. How can you go through with this without
isolating them? You can't, and they will be hurt, but surely
they'll forgive you.

Dear Mr. Blue,

Some of the questions in your column are so far-fetched that it
like they're made up. Are they?

Quest for Truth

Dear Quest,

I don't know. I don't think so. I do know that they weren't made
up by me.

Dear Mr. Blue,

Eight years ago I fell in love harder than ever before or since
and then suffered the greatest heartbreak when we returned to our
respective colleges and he got back together with his

Now, after eight years without contact, we've begun dating again.
He and his ex-girlfriend have agreed to discuss in nine months
whether to give their relationship another shot. To me, he
expresses deep ambivalence about committing to this woman. He
also tells me that our relationship affected him deeply. All the
qualities I fell for eight years ago -- his wit, charm,
intelligence and spontaneity -- are still there, and anyone else
pales by comparison. However, I am wary of opening myself to
another wrenching heartbreak. Should I continue to hold this man
at arm's length?

Wary but Compelled

Dear Wary,

Give the man some room. Now is the time for him to
summon up his mental powers and decide about the ex-girlfriend.
One thing at a time. When he's made up his mind, then you can
make up yours. Your companionship at this point can only confuse
the issue. If he is a man simply seeking the nearest port, you
don't want to be that port.

Dear Mr. Blue,

I am 25 and have been with my 19-year-old girlfriend for one year;
I love
her deeply and would like to marry her someday. The problem is
that I am in
love with another girl, 18, who I grew up with and have
known for 10
years. We finally admitted to each other that we want to be
together. I
don't know who I want; I mean, I'm not sure if I just want the
other girl
because it's new and fresh or if I really want to pick her over
my girlfriend.
Any thoughts?

Caught in the middle

Dear Caught,

Don't try to choose between the two. You will only hurt somebody.
You need a third girlfriend, to sort of balance things out. Two
will only be fiercely jealous and come to hate each other, but
with three, they will be able to form shifting alliances and
intrigues, angling for your attention, striving to please you,
and you will be the beneficiary. I know this will seem -- how
shall I say? -- odd, but you're young and in your prime: Do you
think you could manage four? With four, you're going to see the
real payoff of polygamy, which is domestic calm. The women
make up a sort of herd, and the social structure is tremendously
stable, and you sit at the apex, and life couldn't be more

Dear Mr. Blue,

We have it all: two cute boys, good jobs with more than enough
money (and more than enough hours too!), a beautiful house in a
nice town, good friends. But somehow I hate coming home. We've
lost interest in sex, don't talk, don't even argue unless it's
about me working late again. Basically, she's tired of housework
and working and wants
me to cut down at work to help at home. I have the perfect job
now. What
do I do -- leave her now, immerse myself in work, or gut it out
till the kids are
grown and then go? We were happier when we had no money, no
children and just our
dreams for the future we're living.

California Dreaming

Dear C.D.,

You don't have it all. Your life is out of whack.
Listen to your wife for a moment; she's your partner, she's on
the scene and if she says you're working too much and she's
tired of picking up the slack, give her the benefit of the doubt
and rearrange things. It's possible. With experience and
confidence and cunning, a person can figure out how to reduce
almost any job to a humane scale. It's a wicked circle: you
coming home exhausted, dreading the hostility, missing the good
feelings that ought to be there. Make a change. She's giving you
a fair warning. Pay attention to your family and do your homework
and stop being a hot dog.

Garrison Keillor

Garrison Keillor is the author of the Lake Wobegon novel "Liberty" (Viking) and the creator and host of the nationally syndicated radio show "A Prairie Home Companion," broadcast on more than 500 public radio stations nationwide. For more columns by Keillor, visit his column archive.

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