How to Pick a Lover

Posts tagged ‘May-December relationships’

Picking a Lover: The Trouble with Younger Men

Youth is that period when a young boy knows everything except how to make a living.
—Carey Williams

The problem with the young lover, of course, is that he talks; and when he talks, the naiveté which produces enthusiasm is less appealing. He simply does not know as much of the world as he will later, and so his conversation is more limited. For many young men, their range of interest is not very broad. His world revolves around sex, sports of many kinds, probably fast cars or motorcycles, beer and booze, and many kinds of recreational drugs. His palate is not very developed; so he will, perhaps, be as happy with beer and a burger as with beef Wellington—not a very varied menu, but at least he’s easy to cook for. If you let him choose the wine, it will likely be sweeter than you prefer. Instead of having a more acquired taste for good cognac straight, he will prefer a cold beer. In many ways, young men are simply simpler. They are more direct, less devious, with less guile.

And then there is the issue of money. The young man is, in most instances, relatively poor. Certainly, he is poor in relation to what he will have later on in life. He is just getting started and so is restricted in what he can afford and how he can live. Given that women, in general, make less than do men, that may mean that you make about the same amount. However, many women are still used to men who make more and who pick up more than their share of the tabs. With a young lover, unless he has a very rich daddy, you must be prepared at the very least to pick up half the expenses. Often, like the older man with a young woman, you are implicitly expected to provide some subsidy. That is not just woman to man; that is also the expectation of youth to age.

In most cultures, women have not been taught to pay their own way, much less to pay for others. But if you have a younger lover, then you must not only pick up tabs but must do so unobtrusively, graciously, and without resentment. This is easier in the abstract than it is the first time you realize that what seem like ordinary sneakers are in fact special track shoes that cost $250 and are absolutely essential for jogging. The young lover, like the young girl, expects to receive gifts, to have loans cosigned, and to borrow your car. It is not a con job, nor is it exploitation. It is simply the sharing of resources, which is what couples do. Only for a change, you are likely to be the one with more resources.

There is an absolute rule here which is worth emphasizing. If you are not willing to pick up tabs, don’t pick up young men. It goes with the territory, and so it should.


Cougar (Photo credit: Gamma Man)

When you pick a lover, how long do you want to keep him? For weeks and months certainly, but how about for years? Young men are restless types as are young women and fickle as well. Not having yet developed definite tastes, they are eager to sample a range of new experiences, which will include quite likely other women as well as other terrains. They need to move. They graduate from college—finally. They develop an unquenchable passion to see Egypt by means of a camel caravan. They want to try to make records or movies or to surf in California.

You don’t try to tie down the young lover, and you don’t follow him in his wanderlust unless you just happen to be going to Egypt or Los Angeles anyway. And you don’t whine when you are left behind, pursuing your own life as you were before you met him. You say, “Godspeed and good luck. Send me a postcard.” And you drive him to the airport and lend him your carry-on bag and yet another fifty dollars.

Sometimes, he comes back; but usually, he does not, at least not as a lover. If it has been a good relationship between the two of you, he may well come back as a friend, as if you were an aunt, and proudly introduce you to his new girlfriend. She’ll probably be a pretty little thing, fluffy and very young. You give them tea and crumpets—or more likely beer and peanuts—and send them on their way. Eventually, you may have to spring for a wedding present as well.

The younger lover is likely to be a bird of passage, and such birds can be of considerable appeal. But do not confuse them with the lovebird who mates for life.

The Older Man as Lover: First Love, Last Love

Men always want to be a woman’s first love. Women have a more subtle instinct: What they like is to be a man’s last romance.
-Oscar Wilde

One advantage of being with an older man is that whatever proclivities he may have had in his youth for sowing wild oats, he is now likely to be past that stage. He may now have become more concerned with the quality of his erotic relationships than with the quantity. While there are no guarantees, he may be more content than a younger man to settle down with one woman and concentrate on one relationship at a time. He is also more likely than a younger man to have come to terms with his work and to be ready to devote more of his time to relationships and to the cultivation of an enjoyable personal life.

The younger man, especially the ambitious young man on the make, has a lot of energy; but he is often too busy trying to be successful to make time for a full private life as well. The older man may have less energy, but he is much more likely to devote his energy to you than to expend it on many other concerns. Young men are great for starting revolutions, given their considerable energy and unbridled ambition; but these traits do not necessarily make them good companions unless, of course, you want to start revolutions too.

An older man has the advantage of perspective. He has the ability, born of experience, to recognize that everything that seems to be important is not, in the long run, really that important. He has seen relationships come and go—perhaps even marriages come and go—and he knows that, in spite of it all, most people survive. A large part of the so-called mellowing process is simply a consequence of his lower energy level: he is too tired to be bothered getting all steamed up over every little thing.

If your older man is past middle age and is approaching what must be faced as old age, he will have a “September Song”; but he is, no doubt, thinking that he does not have time for the waiting game. That in itself can add a certain poignancy which can be romantic. Often, the older man is grateful for what he views as a second (or thirty-second?) chance at a love relationship, and that gratitude can be a welcome contrast from the taken-for-granted attitude often apparent among one’s age mates.

Cover of "The Lover"

Virtually, all May-December marriages, and quite a few May-December relationships, involve an unspoken element of exchange in that they just happen to involve a relatively rich older man and a relatively poor younger woman. A real advantage of the older man is that he is usually willing to play the role of sugar daddy to some degree. His accumulated resources, plus his chauvinistic attitudes, combine to make him quite willing to pick up more than his share of checks. As long as you are having a relationship with him for his own sake and not for whatever money he may spend on you, then that seems like a reasonable exchange. It is not so much a matter of men paying for women as older persons with more resources paying for younger persons with fewer resources.

Remember, however, that if you become involved with an older man for his money rather than for his beautiful gray hair, you are likely to discover what seemed to be a sugar daddy really turns out to be a saccharin patriarch. The older man is, by definition, a man with a past. Do not begrudge him his former lovers or his former wives. Decades ago, some nameless winsome girl began to teach him what he is now showing you. Other women, wiser women, maybe wounded women, have taught him how to love. Out of their experience, their pleasure, and their pain, he may have developed an ability to be tender and a confidence born of maturity.

If you think of the women from his past at all, it should be with gratitude. Peter Ustinov observed that “parents are the bones on which children sharpen their teeth.” The same might well be said of first wives. And of first husbands.

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