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Dating Advice #119 - Older and Wiser?

May 9, 2009 | by Rosie Einhorn, L.C.S.W. and Sherry Zimmerman, J.D., M.Sc.

He prefers dating women half his age. Is there any reason not to?

Dear Rosie & Sherry,

I'm a single man, age 52, and although that sounds old to many people, it doesn't feel old to me. In fact, I'm still attracted to the same type of woman who has always piqued my interest -- women in their late-20s or early-30s.

I have more offers than I can handle to date women who are closer to my own age, but I can't help the fact that I really want to date younger women. Everyone tells me that I'm unrealistic, but every once in a while I hear of a young woman who falls in love with and marries an older man. Am I wrong to hope this can happen to me?


Dear Jack,

By turning to us for advice, you are looking for an objective assessment of your situation. An outsider viewing your situation would say, "I can understand why you would want to date young, good-looking women. But what would a 28-year-old want in a man old enough to be her father?"

Few young women seek soul mates who are twice as old as they are. Most of us seek a spouse whose experiences, lifestyle and expectations are similar to and compatible with our own. Frankly, it's hard to find such a "match" when a dating partner comes from another generation (yes, you are from a different generation than the women who interest you), and that's why most adults limit the scope of their search to a partner who is close to their own age.

Most young women who are attracted to older men seek surrogate father figures, maturity to balance their own insecurity, or someone with the means and inclination to be a "sugar daddy." Many marriages between a younger woman and older man are loving and successful. However, couples with a 20- to 25-year age gap are a rarity; it is difficult to sustain a long-term relationship when each party's goals are very different. The younger woman may expect to complete her education, solidify her ambitions, build a career, and eventually raise a family. The older man is no longer interested in investing time and energy into building his life; he's already done so and now wants to reap what he has sown. And if he does want a family, he surely won't want to delay fatherhood.

Even if the couple is able to fashion a mutually agreeable lifestyle, they may face an additional challenge as the woman matures and gains self-confidence, because this might upset the balance between them as she becomes more assertive.

If a woman gravitates to a well-off, older man because of the material advantages he can provide, she may not form an emotionally intimate bond with her husband. This type of marriage is vulnerable to any number of stresses, and may dissolve after the novelty wears off.

You say that you have many opportunities to date women closer to your own age. This is the population from which you are more likely to find someone whose interests, goals and lifestyle are compatible with your own. Ask yourself why you have such a strong preference for the same type of woman who attracted you 25 years ago. Do you think that dating someone closer to your own age is an admission that you are no longer young? Are you concerned that a woman in her 40s or 50s cannot have the same youthful outlook that you possess? Do you want your peers to envy you? Is dating a younger woman a symbol of virility? Are you afraid that if you marry someone your own age, you will leave this world childless?

Now look at your answers. If you are overly concerned with your image, then you are dating for the wrong reasons. Unless you change your perspective, you will never be able to have a courtship that leads to marriage. Furthermore, as time goes on you will face an increasingly difficult time finding women willing to go out with you.

If you look at marriage as an opportunity to father and raise children, remember that there are no guarantees that a 25-year-old wife can bear children, and the medical profession is increasing the likelihood that more women in their 40s can enjoy motherhood.

If you worry that you cannot find a soul mate among your peers who has as youthful an outlook as your own, ask yourself if you have ever taken the opportunity to get to know any of the "older" women you've been set up with. Chances are you've been so disappointed by the age factor that you haven't made the effort to try to enjoy your date's company and gradually get to know her, a process which in itself can take several meetings.

We suggest that you change your priorities and focus on meeting someone whose interests and goals are compatible with your own, and that when the two of you are out together you concentrate on enjoying the evening and learning a little about her. Give yourself a few dates before you decide if you have enough in common to want to keep dating her. You might be pleasantly surprised.

Rosie & Sherry


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