Dating an Older Woman

Let’s play a guessing game. You have this undeniable propensity for dating older women – we say undeniable because you’re doing it consistently and you have admitted not ever dating someone closer to your age.

Our guess is that:

You have a comfort level with older women that you never felt with women your age.
An older woman does not intimidate you as much as the spring chickens that you’ve seen on campus and in the office
An older woman’s retirement fund is more than sufficient compensation for her wrinkles and her sagging triceps
You’ve always had this secret admiration for your mother – the truth is you haven’t outgrown Freud’s Oedipus complex and you fantasize about those things that Freud became famous for
You savor the experience and wisdom of the older sex
You love her and her age has nothing to do with a character quirk, a disease or a need for financial security on your part. You love her. Period.

If any of the first four reasons apply to you – be truthful now – then we suggest you have a session with a behavioral therapist.

If you staunchly defend that it’s for reason # 5 above, then we’ll say, “carry on, ole boy!”

Dating an Older Woman – Certainly not a Social Crime

Dating an older woman neither merits a psychological evaluation nor a police clearance. The act itself is not wrong. It’s the reasons behind it, especially if it’s one of the first four above. If younger women who are dating and eventually marrying older men are more the norm than the exception, then there’s no reason why the opposite can’t happen – just as naturally and as easily. Men who like older women should not have to go through a subtle condemnation.

Alright, an older woman makes you really comfortable in her presence. Her age and experience are responsible for those sparkling conversations you have over candlelight dinners. You’re absolutely fascinated with what she knows, what she’s done in her life and where she’s traveled. She does not speak of inanities, does not do foolish things that make a man wince. She seems to be “with it”, totally in control of her gears and bearings, and much as it makes you blush, an older woman definitely has mastered the art of bedtime tricks that you’ve come to enjoy and luxuriate in.

And goodness, that retirement account sure is inspiring. She’s confided in you about her assets and liabilities (very little liabilities if we might add) that you think – and giggle – of your friends who are constantly complaining about how they are getting into debt because their girl their dates don’t like footing the bill. These young chicks need to save their allowance to buy life’s artificial support systems – make up, nose lifts, dermabrasion, leg waxing and overpowering scents that reek of acrylic paint. You’ve told your friends time and again that dating an older woman is different, but they’ve given you the “you nuts” look.

By comparison, your older woman friend stands out. She’s not only financially secure but sports a high emotional IQ. She does not bore you with questions like “am I too fat in this dress?” or “you think I should shave my legs now?” No, she’s past those questions. Even if you gave her an honest answer, she couldn’t care less. She’s probably even forgotten that she asked. Instead, she’ll smile and look at you with pity and say, “why don’t I pick up the tab this time? You’ve probably used up your weekly allowance. My son does it all the time.” She’s compared you to her son – ouch – that’s okay. She has qualities that thrill you no end.

Dating an older woman because you’re secretly in love with your mother means that the Oedipus complex still runs strong in your veins; that is, you haven’t done much growing up in the last few years. You need to play catch up. If you confess to your woman that you’re hung up on her because she reminds you of your mother she’ll find someone else who is really interested in older women. Much as they are emotionally mature, they don’t want to be looked upon as a mother figure – trust us on this one. They want to be thought of as desirable sex objects. Even in their late 40’s or early 50’s. No doubt many of them still hold that magic. Their magic stick is shinier and more efficient than those waved by young women.

It’s what one man said on cyberspace the other day: “Women love to feel appreciated, desired, alive, and when you’re an older single woman, there’s no one better to fill those needs than a man who is a few years younger.”

So…it must take two to tango.

The How-To of Dating an Older Woman

Younger men have been known to be genuinely in love with older women. And they’re well-adjusted too. They show no traces of the Freudian theory, nor are they interested in financial security. And they don’t care if the cellulite shows or the once jet-black hair has turned gray.

Younger men who are genuinely in love with older women are totally blind to their menopausal symptoms, their occasional unavailability (“I’d like to spend Saturday night in the cottage – alone.”) and their complete indifference to the flirting male. Would you believe NOT many of them throw jealous tantrums?

A few would even encourage you to play the field once in awhile.

If the laws of attraction dictate that older women are for you, it might be wise to pay attention to a few “niceties.”

Age is just a number. If her being older by 10-15-20 years bothers you one bit, then perhaps you’re better off with Tracy or Lisette or Jamie on campus. Stay away from Mrs. Robinson. There may be a generation gap, but this doesn’t hold much weight anymore these days. When you’re having conversations, pay attention to how you respond to her words. Older women have developed some sophistication and will immediately be bored if you can’t carry the conversation off
Older women appear to be self-confident and poised in thought and deed but a few of them do harbor insecurities because of the competition offered by younger, firmer and sexier women. They still appreciate it when you tell them how fantastic they look and how that dress so becomes them. Be generous with the compliments but make sure they are sincere
The first few dates may be difficult, only because there’s a need for both of you to adjust to each other. You need not feel you have to act more mature than you are; she may also try to act a little immature just to play the part. She is aware that there is an age gap but if that’s not a problem with her, it shouldn’t be your problem either. Enjoy her company but polish your conversational skills (we keep emphasizing this) as you don’t want her to start thinking that you’re socially backward. Don’t feel that your age and lack of experience are a handicap in your relationship.
Older women are the product of past dates and marriages. Don’t ask her for a history of her relationships if she’s not inclined to discuss them. Besides, you’d only be reminding her of her bitterness and disappointments. The reason she agreed to go out with you is she wants a break from the past and is ready for another romantic adventure which could very well lead to a mutually satisfying relationship.
Bear in mind that even if an older woman is not as demanding as a younger woman when it comes to chivalry and gentlemanly habits, cultivate the gentleman in you anyway. In fact, show her your British boarding school manners – a lot of women we know fall for that type of upbringing.

Dating an older woman, like we said, is not a social crime. You have as much right to date someone who attracts you and who fits the bill. You’ll probably have a lot of explaining to do to your family and peers, and maybe go through a little awkwardness in the first few months, but all these “teething problems” should be resolved in no time.

Sweet, young thing: that’s you, buddy!

Article first appeared at TSG VICE. Click here to go there!