Olympia's Thoughts on Dating Older Men

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Olympia, a professional consort, discusses power equity in relationships, & the grace required to deal with them.

When I was sixteen, I took a course at NYU in the evenings. A teacher at school had recommended the class to me because of the subject matter and also because she was friends with the professor who taught the evening sessions. Every Tuesday for a semester I sat among college students, elderly auditors, and the occasional continuing education adult for discussions on modern literature in America. I remember some interesting discussions, some even more interesting bibliographies, and a general feeling of interest. But what I remember most was the man who sat diagonally from me who introduced himself after class one evening, about three weeks into the semester.

There is nothing unique about a man inquiring after a woman, and I would never hold this anecdote up as such, but what was memorable about it for me was that I was sixteen, and the man who asked if he could walk with me to the subway was 34.

His name was Ron and he was a producer at a network news show. He worked the early morning shift and had never taken an evening continuing ed course before, but he was interested in Don DeLillo and thought this class might be right up his alley. That first evening we talked about the class and the book we were in the middle of reading Ė if memory serves me correctly it was Norman Mailerís An American Dream Ė and how we found the other students. In other words, our conversation was an exact duplicate of countless others being engaged in at that very moment as classes let out.

I didnít think much of the walk until the following week when Ron walked me to the subway again. After all, I assumed he knew I was a high school kid and just didnít want to walk to the subway alone when he could walk with someone he sort of knew.

On the third week I learned that Ron didnít take a subway that originated from the stop he walked me to and, in fact, lived in the entirely opposite direction. I learned this in a coffee shop that we stopped at on our respective ways home. We spoke more familiarly about movies and music, pop culture and news Ė nothing personal.

On the fourth week it dawned on me that Ron had not taken me for a high school student but had assumed, and not without merit, that I was another college student taking the course per a requirement. And I didnít know what to say. I knew it would be bad either way. I shouldnít lie and pretend I was a sophomore majoring in Philosophy or a senior majoring in Physics and taking the literature course to fulfill a core requirement; but I also knew that admitting I was sixteen, lived with my parents, and actively debating what to wear to prom would embarrass him terribly.

I knew this because I knew Ron liked me. I started noticing him looking at me, appraising me, listening closely to what I said and leaning in to hear better Ė or just to lean in. I knew that even though it was merely a flirtation, it would be embarrassing for him to discover he had been flirting with a legitimate teenager. And then I would be embarrassed.

I never told Ron and I never saw him again after the class. We never exchanged telephone numbers, and this was in the days before email addresses were the modus communicatus, and never saw each other outside of class and the walk to the subway, punctuated by another coffee or two. He inquired after my schedule a couple of times and I made up excuses, and then he stopped asking. Looking back Iím pleased with my handling of the situation and think he got the message that I wasnít interested, regardless of the reason.

It only gets tricky when the older man knows your age and is interested in you because of it.

Having discovered that I was not only interesting to high school boys opened up a wide sphere of fantasy. I started looking at men in the street, on the subway, in restaurants in a new way and wondered what ways they were looking at me. This led to some understandable experimentation: the college guy, the bartender, the man who picked me up in a bar I was too young to drink in. By the time I got to college I thought I had the whole inter-generational relationship thing well figured out.

Of course entering into a torrid and long-term affair with a married professor 50 years your senior can cloud the issues somewhat.

Because the biggest issue when involving yourself with an older man is the inevitable power dynamic. Whether consciously or otherwise, a young girl becomes infatuated with an older man because he has more. More power, more money, more experiences, simply more. I wanted a piece of that more and thought I could get it through a relationship without considering the reality that in a situation where there is more on one side, there is necessarily less on the other.

While none of us likes to think about it, all relationships deal in power. Successful ones find a way to share the power to the point where the individual struggles look like so much petty squabbling. But when you enter into a relationship where the power shift is so dramatically skewed from the outset, your must either change your expectations or change your comportment.

If youíre the kind of woman who doesnít mind deferring to a man in many matters, you can probably disregard everything I say here. If, on the other hand, you desire parity in your relationships and youíd like to enter into one with an older man, youíre going to, as terribly unromantic as this sounds, shift the power dynamic in your favor.

And if this sounds like a daunting task itís not. We, as human beings, are irretrievably vain. If I am attracted to a man because of his vast body of work or knowledge or social position, there is vanity in that. There is clout in that. Why, then, must I wonder, does this man who has so much Ďxí want with me? The unfortunate answer is that he wants my youth, my energy, my body untrammeled by years and wrinkles, and the satisfaction of knowing he still has the virility and prowess to attract a woman in the throes of youth. Herein lies the womanís chip.

Please understand, Iím not advocating detente, where both parties engage in a relationship of stalemates, nor am I suggesting that this power shift occurs in the open, rather I am maintaining that for a woman to feel good about herself while having a relationship with a man who assumes his position to be superior to hers, she must bear in mind that she too has something the other wants, and that the other will acquiesce to maintain.

What I am talking about is less an active display within a relationship, but rather a valuation of the self that will enable you, the woman, to avoid compromising yourself because of your awe, or fear, of the man you are with. Itís advice I wish I had been given prior to having my first serious romantic entanglement with an older man, and advice I have followed ever since.

Whatever your initial insecurity: Iím not smart enough, cultured enough, interesting enough, etc. to satisfy this man. I am lucky to have him and shouldnít rock the boat for fear that he will realize the above. Now turn it around and have him say his version: Iím not handsome enough, young enough, active enough, playful enough, in touch enough, etc. to satisfy this man. If you donít believe heís thinking those things, youíve already lost.

When I, as a 16 year old, realized a man in his thirties might have an interest in me, I ran through a litany of reasons why that was crazy, before realizing that whatever it was he saw in me, he saw something in me and desired me because of it. It was a hard idea to swallow, and I made innumerable mistakes over the next several years before realizing that I neednít denigrate myself in order to understand a manís interest in me.

This isnít a lesson that only applies to our relationships with older men, but it is highlighted within them. As a woman who, by trade, spends most of her time socializing with older men, and occasionally discussing these selfsame issues, please take it from me: their insecurities are just as great as ours, and it is only through having lived them more times than we that they surmount them enough to make us consider our own more strongly. It is not cruel to assert that we too are worth their affections, it is necessary to ensure that we get as much as we give out of these relationships.

I think, when I was asked to pen this article, the assumption was that I would discuss the benefits in dating an older man Ė there are manifold benefits indeed, but we wonít appreciate any of them if we donít first enter into the relationship secure in ourselves. If you think a man is more sexually experienced and that you wonít be able to measure up, without realizing it may have been thirty years since he had the pleasure of a naked woman your age, you are setting yourself up for a grueling inequity that will haunt you long after the relationship has run its course.

© Olympia Manet

Olympia is an exclusive consort in her late 20s, living and working in Manhattan. She writes a daily journal at Postmodern Courtesan ~ Note, this is not some average blog. Her website is filled with wonderful writings, detailing her work & life.


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