Last night a good friend called to tell me the following story:

“I was out at this bar the last night when I started talking to this extravagantly hot, 27 year-old. She asked me what I did for a living and, of course, I told her that I was a Fireman. The second she heard this, she screamed… ‘Oh my God, What Station? You have to introduce me to some of those hot, young firemen!’ It was at this point that my dick drew back into my stomach like a startled sea snail…”

To most people, this story may not come across as particularly interesting or unusual, but for a single guy in his forties, the demons’ in the message. See, he thought she was interested in HIM. And the jarring realization that his age had rendered him invisible to her as a viable dating prospect was coronary material.

Every day we live with ourselves. We look in the mirror, brush our teeth, run a comb through our hair and walk out the door: Day after day, year after year, decade after decade. And because this activity is a ritualized part of our daily lives, we don’t see the changes. But the changes are there. And no matter what products we use to delay the process, the reality that we are no longer 25 isn’t lost on those around us; including ‘extravagantly hot, 27 year-old women in bars.’

So the question is how do we appear to people who are, in some cases, half our age?

Like people twice their age?

Or like older guys with more expensive watches?

To us, nothing’s really changed. We feel young, and many of us look - and in some cases, act - years younger than we actually are.

But not young enough…and herein lies the rub.

Anyone whose reached middle-age has to face the fact that - no matter how we look or feel - we can’t outright cheat the clock. Let a few more years pass and we start to wonder whether or not it’s even appropriate to approach younger women. By ‘appropriate’ I’m thinking along the lines of …will she look at me like I’m out of my fucking mind for assuming she would consider me as a dating candidate? And the problem is exacerbated as we begin to lose touch with how old people actually are.

Is she 35?

28?

42?

22?

17?

We could be so off that she calls the police.

To remedy this problem, we have to let them come to us. There is no other way. And this includes the initiation of sex. It’s her call, period. 

This is what’s referred to as a conundrum, because while men are generally expected to initiate everything, we can no longer do so if our self-esteem means anything to us.

I’m excluding you sociopaths.
 
When I was 25 I could simply choose to date a particular woman and be reasonably sure she would accept my offer. But that was because I was a very good looking 25 year-old single guy, with all of the other requisite qualities that young, beautiful women look for; including education, background…and, yes, age relevance.

But when you double that age, things change, and you have to get a handle on the realities that come along with it, no matter what you were capable of nailing 25 years earlier. And believe me when I tell you I hear your pain if you happened to be blessed with all of the aforementioned qualities, but now find yourselves faced with the occasional rejection.

Many young women simply don’t give a damn how many bootcamps you put yourself through every week. Or how interesting you think you are. Or how talented you are. Or how successful you have been. By this time, life was supposed to have yanked you out of the game and onto your Lazyboy, somewhere suburbia, with a family, and an addiction to network television…which you have memorized down to a science.

But that didn’t exactly happen, and here you are. And with lots of company, by the way. 
 
The truth is, an ever-growing number of young women are actively dating older men; particularly in big cities, because these women tend to be more sophisticated than their fly-over sisters, and don’t appreciate being treated like objects by young men who expect feminism’s pay-off to include free sex. These young, professional urbanites routinely take them for granted, and have little to add to a given conversation other than a series of insistent nudges signalling that its now time to get naked.   

This notwithstanding, you still have to accept the fact that there are a corresponding number of women who can’t fathom dating older guys. They want Cinderella. They want Snow White. And they intend to ignore the odds against realizing these fantasies in a world where ”age-appropriate” relationships are harder and harder to find.   

This issue is becoming a major topic of late night conversation, as the population in the United States approaches 40, and the divorce rate goes through the roof. Eighty million of us - men and women alike - have to face the fact that while we have acquired things we didn’t have when we were younger, we still don’t get a pass to ignore the reality that attrition divies things up in equal measure. 
 
In the end though, I guess you could look at it as a toss-up. You can never have it all at any age, and anyone who’s been around a while can attest to this. But the message is always a little bittersweet.

…or you could just be filthy-rich and ridiculously famous…and forget about your age altogether.