What I’ve Learned About Dating in My Sixties

It’s not what you might expect, in some ways it’s worse than you expect, and in all ways it’s funnier than you might imagine

If the notion of dating past sixty brings up visuals of two doddering ancients waddling over to the shuffleboard courts, let me disabuse you.

While I’m sure that there may well be a certain percentage of that in some of the over-55 communities, and I can only speak for myself and those of my inner circle who fall into the same age bracket,

that ain’t happenin’, man.

One of my closest friends, who is gay, told me last year that we have the same desires in our sixties as we do much earlier in life.

Yes. Maybe. Kind of. Not always, at least for me. It depends.

Some things- depending on what is important- can and do change as we age. Physical needs? Many of them stay the same. What does change, what can change, is what you and I are willing to tolerate when we date later in life.

The kinds of trade-offs we might or might not be willing to make just to have company, a partner. I think that does change. In fact, based on what I see, it can change a great deal. While I would posit that generational differences come into play here, there are some hard truths about how the more things change, the more they stay the same.

About dating that is. And gender politics.

To set the stage, yesterday I read a piece on dating from Sean Kernan, who is in his mid-thirties. I really like his stuff, and often take advantage of his good nature to write funny comments in his thread. Sean wrote about dating in his age bracket, and the lessons he’s learned from dating women who were, for him, too young.

A good bit of what he had to say rang true for me, albeit in a very different direction. Once I turned the ripe old age of 31, I dated younger men. From six to 22 years younger. (All right all right, I waited til I was fifty for the 28-year old. That would definitely have given cradle-robbing a brand new name.) For many of the same reasons that Sean discussed, albeit from the older woman/younger man side of the ledger. Part of that is the increasingly distressing behavior of men close to my age, which if anything seems to be ramping up the older I get.

Lest any of my readers immediately leap to the sex part of it, just…PLEASE. I am whip-smart (for at least two minutes every day) highly accomplished (as long as you include professional mud-wrestling) and very athletic (as long you rate sprinting from the couch to the fridge for refills during binge- watching). Sex is in many ways the least of it, although there is this:

I am indeed an athlete. Even though I went through periods of obesity, I never, ever stopped exercising. If anything, I work out far more now than I ever did as a kid.

Most athletes I know, at any age, really enjoy sex. Yeah. We do. But, and here’s a caveat for ya: I enjoy sex with someone who knows what the hell he’s doing and has enough interest in his partner to give a damn that she’s enjoying herself.

Well. That took care of a rather large swath of the men I’ve met. And, in fact, for nearly my entire adult life.

Happy to be friends, and I have plenty. But if a guy genuinely does not care about himself enough to be responsible with his diet and exercise program, we are in no way a match. I prefer athletes, at least someone who has his own sports and love of life that are served by regular, energetic exercise.

It might be somewhat helpful if a bicep curl for the dude in question doesn’t mean at the corner bar with a pint.

Dating when you aren’t a drinker, you have a lifetime commitment to exercise, feel strongly about personal development (across all spheres) and have high integrity, well. Plan to spend a lot of time alone. To wit:

WOMEN WHO DON’T DRINK RECEIVE 24 PERCENT FEWER MESSAGES THAN WOMEN WHO DO.

Plenty Of Fish put together graphics describing the most “desirable singles of 2014,” based on what they observed heterosexual online daters liked in the opposite sex; the site claimed that women are more likely to get messages if they are Catholic, have a dog, earn more than $25,000, and don’t have a masters degree. Men get more messages if they are Christian, brunette, high-earners, and PhDs. (this quote is from the article below)

If you read this the way I do, especially because I don’t fit most of these categories, I’m not good dating material. Which is perhaps why, in my 67-year-long life, I have been given flowers twice. Men don’t bring me flowers. When I was in my twenties, they raped. As I’ve come into my own, more often they deliver insults rather than irises.

You can read whatever you like into that. My journey has entailed a long, difficult evolution from giving up very large chunks of who I am in order to secure occasional company, to someone who frankly doesn’t give much of a damn any more.

Dating per se isn’t of much interest. Good company is. That, of course, is defined individually by each of us and, boy, can that change over time. Boomers were perhaps the last generation of American women who started out, at least, still believing in the white picket fence, domestic bliss, and all the other happily-ever-after Disney promises that for so many were not, and still aren’t guaranteed.

For my part, I was never motivated to have kids and do the domestic thing. That alone, since my generation of men had very specific expectations for what women were “supposed to do,” marked me as undesirable as a partner for the distance. My choice to leave home at 16, be self- sufficient and join the Army virtually guaranteed that I would not be dating material. Instead, I’ve been much like the Lamborghini at the car dealership, the girl they drove around the block a few times to impress their friends. (Shannon Ashley wrote something very similar about this not long ago. ) Guys would drive the Lamborghini around the block, then return it to the dealership. Then….

They took home the wood-sided station wagon to produce progeny.

Said station wagon could well have been the class valedictorian or the homecoming queen. The point is she was willing to produce, and align most, if not all, of her immediate future with her man. Kindly, remember the times. This started for me in the late 60s. It’s not in any way a slam on women who marry, who have kids. I’m simply making a point about my relative undesirability as a partner.

In a nutshell, that’s been my dating life. If I’ve had company, I’ve had to tamp down, shut down, carve off and trade away large pieces of my person, my larger-than life personality. Over the decades I’ve done this less and less. Not only have I ceased trying to force myself into an acceptable skin suit for the sake of male company, I’ve gotten more outré and outspoken, and lived an even more extraordinary life. As a result, fewer and fewer men show the slightest interest. Often those who do show up bring weapons. To wit:

But to be fair, I’ve tried. I have given a good number of men a fighting chance. You’ve been single as long as I have, that’s a decent number.

I kept trying. Some of this turns out to be pretty good comedy fodder.

To wit:

Guy shows up at my fave local restaurant. He’s a little older. Profile photos were embarrassingly inaccurate. We order dinner. Over food, on a first date, guy proceeds to regale me with all the intimate details of his recent colonoscopy.

DUDE. Just. Fucking….DUDE.

You cannot make this shit up. You just can’t.

Not an isolated incident, either, especially as men reach their later decades and are ISO a caretaker. Dude. Hire a fucking wet nurse.

Fellow female online dating Medium buddies? Here’s what I get when I look at my inbox (and remember, ladies, I’m 67)

“Hi.”

““Hi Sexy.”

“I like anal sex.”

“Want to fuck?”

Straight downhill from there.

For a longer and funnier list, please see this:

I got every single one of them. Regularly. While this didn’t make the list, here’s my personal fave: I love to laugh. To quote one of my favorite Medium writers Kris Gage: OMFG.

Or, when some dumbass writes that “my friends would say that I am….”

Precisely how much did you have to pay them to compliment you, Skeezix?

Especially to lie for you.

Most of the time when I have that very rare date, someone walks up, is righteously shocked to find out that I do indeed look like my photos, that I am indeed everything I said. At my age. Watching them try to carry on a conversation after they lied on their profiles (81% of us- YES-about age, weight, salary, hair or lack thereof, physical prowess or lack there of, I could go on) is like watching someone pass a kidney stone.*

To wit:

I don’t lie on my profile. That’s completely, utterly and totally Out. Of. Integrity.

I love being kind. Generous. My love language is gifts. I’ve had my bank account wiped out several times by men who were VERY happy to take advantage of that largesse. I made those choices in part because I wanted company. Damned expensive choices in far more ways than just what might have now been a modest retirement fund.

Kindly, I would love to hang out with a guy who doesn’t think what I love to do - epic adventure travel - is unseemly. Or unladylike (REALLY?), or that my love of things wild and extraordinary threatens his sense of power. His agency over….(women).

And now: about those penis photos.

Too bad I didn’t save them all from 1998. I have been regaled with more penis pictures than the entire Kappa Sig Fraternity, all the years since 1929.

I should have created a penis museum. Honestly, and I can only speak for myself here, I am so tired of seeing unsolicited penises that if I am spared the sight of them for another five years I’d be quite happy for the goddamned change of scenery.

And frankly, guys, I massage Very Large Animals. When I work on a male creature- horse, tiger, elephant, whatever, they drop. They drop because they are immensely happy and relaxed. You want to see an impressive penis? Stand next to me next time I work on the stud for a local stable. That will definitely put you in your place.

The penis-as-calling-card outreach (or shall I call it out-retch) is universally shared, as is the completely unjustified love affair with the single least important part of a man. Unless of course you’re in porn.

And no. The older you get, in these regards, not a damned thing changes. If anything it gets more desperate in precisely the same way desperate women turn to Botox.

In the last few years, the penises started looking distinctly more like Mitch McConnell’s neck. Maybe they all did, but that’s the nature of the beast.

Uncircumcised men’s penises look like pigs in a blanket. Universally unimpressive. It continues to amaze me that men are so invested in such a ridiculous-looking appendage, when if they would bother to build their character, they might have a hell of a lot more to offer. Brains, emotional maturity, intellectual development, character and HUMOR are sexy as shit.

A combination of all that? Haven’t found it yet.

Is this all men? Of course not. However, my frustration is that the very best men I have had the pleasure to know are married, partnered, prefer other men or are my closest friends. Still, were it not for these Princes, and they really are just that, I’d have given up a long time ago.

Which to my mind, as I wend my way towards the big 7–0, reinforces the impression that when it comes to the opposite sex, the male intellectual capacity follows the blood flow, largely draining approximately 107 IQ points from whatever may or may not have been present initially. Age doesn’t improve anything, other than ensuring said recipient of blood flow often doesn’t respond as desired.

And then there’s this:

There seems to be this widespread and inane assumption that as women age past sixty, we somehow develop this rapacious need to see a penis.

Yeah. I see one — a really ugly one — every time I see Trump. Or it may just be he’s out sunbathing his asshole (yes that’s a thing, the entire Administration’s been doing it since Day One). Theirs are set squarely on their shoulders.

Why is it that when I think of politics, pricks come to mind? Oh, you mean because a few very high profile ones (including a Presidential candidate) were so determined to show me theirs?

As well as a few celebs. Will. You. Please, guys. Keep it zipped.

But wait, there’s more:

Guys my age, God bless partially-woke Boomers, apparently still see women as arm drapery. To that, I still get this:

Some folks think that people like me- at 67- should take this as a compliment. That at my advanced age, I should be so fucking grateful that ANYONE is paying attention to me, even if it’s condescending. My response is unprintable, even for me. Why someone who is grotesquely out of shape and even more grotesquely out of touch seems to think I would trade what I love to be locker-room fodder for a flaccid penis is beyond me.

Will. You. Please.

But then, they’re not thinking about what we as women want. I said earlier that our desires- as in, to feel desirable- don’t fade.

And for all of my younger women Medium buddies who fear (not without reason, but it’s all fake news) that somehow, the morning you wake up on your sixtieth birthday, your vagina, along with your clitoris, somehow quietly fall off your person and roll away under the dining room table never to seen again, kindly.

I might refer you to my sexy Medium buddy Vienna De Vega who, given the fact that she is (I think) still partnered, has a great deal to say about sex after sixty. And seventy. She’s a yogi. Athletics tend to keep you juicy.

We still enjoy sex. In fact, probably much more so later in life, because we know what we like and are far more likely to ask for it. But on our terms. And in all fairness, any more than a man particularly enjoys having sex with an unresponsive two-by-four plank, we women have gotten a hell of a lot more picky as we age.

I can tell within five seconds after someone starts kissing me if he’s going to be worthless in bed.

I can also tell within about five seconds after someone shows up at my local Starbucks just how much that person lied on his profile. At that point I’ve already scanned the place for an exit door (close to my chair) or a window I can shimmy out of in the women’s room. I’ve bloody well done it, too.

Because for my part, after a long and sordid history of men who rape, take, grope, and grab, I am done with being polite past a certain point.

Get a fucking plastic doll, gentlemen. Learn some manners.

Besides, after finding myself a buzzer that famously delivered more than sixty orgasms in one sitting (I needed oxygen), I hardly have the patience for a guy who can’t be bothered to learn how to help me achieve even ONE. And the penis doesn’t do it, gentlemen. Learn your goddamned female physiology.

To that:

A note to my female readers: kindly inform Mr. Wonderful of the above next time he blames YOU for not being able to have an orgasm just because of the Mighty Sword. And kindly inform Mr. Wonderful that if he really wants to be a halfway decent sexual partner the word FOREPLAY might need to get branded on his punkin forehead.

I get a lot of likes on this comment that I made when someone on Medium mentioned an “unselfish lover:”

It’s been so long since I had one of these I have decided to put this on the Endangered Species List.

And kindly inform Mr. Wonderful that if he is righteously offended by your “number” (please read: you’re not a goddamned virgin), said “number” allows you to -GASP- realize just how inept the man is in bed.

The good ones care. The good ones ask. The good ones invest time and compassion. I can count the good ones on the fingers of one hand. That is being generous because my “number,” given my age and my nearly life-long single status, is considerable. And BTW gents, the good ones wear condoms without being asked. Just saying.

I am no longer the slightest bit surprised that women end up preferring each other over men.

I no longer have the time or patience. Or the interest for that matter. I’d rather ride a half-wild horse, kayak another choppy ocean or massage another enormous animal that could kill me with one move. The thrill of skydiving, bungee jumping, summitting a huge mountain, and above all, riding a magnificent horse at full speed across dangerous territory and surrounded by all manner of incredible animals is one HELL of a lot more attractive to me at 67 than putting up with puerile backseat attempts at grabbing my tits or having an argument about safe sex.

Grow. The. Fuck. Up.

I have spiritual, emotional and intellectual work do to. Deep work. Hard slogging deep work. Men have always and forever gotten in the way of that deep work, for I have all too often found myself spending so much time shoring up their delicate egos that my own development has suffered. Yet, I miss occasional company. While that is true, the deep work is more important.

I like men. I really do. Even after multiple rapes, a lifetime of sexual assaults, brutish partners, and all the rest. I like men. These days, mostly, as friends, camping partners, guides, fellow riders and kayakers and all the other things I love to do. My most precious male friends are everything I’d ever want in a partner. And we’re too close as friends to test that boundary.

What I do want is a man who is courageous enough to develop all his available parts: his emotional being, his intellectual being, his physical being, his spiritual being- and not trade every goddamned one of them off because he worships his almighty penis above all other things in life.

With the exception of a rather badly behaved, mostly absent BF that I hung onto for reasons I have yet to truly fathom for ten years, dating in my sixties has largely pretty much precisely the same as it was in my thirties, forties and fifties. Before online dating. I spend a great deal of time alone, which I prefer more as I get older.

Because this is the deep work I am doing. The hard physical labor I do is just a small part of the work on all the human spheres. I mean to be a woman in full, which in my vernacular, means to be a human in full.

To that I wrote this:

I’m not Wonder Woman and I don’t need to date Bear Grylls. However, halfway through to my sixty-eighth year, I am done with baby men. There are very few, if any, men who want to play high, play hard, and play deep.

If there is indeed someone out there who does, and I happen to meet said gentlemen before I am shuffled off this mortal coil,** so be it.

*While I would love to take credit for this superb line, in the interest of honesty, I stole it from the Netflix show Longmire. After I got back onto the couch, having fallen off laughing. Longmire was trying to ask a woman out an on a date, and this was her response. Too good not to steal, but I give credit where it’s due.

**Shakespeare, Hamlet