Sleeping around: a beginner's guide to promiscuity

Herewith a chapter from my as-yet-untitled advice/memoir about death, life, love, and online dating.

“Eenie Meenie Minie Mo,” Charles Dana Gibson, 1926 (Library of Congress)

In 2020, I learned how to have casual sex. I slept with three men, twice each, within nine months.

I confess to a degree of clickbait in that headline, since I’m the beginner here. I never got beyond neophyte status—these recreational episodes were serial, not interspersed, and six is my lifetime tally.

That’s neophyte compared to serious players. Yet the best teacher may be the non-expert who recalls her step-by-step struggle with the skill, rather than the proficient who can do it in her sleep, so to speak.

Behind the Curve

Ordinarily, bedding acquaintances is the sort of thing you do in your 20s, not your 60s. I missed out on the first time around because by age 19 I was glued to the man I later married. Only as a widow did I have the opportunity and the appetite to play around.

As for most people at any age, promiscuity was a learning experience, not a destination. My dissatisfaction with each outcome reminded me that I am indeed the marrying kind.

Yet let me make one thing perfectly clear: nobody made me do this; all six events were eagerly undertaken by both parties. Moreover, I had a royally good time each time.

No. 1: Friendship Benefit

Rob had been my primary relationship a couple years earlier, then breakup, makeup, breakup, makeup, breakup, give up. Eventually I found out he was not only juggling me with a couple of women who thought they were his fiancée, we all were mistresses alongside his actual wife, alcohol.

But because Rob was a known Don Juan, I knew he’d be available when I needed him. And I did, after a heartrending breakup with a presumed Mr. Right, followed by a year-long drought of candidates who met my expectations for physical, mental, and financial allure.

Rob and I maintained a friendship of sorts as he broke up/made up with women who were more willing than I to be sidebars to his marriage. The temperature of our relationship rose in autumn 2019, and in January 2020 I flew to Florida with him on a house-hunting expedition. Indeed, I thought that house in Sarasota might be one I’d be visiting regularly.

Our sojourn involved transactional expectations of the sort proffered on sugar-daddy websites. He purchased flights, hotels, meals, and Viagra. I supplied amusing conversation and amorous avidity, along with Zillow research.

He bought the house; our revived romantic relationship bought the farm.

Outcome: Exasperation, then a shrug.

Once we were lovers again, we were no longer friends. Rob reverted to his boyfriend habits: sporadic text responses, random late-night drunk-calls, travel notions with no follow-through, no-shows for ticketed events. I went to a black tie ball as my own date, in tuxedo pants and velvet smoking jacket, and revived my online profiles. None of which were on sugardaddy.com.

No. 2: Singles Match

Jay and I had weeks of phone conversations before meeting. I preferred cutting to the chase for coffee or lunch with anyone interesting, but COVID had struck and these were perilous times for close encounters.

Jay didn’t meet much of my checklist, but he was charming on lengthy calls and quite a looker in photos. As was his lovely country home on a northern lake.

When he came to my city on business and met me for a walk in the park, he struck me as a kid playing an elder in the high school play, wearing a white wig and fake beard stuck onto a ripped teen body.

COVID logistics factored into my overnight visit the next weekend to Jay’s distant home instead of the usual dinner series. His reputation preceded him, thanks to a well-informed reporter: himself.

He mentioned, unapologetically, that he was currently seeing six women and had slept with two of them. As for history, he’d been married long enough to produce two kids, now adults, but not much longer. In recent years he’d had a horse farm and more with a female scion of Asian wealth, but he finally got tired of her periodic nastiness. So he’d taken up with a teacher, though rendezvousing with the equestrian continued for a while. The teacher was now history because she spent too much time doing grandchild daycare. Along the way, Jay had also slept with several other women in his tennis league, which is where he was meeting much of his bedtime talent.

OK, another Don Juan. But he declared he was seriously considering monogamy, he just needed to find the woman who’d convert him. And I love a challenge.

I made one thing perfectly clear on our first evening together. We were having sex only if and when we had an exclusive relationship. He kindly offered his own bedroom, sans himself, and slept in his cramped guest room.

Then, when I visited again, the sauna happened. And the hot tub. And the bedroom next door seemed like the natural place for two naked people to go next. On the third visit, all this was on purpose.

Then scheduling my next trip to the lovely country home suddenly got difficult. Jay and I still talked on and on nearly every night, but the next visiting opportunity kept getting postponed.

Finally, on a call, he launched into a metaphor-laden vision of my future reaching for the stars and ascending to my creative destiny. Back on earth, he admitted that he’d taken up with the teacher again.

She wasn’t as good a rider or runner as I, but she was experienced at tennis (he’d been trying to teach me), she lived nearby, and after a night together he could have coffee with her and send her on her way instead of having to spend the whole weekend entertaining her.

Still, I was an extraordinary person, he got a lot out of our conversations, and he really, really wanted to maintain our friendship.

Outcome: Fury, then a shrug.

“I don’t need another fucking friend! I have lots of friends! What I need is a lover, dammit!” I shouted into the phone.

Jay offered to remain a lover, if he decided he couldn’t do monogamy with the teacher. That pissed me off even further. “I TOLD you I needed exclusivity. If for no other reason, it’s a public health issue, especially these days!”

Anyway, as my best friend put it, Jay was two hours away in the wrong direction. Surely there were suitable men closer to my geographic center of gravity.

I apologized by email for yelling at someone who’d been a generous host, reminded him that my requirements had been clear from the get-go, and went back to dating site perusal.

No. 3: Too Much Too Soon

Will came the closest in this trio to possible partner. He ticked all the boxes: smart, educated, funny, slim, and apparently well-funded, since his lovely country home was mini-manse atop a dozen hilly acres. We shared a passion for golf, a box-tick tricky to find in smart, educated, funny, slim women.

Our first encounter, playing nine holes, ended with him declaring that I was exactly what my online profile indicated. While hardly romantic, this was high praise from a scientist. Also, I knew, not necessarily the common dating site experience.

Quite a find for both of us, but I was in no hurry to get physical. Until a few weeks later, after he made me dinner, when making out on the the sofa led to bed.

I started giving him the girlfriend treatment, taking care of his anxieties and baking needs during weekend visits. In turn, he started giving me the boyfriend treatment, à la Rob, not returning emails, texts and calls, and canceling plans at the last minute.

The girlfriending was too much too soon. Then Will decided the sex had been too much too soon, too—not because he had misled me, but because the expectations it opened up made him feel stressed.

For once, the competition wasn’t other women. Will’s plate was already loaded with an all-in job, OCD/ADHD-limited executive function, and pandemic-stranded adult children and dogs. To this, as 2020 progressed, he added unhealthy helpings of prostate misbehavior, back trouble, tick-borne illness, and storm damage at the lovely country home he’d decided to put on the market because it was too big for one person. Which should have been a big clue to the antidote to emptiness, the potential second person there.

Outcome: Ending with a whimper, not a bang (pun intended.)

Will declared he wasn’t ready for a relationship. I reverted to occasional golf and concert partner. He assured me that if he ever was ready for a girlfriend, I was a strong candidate. But he’d understand if I looked elsewhere, and I did.

Practical Matters

You may have wondered how a woman my age dealt with unexpected intercourse. First, I confess, no condoms. I trusted my partners, perhaps foolishly, particularly in Jay’s case.

Would I advise other post-menopausal promiscuity pursuers to do likewise? No. I’m a responsible journalist. But as a human I understand why you might echo my behavior, and I certainly understand why you don’t keep a pack of Trojans in your purse.

Second, what about the other thing you might not keep in your purse, lubricant? This is the more practical issue, in my view. Intercourse won’t happen without it if you’re a dame d’un certain age, There are plenty of other pleasurable things that can happen, but a lot of those are also enhanced by slipperiness.

The solution: Olive oil. It need not be extra-virgin (yeah, right!), and canola, corn or avocado may work too, but EVOO is what the men had on hand in the two unplanned cases. No. 1 was expected and hotel-based, so no kitchen supplies were available or needed.

Psychological Matters

While this sort of erotic recreation didn’t become a longstanding part of my lifestyle, I did enough of it to get an idea of what goes into a good time. The key factors seem to be equality of enthusiasm and parity of noncommitment.

“Permission” is not enough—it’s one-sided. When one party asks another for a go-ahead, there’s an inference of likely reluctance. Granted, somebody should probably ask something like “Shall we go upstairs?” when the going gets hot, but the agreement should be swift and sure. Ideally, everybody’s swept away with desire.

Neither of my encounters with Don Juans involved one-way seduction; both were back-and-forth. Moreover, while DJ-ism deserves its own chapter, I can testify here to the benefits of a lot of practice.

Equal absence of commitment can be more elusive, because what people say about it isn’t necessarily what they mean, if it’s discussed at all. But the worse the misalignment, the more you’re cruising for an emotional bruising.

Sex emerging from friendship may provide the most accurate understanding of where your partner stands. Long ago in college, my sister reports, she slept with half a dozen classmates in her senior year (very post-Pill, pre-AIDS). Was anyone disappointed afterwards, I asked, because one of them wanted the relationship to evolve? Nope, she says, we all stayed friends.

In my case, casual sex with Rob came closest to this standard. He wanted a legal threesome with his booze, and my refusal was already on record. The only future I envisioned with him was occasionally beneficial friendship, so the news of his marriage to a human merely bemused me.

The Will situation was almost opposite—he was boyfriend material. Our bedtime fun didn’t count as promiscuity so much as audition sex, which we both passed. Then he decided he didn’t want a girlfriend, at least not now.

Jay, on the other hand, was definitely in the market for a girlfriend; he just didn’t know how many. Both men were out of synch with me on the commitment meter, but for entirely different reasons.

I yearned after Will into 2021, even after I returned to online dating sites, because a better man was hard to find. Then I met one who was smart, educated, funny, slim, and apparently well-funded, since his lovely country home was on a dozen acres along the Hudson River.

He was both monogamous and genuinely seeking a girlfriend. And eventually, it turned out, a wife. Who turned out to be me.