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How to Lose Your Post-Divorce Virginity

She spent 23 years having sex with one man. Then a year after divorce, Nicolette Stein figured out how to climb back in the saddle. Here, her playbook.

When I lost my actual virginity at age 20, there was, of course, no Internet, no cell phones, no texting. I slunk away from the apartment of the man I’d chosen to relieve me of this burden, feeling nervous, elated, and a little slutty. I didn’t celebrate, or call any friends. I had enough shame over the sex-before-marriage thing (even though this was the 80s) that I kept it on the down low. But because I wanted a keepsake of the momentous event, for years I held onto the white Izod shirt I took from the guy–until it turned yellow and dingy, not unlike my once-pristine virtue.

The next morning, I called friends, opening up the conversation by singing, “I’m back in the saddle again!”

Contrast this with how I lost my second virginity—the virginity following my divorce after 21 years of marriage. Within seconds of returning to my hotel room after a late-night tryst, I texted this message to three of my best friends: “My post-divorce virginity is over. Call me if you’re still up.” My phone rang almost immediately. It was my night owl friend. I was barely able to talk I was so giggly and dopey in my lust fog. With the sheets over my head and talking in a whisper (my new guy was just on the other side of the wall), I recounted the whole story—I’d say I gave her the blow-by-blow but that sounds gratuitous in this context. I’m surprised the guy didn’t hear her screeching over the phone.

The next morning, I talked to the other two besties, opening up the conversation by singing, “I’m back in the saddle again!” Because I was working, I didn’t have time to call all the friends who needed to know, friends who had been through my divorce with me and wanted me to be happy again.

To keep all the important people in the loop, I sent out texts that gave the headline news—Woman Discovers She Still Has a Working Vagina—with a promise to fill in the story later. One friend, who is considering a divorce herself, texted back: “When you’re ready, I want ALL the details—especially how it happened! Like, did he hit on you, did you hit on him…etc.”

The short answer is I hit on him, but there’s more to the story. I decided to tell all here partly so I could send a link to all my cheerleading friends instead of repeating the details over and over. And partly because identifying what you want and acting on it require a certain level of courage that is difficult to muster after being with one penis for so long (23 years total in my case). I had to dust off my flirting skills and pull up my big girl pants (before pulling them down). Maybe my little escapade could inspire others…or at least give them something of a playbook.

Read More: Suddenly Single… Now What? Tales and Advice From the Online Dating Trenches

You Never Know When the Right Guy Will Appear

I was at a four-day workshop in Chicago before Thanksgiving; we were being trained on new Human Resources software, which let me tell you is total dullsville. The only bright spot is that one of the leaders was a tall guy from Denver, with a rugged face that looked as if it had seen many summers of high-altitude sun and lots of winters of stinging winds. How did such a guy, who looks made for the outdoors, end up in a dimly lit conference room in a Marriott? That was the question that first intrigued me.

Has there ever been a more incongruous idea than feeling hot for someone doing a Power Point?

The more I listened to him, the more I appreciated his easy affability, the way he told a joke, his patience with the pokey learners in the room (me being one of them). At drinks on the first night, I noticed that he was a good story teller. I learned he was a software developer Monday through Friday, but a dedicated mountain bike rider and snowboarder, depending on the season, on the weekends. I liked his politics, his self-deprecating humor, and was impressed by the books he mentioned.

We spent a lot of time talking over our drinks–Merlot for me, vodka martini for him—and I noticed that he was touching my arm a lot. Was he sending me a message, testing me out? Was this just his nature? If so, I was an arm toucher myself, and I felt muy simpático.

The next day, as I watched him go through a Power Point, it suddenly struck me that I had a crush on him. (Has there ever been a more incongruous idea than feeling hot for someone doing a Power Point?)

The Importance of a Wing Man…or Rather Wing Woman

On that second day, I asked my very married co-worker friends to sniff around to find out if he was single. I didn’t see a ring, but I’ve been told by those who’ve been through the post-divorce dating jungle that this doesn’t mean anything. Many married men don’t wear one, or possibly take them off when out of town. My friend was eager to help. “He’s absolutely adorable!” she said.

I was aware that at my age, almost 55, I didn’t have time to dilly dally.

At lunch, my friend and I sat at his table, and she steered the conversation around to his personal life. Any kids? No. Are you married? No. Are you seeing anyone? I guess you could say I’m between relationships.

I was almost breathless with excitement. He was handsome, interesting, just a bit younger, and friggin’ single. Now, how to telegraph my interest in him? I thought about it all through that afternoon’s class. Would I just throw myself at him? How embarrassing if he wanted nothing to do with me. I fantasized about kissing him. I couldn’t get any farther than that before my heart started racing dangerously. I considered calling a divorced friend for coaching, but decided I’d just have to play it by ear. Still, I was determined to act. I realized there were only two nights left of the workshop, and I was aware that at my age, almost 55, I didn’t have time to dilly dally.

Late that afternoon, before our scheduled group dinner, I decided to be pro-active and shave my legs. Better safe than sorry, right? But this being late fall and me living so long in the sex desert, I realized I had forgotten to bring a razor. I ran down to the little bodega near the hotel and as I was walking back through the lobby, I saw my guy sitting with his laptop. Having no bag for the razors (good environmental girl that I am), I tried to hide the package, afraid it might tip him off to what I was up to.

With the package behind my back, I asked, “Are you going to be here awhile?”

“Yes, what’s up?”

“Oh, I thought I might come join you.”

“Sure,” he said smiling.

I ran upstairs for my lap top and came back to sit beside him while we both checked e-mail. So romantic, huh? But in fact, after the deed was done, he would tell me that this was when he knew I liked him in that way.

When You See a Chance, Take It

After our email date, I went to my room to shave my legs and change. At dinner, I sat down before he did and there were only two seats left when he came to the table. “If he takes the one next to me, he likes me,” I said to myself, sounding a bit like the 13-year-old me who plucked daisy petals. He hesitated, but my brain waves were so strong that he finally lowered his very nice butt just where I wanted it. I smiled to myself. If I had a mustache, and thank God I’d checked for that before dinner, I would have twirled the ends and said to myself with a chuckle, “I’ve got you now.”

I laughed at his feigned formality, but didn’t waste a second.

Dinner was lovely. We talked about…oh, hell I don’t even remember what we talked about. I was drinking so much wine to calm my nerves. After dinner, I suggested the two of us go to the bar, and happily no one else from the workshop was there. Later, when we got off the elevator, he extended his elbow for me to take. I laughed at his feigned formality, but didn’t waste a second; I slipped my hand right through the crook and squeezed his forearm.

As we approached our rooms—so conveniently situated next to each other—I checked the hall to make sure it was empty. Then I summoned enough moxie to stop and turn toward him, still with my hand touching his arm. “I’m not letting go of you,” I said. We looked at each other for a long second and then before I knew it we were kissing. Oh good Lord! I had done it. I had telegraphed and maneuvered and mind bended and basically willed this to happen.

Working on the Night Moves

But then things were moving quickly, more quickly than I remember them moving in my youth. His hand was up my shirt. He was opening his door. Oh shit, I thought, are we going there already? I guess this is what grown ups do, get right past the silly games we played when we were new at this and scared of pregnancy and judgment.

I guess this is what grown ups do, get right past the silly games we played when we were new at this and scared of pregnancy and judgment.

“I have to tell you,” I whispered between kisses, “that I haven’t been with anyone but my ex for 23 years. And I’m terrified.”

“OK. Are you sure you want to do this?” he asked. (Wow! Good move. A man of my generation who thought to ask! He must have a good woman friend or a helpful sister.)

At this point I was too far gone to back out. “Yes, I’m sure.” Wait! Who said that?

He nodded as he took off my shirt.

I was amazed to find out that sex was pretty much how I remembered it. Yes, there was plenty of fumbling—where to put arms, legs getting stuck in awkward positions—but I recalled that this is normal until you learn each other’s bodies and patterns. When you’ve been married a long time, you pretty much know the drill—he touches this, you do that, he kisses you here, you stroke there—but with a new man there are a lot of surprises that you just have to roll with. Oh, you like that now? OK. Oh, this comes next? Well, why not?

I had to get used to new movements, the different sounds this man was making, his new smell, but none of it was unpleasant or scary in the least. Quite the opposite; it was thrilling. And I promise I didn’t think of my ex at all—except for one move my new guy made that was uncannily familiar but is too intimate to describe here.

The Sequel(s)

When we were done, we held each other for a long time, and when I felt his breaths lengthen and deepen, I figured I should let him have his bed back. Somehow, at this stage sleeping together felt more intimate than having sex. Before I left the room, he asked me if I’d come back at 7 the next morning. Then, I went next door—the shortest walk of shame ever. After texting my three friends and talking to one, I tried to sleep but I kept running every minute, every move through my mind. I felt truly liberated, as if I’d taken the first step to a new life one year post divorce.

We made it through the day, acting as if nothing had happened, when in fact EVERYTHING had happened.

I set my alarm for 6:45, but didn’t need it. I was up at 6 and after I showered, I tried to figure out what to wear. What would be alluring and still come off easily? I changed several times, then paced nervously. At 7, I didn’t leave; I thought I should be a little late. Not seem too eager. I decided to wait till 10 past, but at 5 past I couldn’t stand it any longer. When I knocked on the door, he answered right away but was half asleep. He was stretching and yawning in an old T-shirt and boxers—he obviously hadn’t been angst-ing over what to wear to our hook up. While he went to the bathroom, I stood around awkwardly, wondering if I should have come.

When he came out of the bathroom, he got right to business—this time with little preamble.

We made it through the day, acting as if nothing had happened, when in fact everything had happened. That mouth was just on my breast, I would think and try not to swoon. That hand was just….oh well, never mind.

That night, I made sure he came to my room. Something about that felt more dignified than for me to be tip-toeing to him yet again. We actually slept together that night, and it was a shock to wake up with one leg on top of someone else’s. I rubbed his foot with mine, and even though his breathing told me he was truly asleep, he rubbed his foot back, which made my heart leap.


After the conference was over, we had lunch together, just the two of us, and he told me he wanted to see me again. But Denver is far from my home in Pennsylvania. He told me he was busy until January, with the holidays and everything, but hoped we could visit after New Year’s. I knew that this could be just a line, that he could be letting me down easy. And as much as I really liked him, I was OK if I didn’t see him again. He had helped me over a barrier, helped me gain my sexual confidence—my mojo—and electrified an otherwise deadly snooze of a workshop (no easy feat).

But I got a text from him last night. He wants to come see me before Christmas.

Read More: Our Sex Survey Results Show That We’re a Pretty Randy Bunch. Good on Us!

A version of this story was originally published in December 2021. 

By Nicolette Stein


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