My Attempt (and Missteps) at a One-Night Stand

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After over two years of involuntary celibacy following my husband’s departure after three decades of marriage, I found myself yearning for physical connection again. I wasn’t quite ready for a full-blown relationship—something I had always associated with sex—so the notion of a one-night stand, with no strings attached and perhaps no names exchanged, suddenly felt appealing.

This newfound desire coincided perfectly with my trip to Austin, Texas, for the South by Southwest (SXSW) festival, a renowned hub for music, film, and technology that also served as a hotbed for casual encounters. I had read about how SXSW could be described as “Spring Break for Adults,” where the thrill of potential success acted as an aphrodisiac. Attendees, with aspirations of becoming ‘Masters of the Universe’—a term coined by Tom Wolfe—might feel emboldened amidst the excitement. The warm Austin climate added to the allure, encouraging a relaxed atmosphere, while the endless supply of free drinks played a significant role in loosening inhibitions.

One of the key factors was the event’s setup; many talks took place in hotels, making them prime spots for spontaneous rendezvous. This was exactly what I needed to fill those awkward moments between presentations with some excitement.

I confided in a male friend about my mission, who surprisingly advised, “Look for a spark.” But if a spark existed, wouldn’t that contradict the very essence of a fling? I pondered whether I had the right look for my goal. At fiftysomething, I was in great shape but still packed my Spanx and skin-hugging outfits (though they looked a bit odd paired with sneakers). To prepare, I even treated myself to a waxing session before my trip.

At the conference, I made it a point to introduce myself to as many people as possible. I smiled, engaged in conversations, and mingled with younger men, attending various parties each night. Instead of burying myself in my phone, I made an effort to appear approachable, sipping on my Yellow Armadillo beer and imagining a glowing sign above my head that read “A-V-A-I-L-A-B-L-E.”

But, much to my dismay, I felt like an arsonist with a wet pack of matches—no sparks ignited. The most I managed were polite exchanges of business cards, which would inevitably end up crumpled in the laundry. I started questioning myself: Was it my appearance? Did I only seem “good for my age”? Why was I unable to enjoy the fleeting encounters that seemed accessible to everyone else at this moment in my life?

I reached out to my friend again, who suggested that men seeking one-night stands weren’t after depth, and despite my efforts to appear casual, I still exuded a sense of “substance.” (Good answer! I thought, whether it was true or not. Then darn it!). But how could I appear trivial enough to be considered a viable option for a one-night stand?

Upon returning home, I explored the “How?” of hooking up that I had overlooked earlier. It seemed I was supposed to be using dating apps like HowAboutWe.com. This was to be expected at a tech-focused conference, but where was the authentic human connection? Oh right: that was what I didn’t want.

I consulted a female friend who had fully embraced the sexual revolution of the ’60s. She described men today as timid and lazy, explaining that they no longer picked up on subtle cues since women had taken the lead in pursuing. This meant that dressing to highlight my assets and being open to opportunity was akin to waving a red flag in front of a blind bull.

She advised that today’s men desired clear signals, like prolonged eye contact, flirtatious smiles, close physical proximity, and engaging conversations. I realized I needed to adopt a much bolder approach to flirting—something I had forgotten during my lengthy marriage.

But the truth was, I couldn’t do it. While I believed I could separate my physical and emotional needs, I still longed for a connection that included conversation before and after the excitement. Why would I want to engage with someone who was indifferent enough not to want to get to know me? After feeling devalued in my marriage, a one-night stand would only amplify that feeling of worthlessness.

While I may have technically failed in my endeavor, I learned an invaluable lesson: my worth exceeds what I had been led to believe throughout my marriage. As I work to reshape my self-perception, I remain open to meeting those who value substance. So if you spot a woman of a certain age at a conference who seems unassuming, don’t hesitate to say hello and strike up a conversation—you might discover a connection that’s far more rewarding than you anticipated.

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In summary, while my attempt at a one-night stand didn’t pan out as I had hoped, it opened my eyes to my true worth and the importance of meaningful connections.