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How I Attempted (and Stumbled) on a One-Night Stand
After being unexpectedly single for over two years—thanks to my husband leaving me after three decades of marriage—I began to crave physical closeness again. I realized I wasn’t ready for a full-blown “relationship,” which I’d always thought was necessary for intimacy; that kind of emotional connection felt too risky in my still-fragile state. For the first time, the thought of a one-night stand—sex without strings attached, possibly even without knowing the other person’s name—sounded appealing.
As luck would have it, this desire hit me right before I traveled to Austin, Texas, to speak at South by Southwest (SXSW), an event famous for its music, film, and tech happenings and notorious for casual encounters. I’d read about how SXSW could easily be dubbed Spring Break for Grown-Ups.
The buzz around the conference suggested that the thrill of potential success was a huge turn-on. Attendees, some of whom might one day be industry titans, strutted around with egos as inflated as their ATM limits. Sure, the heat of Austin played a part in people shedding their clothes, but let’s be real—the free-flowing alcohol was likely the main culprit for loosening inhibitions. Moreover, the fact that many sessions took place in hotels made it easier for spontaneous “meet-ups,” freeing attendees from the awkwardness of running into someone they’d just hooked up with later on. All this made casual encounters seem like a normal part of the event, filling in those awkward gaps between panels.
I shared my somewhat anxious goal with a male friend, who surprisingly advised me to “look for a spark.” But if there was a “spark,” wouldn’t that contradict the whole idea of a fling? I found myself questioning whether I looked the part for this endeavor. In my fifties, I’m in decent shape, but I packed my Spanx and fitted outfits (which admittedly looked a bit silly with the sneakers I wore for running between events). I even took the precaution of getting waxed before heading to Austin, determined not to sabotage myself at the last minute.
Once at the conference, I made a point to introduce myself to new people. I smiled, engaged in conversations, and focused on meeting younger guys (most of whom were indeed younger). Every night, I hit at least one of the many parties happening around the venue. Instead of burying my face in my phone, I scanned the crowd while sipping my Yellow Armadillo beer, half-hoping for a sign that read A-V-A-I-L-A-B-L-E above my head.
But like a firestarter with soggy matches, I found no “sparks.” Conversations fizzled out into mere business card exchanges, quickly forgotten in the depths of back pockets, only to be lost in the laundry. What went wrong? Was it that I didn’t look good enough, just “good for my age”? Why couldn’t I enjoy the experience that seemed so readily available to everyone else, especially when I was finally open to it?
I reached out to my friend again, and he explained that guys looking for one-night stands often didn’t seek any substance. Despite my best efforts to appear nonchalant, I still apparently radiated “seriousness.” (Great answer, I thought, whether it was true or not. But still! What did I need to do to seem trivial enough to be a viable one-night stand candidate?)
When I returned home, I dove into the “how-to” of casual hookups I had overlooked before. Apparently, I was supposed to be using dating apps, like HowAboutWe.com. I should have anticipated that from a tech-heavy conference, but where was the human connection in that? Oh, right—that’s not what I wanted.
I consulted a female friend who had fully embraced the sexual revolution of the ’60s. She told me that guys had become—her word? Timid. And lazy. They no longer picked up on subtle cues since women had taken the lead in pursuing. So, dressing to accentuate my assets and being open to opportunities was akin to waving a red flag in front of a blind bull.
What men were looking for now, she said, was essentially an engraved invitation: prolonged eye contact, a sultry smile, invading their personal space with a light touch, and flirty banter. I needed to be more aggressive and flirtatious, which was something I hadn’t practiced during my long marriage.
In the end, I couldn’t bring myself to do it. While I believed I could separate physical and emotional needs, I still envisioned needing someone to converse with before and after things heated up. Why would I want to connect with someone who saw me as just a fleeting moment? After being devalued in my marriage, a one-night stand felt like it would only diminish me further.
So while I didn’t achieve my goal, I learned something important: my worth is far greater than what I’d been led to believe during my marriage. As I work to internalize this new self-image, I remain open to meeting people who value depth. So, if you spot a woman of a certain age at a conference who isn’t trying to draw attention to herself, say hi and maybe get to know her. You might find a connection in a way you didn’t expect.
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Summary
In her quest for a one-night stand after years of being single, the author reflects on the challenges of casual encounters in a modern context. Despite her efforts at a tech-savvy conference, she learns that her deeper emotional needs and self-worth may be at odds with fleeting connections. Ultimately, she gains insight into her value and remains open to meaningful interactions.