How I Tried (and Failed) to Have a One-Night Stand

I had been involuntarily celibate for more than two years—ever since my husband left me after over 30 years of marriage—when I began to feel a desire for physical intimacy again. I knew I wasn’t ready for a “relationship,” which I’d always considered a prerequisite for sex; in my still-vulnerable state, such a connection only risked more pain. For the first time, the idea of having a one-night stand—sex without commitment, possibly without even knowing each other’s name—seemed like a great idea.

Conveniently, this desire surfaced shortly before I headed to Austin, Texas, to speak at South by Southwest (SXSW), the annual music, film and technology conference that was also a notorious hookup venue. I read about the phenomenon and learned why South by Southwest might alternately be called Spring Break for Adults.

One explanation was that prospective success was a powerful aphrodisiac. Some of the interactive, music and film attendees of the conference might, some day, become “Masters of the Universe,” as Tom Wolfe once dubbed Wall Street bankers at the height of their powers. At South by Southwest, those future Masters had egos only as large as their daily ATM withdrawal limits.

The heat of Austin was also credited with encouraging people to shed their clothing, but more likely, the abundance of free alcohol encouraged people to shed their inhibitions.

The best explanation, however, may have been that many of the talks were held in hotels—convenient locations for “nooners” or any-other-time-of-day-ers. Plus, being out of town eliminated the potential awkwardness of running into an intimate stranger. All this made casual sex seem like regularly unscheduled events, a practical way to fill in those awkward time slots between presentations.

I shared my nervous goal with a male friend who urged, surprisingly: “Look for a ‘spark.'” (But if there were a “spark,” wouldn’t that negate the definition of a fling?)

Of course, I wondered whether I looked the part to pull off my objective. At fiftysomething, I’m in very good shape, but I packed my Spanx and some body-conscious clothing (that, admittedly, looked a little silly with the requisite sneakers for running from one venue to the next), set my mind to be open to possibilities, and—so as not to sabotage myself with a last-minute change of heart—got waxed before heading to Austin.

Once at the conference, I took every opportunity to introduce myself. I smiled; I was friendly; I initiated conversation. I spoke to a lot of younger men (almost all of them were younger). And every night, I attended at least one of the many parties that were always going on. At these gatherings, I didn’t fix my gaze on my iPhone or try to look like I was working importantly on my iPad. Instead, I glanced around as I sipped my Yellow Armadillo beer while imagining a sign above my head flashing: A-V-A-I-L-A-B-L-E.

But like an arsonist with a wet pack of matches, there were no “sparks.” Nothing went further than the obligatory exchange of business cards that were shoved into back pockets, only to be withdrawn, if at all, before tossing the jeans into the wash.

Where had I gone wrong? Did I not look good, but only “good for my age”? Why couldn’t I enjoy an experience that seemed available to everybody else at the one time in my life when I was receptive to it?

I contacted my friend again. He explained that men who looked for one-night stands weren’t looking for substance, and no matter how much I tried not to seem like a serious person, I still radiated “substance.” (Good answer! I thought, whether it was true or not. Then Darn it!). But what did I need to do to seem trivial enough to be taken seriously as a one-night stand candidate?

Upon returning home I explored the “How?” of hooking up that I had neglected to study earlier. Apparently, I was supposed to have gotten wired into one or more of the dating apps, such as HowAboutWe.com. Perhaps I should have expected that from a technologically oriented conference, but where was the human connection?

Oh, right: That was what I didn’t want.

I contacted a female friend who’d thoroughly partaken of the sexual revolution of the ’60s. She explained that men had become—what was her word? Timid. And just plain lazy. They no longer needed to pick up on subtlety as women had become the pursuers. Which meant that dressing to highlight my assets and being receptive to opportunity was the equivalent of waving a red flag in front of a blind bull.

What men today expected, she explained, was the equivalent of an engraved invitation: sustained eye contact, a seductive smile, invasion of their personal space with physical contact, and provocative conversation. I needed to become much more aggressive and actively flirt, which, had I ever known how to do, I had forgotten during my long marriage.

I couldn’t do it. While I thought I could separate physical from emotional needs, I still pictured having someone to talk to before our heart rates sped up and after they slowed down again. Why did I aspire to hook up with someone who thought so little of me that he didn’t want to get to know me? Having been devalued in my marriage, a one-night stand would have only diminished me further.

While I technically failed in my goal, I learned, instead, to listen to what the people who know me best have been telling me for years: that my value is much greater than what had been communicated to me during my marriage.

While I try to internalize a new perception of myself, I remain open to meeting people who care about substance. So if you see a woman of a certain age at a conference who is not trying to draw undue attention to herself, say hello and try to get to know her. You might get lucky in a different way than you had expected.