When it comes to one-night stands, how many pros counter the cons of doing the deed? Sometimes a courtship culminates in one solitary sex session, a relationship doesn’t pan out, and you part ways. Maybe a friend turns into a friend-with-benefits just once, reverting back into a buddy right away. Those don’t count. A true one-night stand is that random stranger you manage to end up naked in bed with on one occasion only. Blame the full moon or that umpteenth shot of Cuervo Gold, but many of us have either slid down the rabbit hole with a Cheshire grin or woken up scratching our hangover-laden head. Are one-night stands good, bad, or just ugly?

Years ago in the go-go 1990s, I showed up to the birthday party of an ex (Zoë, in fact) and topped the night off making love to a beautiful stranger. Zoë and I had long broken up, but on friendly enough terms that I still made her birthday guest list. Her photographer friend from the Bay Area, the ex-husband of a top editor from Vibe, had shown up with “Raven,” an aspiring singer who didn’t seem to be giving him any rhythm. A milk chocolate sister with an aquiline nose and a huge dreamcatcher tattoo falling down the right side of her back, Raven had more and more to say to me as the night went on.

Seven of us split yellow taxis from an Upper East Side restaurant down to the Soho nightclub de rigueur. Raven rode with me, a harbinger of things to come. Our driver was a madman, almost pulling a pistol on another cabbie cutting him off on the F.D.R. Drive. After more drinks and a Tyra Banks sighting on the dance floor, some of us headed to the 23-hour hot spot Coffee Shop, our numbers continuing to dwindle. The photo guy took his Canon and bounced—Raven admitted trying to escape him—as I learned more about her. Already a twentysomething divorcée, she was born in Malawi and raised upstate and in California. Her passions included music, photography and activism. She’d traveled the world when her folks volunteered in the Peace Corps.

Raven had to ask me twice to skip work the next day before her over-my-head hints trickled down to my wine-addled brain. At three in the morning, we caught a cab together to Brooklyn. Thirty minutes later I tore the foil of a condom wrapper with my teeth and indulged in my one and only jumpoff. Funny how you pull out all your sexual tricks when you think there might not be a repeat performance; we both got our Kama Sutra on. Waking up the next morning wasn’t awkward at all. I called in sick; I showered; we spoke a lot about racism (Raven’s ex-husband was a white guy) and her local artistic mentors: guitarist Vernon Reid, photographer Chester Higginbotham. Then she went home.

Was the experience good, bad or ugly? Maybe none of the above. Given all the glasses of wine that night, I (unfortunately) barely recalled hoisting her crossed ankles over my shoulder or any of our other acrobatic pleasures. Raven slept over another night, but she wasn’t in the mood for another romp; I respected that. We went out dancing once or twice, and despite some serious dressed-sex grinding in the clubs, we both moved on.

Common sense says that men are more likely to brag about their one-night stands as badges of honor while women are often inclined to guard their reputations more and keep their exploits private. It doesn’t take a clinical sexologist to imagine that sex with strangers was rarer in the early 1960s of the Mad Men era than during the sexual revolution that immediately followed. No doubt AIDS slowed things down in the 1980s. Jumpoffs must’ve spiked again when Raven and I did our thing in the ’90s, as fear of STDs foolishly decreased again. After that, if famous folks are any representation of the general public, celebs like Brandy, Britney Spears and Reese Witherspoon all having babies at 23 reflected a kind of early maturation with Generation Y—not much time for one-night stands going straight from college to parenthood. Married and out of the running these days, I have little idea where things stand with jumpoffs and the ’10s.

Where do you stand on one-night stands? Would you? Could you? Why or why not? Speak, family, speak! 

Miles Marshall Lewis is a writer, editor and bohemian b-boy in New York City. Check him out on Facebook, follow him on Twitter:@furthermucker and visit his personal site.