Nearly everyone who lives in a major metropolitan area has an acquaintance who’s had sex with someone rich and famous. Author Karrine Steffans branded an entire cottage industry out of it. Whether basketballer or MC, crooner or thespian, celebrities legendarily have no problems getting laid. And except for that Behind the Music episode on Eighties’ all-girl new-wave band The Go-Go’s, there isn’t much evidence that female stars take advantage of their fame for bedroom benefits like the guys do (it’s impossible to imagine Nicki Minaj trolling a nightclub for a groupie to go downtown on her; Lil Wayne, not so hard.) But when it comes to the politics of sleeping with the stars, what’s at stake? Self-respect? Reputation? Dignity?

Amber Rose publicly passing through a relationship with Kanye West to get engaged with Wiz Khalifa raises eyebrows in certain circles, yet everybody is someone else’s ex, famous or no. New York City is the most densely populated city in the country. But despite the teeming number of singles here, guys with the fortune of dating some of the five boroughs’ finest, most intelligent and ambitious young ladies inevitably end up courting some celebrity’s former flame. Stars are constantly on the make, and why should the sexy Spelman grad date the UPS guy when Drake asked for her number last night?

Sans exaggeration, I’ve personally gone out with NYC women who’ve collectively been with at least 10 different celebs: John Singleton, Prince Paul, DJ Premier, Black Thought, Wyclef Jean, MC Hammer (yes, MC Hammer), Dr. Dre (the heavy one), etc. And I don’t attract groupies, at all. I was just lucky enough to get involved with brilliant beauties, and celebrities’ exes are all over the place. It all just goes back to that hot Spelman alum with Drake’s number in her iPhone—she can, so she does.

My guy peers in music journalism may have flirted with their share of celebrity skin over the years. But let’s get real: Rihanna is not gonna do the editor, even for the cover. Yet Snoop Dogg might try, if the editor’s a woman. Male writers were quick to point fingers accusing female music writers of possibly maybe sleeping with an MC or two back in the halcyon days of hip-hop journalism, wholly without admitting that we certainly would if we could too.

Case in point: my date with Mariah Carey. Circa 1997, a minor trend coursing through women’s magazines involved sending writers on “dates” with celebrities: a night out on the town with Tyson Beckford, for example. With the “Honey” single topping the pop charts, Honey magazine called offering $300 petty cash to take curvaceous, 28-year-old Mariah Carey out to the upscale Tribeca restaurant Mr. Chow and see what happens. She was newly single; so was I. A perfect match, give or take $500 million.

Before the D-day, I dreamed of her emerging dripping wet from a swimming pool in the gold bikini from her “Honey” video over and over.

But at Mr. Chow, I kept things charming. The only celebrities to really throw me off are people like Run-DMC or Spinderella, folks who were famous when I was a wide-eyed teenager. Mr. Chow is so chic that there are no menus; Mariah and I ordered whatever choice Chinese food we were in the mood for with a $150 bottle of Bâtard-Montrachet burgundy wine. She was a good, giving and game Long Island girl, conversational and amused with the farce of the night as we continued to get sauced.

Her driver circled us through Central Park before heading for Brooklyn, dropping me off at my brownstone. I leaned in for that European corner-of-the-mouth peck, but we somehow ended up with something different for Honey to splash across the page of my story: a full-blown French kiss. She drove off and I stumbled to my apartment like a Tom and Jerry cartoon, heart pounding, all valentine-eyed. I left a few messages with her publicist (I had to try, right?), but never saw nor heard from Mariah again.*

Sleeping with celebrities is fraught with obvious challenges. Fidelity tends not to be a high priority for them, for one. Most women tend to fear negative judgment from their friends, or judge themselves too harshly to be a jump-off for a famous guy liable to forget their name in the morning. And some, of course, go there anyway. But can you blame a girl for sleeping with Usher if you’d gladly twist Cassie Ventura into a pretzel between the sheets given the opportunity? And anyway, is it really any of your business if she does?

*Our hero has never eaten with Mariah Carey at Mr. Chow…April Fools!

Have you ever had a close encounter of the romantic kind with a celeb? How did it work out? If you had the opportunity to kick it to a star, would you go for it? Or would you be too afraid of looking like a groupie? Speak on it! 

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.