The big city just isn’t the best place to find your soulmate, evidently. The scuttlebutt I hear from single ladies in my circle is that most urban-dweller dudes just wanna play around, or our credentials (career, schooling, level of culture) don’t measure up to the ladies’, or we’re, ahem, married. Too, men and women tend to come to cities like New York, Chicago and L.A. with their own plans and schemes, which leaves romance at the bottom of everybody’s priority list. That said, the whole idea of friends with benefits—f’k buddies with no strings attached—seems to have become a lot more attractive in the past decade or so. Famously, it rarely works out without one side catching feelings; my experience was no different.

I first bumped into Chanté (not her real name) walking up a busy Manhattan ave on my lunch break back during my Vibe days “Hot girl,” I thought, admiring the amber dredlocks falling past her shoulders, and the deep dimples she flashed laughing on her cell. Fifteen minutes later, she was in my office asking for a job as my editorial assistant. It turned out we had an interview scheduled; moments after showing me her killer indie hip-hop ’zine and talking Nas to death, I decided the job was totally hers. Before I could put her on, all of a sudden I didn’t work at Vibe anymore (New editor-in-chief, new staff). As synchronicity would have it, fly Chanté walked right into the website music department of my next gig at BET looking just as sexy.

I had a weakness at the time for West End girls with ghetto passes, and Chanté was certainly that. Haitian and proud, Chanté palled around on the Upper East Side with actresses Chloë Sevigny and Liv Tyler, and took those smarts straight to Howard University. Chanté was downtown enough to kick it with the White girls she’d bum-rush New Kids on the Block backstage parties with, but down enough to fall in love with Hieroglyphics MCs like Souls of Mischief. We were fast friends, even with her boyfriend in the mix.

And then they broke up.

The dotcom bubble burst and most of us ended up laid off. Soon thereafter, my fingers were up Chanté’s skirt and snaking up her thighs in my Brooklyn apartment the minute the ex-coworker hanging out with us turned his back. Days earlier, she’d laid back on my couch (like many times before) watching Hype Williams’s Belly, but started stroking me stiff with the feet she planted in my lap. Kissing and fondling followed, along with the whole “what the hell was that?” moment. But we kept at it. Chanté and I never used the f**k buddy catchphrase, but we continued as homeys hanging without a romantic relationship on the table and plenty of satisfying, summertime-sweaty sex. Licking her salty skin after a day lounging away at Jones Beach was a highlight of whatever you wanna call what we were doing.

“I don’t understand what you could really see in me,” she told me eventually, evading the boyfriend/girlfriend issue yet again. Chanté had her share of (self-described) bipolar insecurity issues, but my BFF was quick to see through her excuses. “Her justification is to feed your ego. She just doesn’t want to be your woman,” he said. I started bringing Chanté her favorite Valrhona chocolate bread from Balthazar and other thoughtful little treats, but nothing changed her mind. Guys, of course, love a challenge, but when I started chasing, our sweet arrangement turned sour.

Like the unions of Ashton Kutcher and Natalie Portman in No Strings Attached, or Justin Timberlake and Mila Kunis in Friends With Benefits, the cliché tropes of f**k buddies-gone-wrong started to manifest. Sex once or twice with her ex didn’t bother me, but her sleeping with some third-rate rap producer definitely did. A true friendship with your partner is actually essential to any strong relationship, but we weren’t in a relationship, and she didn’t want to be. Chanté blurted out “I love you” one night during the best sex we ever had, then did a total about-face the next day. The whole thing was getting a little too complicated, she said. We should stop.

I did the denial bit—we had at least three “one last time” screws to wind things down. And there was resentment; I may or may not have childishly tossed a vintage blouse Chanté left over at my apartment. But before depression could set in, I went out to a BAMcafé concert and met Epiphany. And that was that. Coincidentally, Chanté and I both ended up marrying French spouses. We’re still genuine friends, and this whole months-long episode became a sort of running joke between us a long time ago. My friends-with-benefits flirtation turned out okay in the end, but it seems impossible to escape the problems that always seem to crop up without fail. (Ask anyone who’s been through it.)

Is sex between friends a good idea, or is it asking for trouble? Sound off!

Miles Marshall Lewis is the Harlem-based author of Scars of the Soul Are Why Kids Wear Bandages When They Dont Have Bruises, Theres a Riot Goin On and Irrésistible. Lewis is a former editor at Vibe, XXL and Follow MML on Twitter at @furthermucker, and visit his personal blog, Furthermucker.