In 2008, I resolve to hit the bar scene and get my flirt on. I know it’s unlikely that I will find the man of my dreams. I know it’s improbable that I will even find someone to date. But I want to prove to myself—someone whose previous best pick-up move was dancing yards away and giving the desired subject occasional glances, wishing and hoping and telepathically-directing oh-so-hard that he’d turn in my direction—that I can actually do it.

I began the year’s challenge in perhaps the most difficult of places to start: South Beach. In Miami, the club scene pulses, but it’s the men within them that make the heart twitter: Tanned, muscled arms, squeezing out of fitted designer t-shirts, worn by naturally-olive-skinned gods who sport sunglasses atop their perfectly-molded hairdos. Every romantic accent spews from all directions: Spanish, Italian, Portuguese… even Jude Law British. Walking into a Miami Beach club is like strutting onto a runway where good-looking wannabes distinguish themselves from the real models by gawking at them. For the actual hotties, this crowd is the standard. It’s perfectly normal. Everyone else is just a tourist.

I was, of course, a tourist. And as I sat in an artsy hotel restaurant, wearing my not-good-enough-anymore Banana Republic blazer and DKNY white button-down (both purchased on clearance), I attempted to polish my flirting methods with my friends.

“It’s a crowded club,” I pitched to them, “and I have to get someone’s attention. What do I do?”

My friend Ashley looked to my eyebrows. “Can you raise them?” she asked.

I raised them.

“Not as surprised-looking,” Jen, another friend, directed.

I raised my left eyebrow, slightly and quickly. I met a chorus of oohs and aahs.

Ashley continued: “Now before you do that, give me a look—down and then up my body, like you’re checking me out.”

I glanced at her down, and then up, as told.

“Too quick,” she denounced. “You look like you’re about to fight me.”

I tried it more slowly. I scanned her body more smoothly, past her neck, breasts, and abdomen, down to the zipper of her pants, where I paused before trailing my eyes back up her stomach, chest, chin—and then her eyes. I capped the advance with my previous move: the lift of my left eyebrow.

“Yes, that’s good!” they cheered.

Excited by my progress in Flirting 101, I asked them for my next steps. “So then what?” I pushed, “Do I just wait until they approach me? Do I approach them? Do I smile?”

“No,” Ashley interrupted, “Don’t smile.”

“Why not?” I had always been told that people in clubs want to see others having a good time. (Thus the attraction, I’ve been told, behind the lone clubber, breaking into his solitary groove on the dance floor. “It’s mysterious,” others are supposed to think. “How can he be having so much fun alone? I guess I should find out…”)

“It can look sketchy. It’s… it’s… not seductive.”

Seductive? In my head, I had always thought of flirting in two ways: there’s making yourself seem so interesting that the other person demands to find out more about you, and there’s oozing sexuality with every look, step, and gesture you make (so much so that you could make a man follow you out a club without even trading words). One of them makes you a whore. A lucky one, but a whore nonetheless. I wasn’t going for whore.

Indeed, why would I be trying to be anyone else but myself? Why wouldn’t my music-loving, lights-entranced, alcohol-induced ass not be smiling and having a good time at a club? I’m a generally serious person when it comes to getting work done, but who wants to dance with an office drone? If I tried looking seductive, I’d be misperceived as being downtrodden and blue. Maybe drunkenly so. I had to let my lighter side show: A smile, a sparkle in the eyes, the Cabbage Patch on the dance floor. I decided to set aside my down-up-eyebrow move for the night and be—well—me.

Being me, apparently, does not cut it on South Beach. Three hours later, inside a club near Lincoln Road, I was dancing the night away with my girls, each of whom—surprise, surprise—had already paired up with an unassuming straight foreigner who had somehow found himself at Gay Night. I, on the other hand, had paired up with an ottoman atop which I decided to stand and dance. (I’ve danced atop chairs, tables, and counters in eight states and two countries.) And while I had my drink in my hand, a smile on my face, and my groove to boot, any visual or physical contact I attempted to make seemed to fall short of whatever it is that people wanted instead. A guy looked at me and turned away. A guy looked at me and then turned to my girls. I thought that the one guy who I had the courage to speak to was straight. It turned out he wasn’t. “I’m not straight,” he uttered in the most straightforward assertion I’ve heard in a while. He gave me the down-up look—the awkward, challenging one—and continued dancing elsewhere. Oops.

So what is it? Do people really want to be seduced? Or do they want to see you having fun? Should I even think about flirting from this perspective—that is, from thinking about what others want? Or should I forego the personal manipulations and be, plainly, me? Ideally, that’d be the easy answer. In reality, I may have to play the game.