07/13/2012 09:50 pm ET Updated Feb 02, 2016

What Happened When I Hit On a Hot Guy... And Not on Grindr

I have never had a Grindr account. I have never answered a Craigslist personal ad (though I have found myself perusing the Missed Connections, just in case Anderson Cooper saw me on the N train and was too shy to say something. Don't be shy, Andy.). I have never logged onto Manhunt, or Adam4Adam, or any other such site. Please don't get me wrong, I don't judge anyone for their choices concerning their own personal relationships, phsical or otherwise, but I can't even get into the idea of Internet dating, let alone Internet sexing. To me, there is something oddly cold about the impersonality of the ever-increasing use of technology in dating/hookup culture. And perhaps that's the point; there is certainly an entire subculture of people -- gay and straight, men and women -- who are attracted to (or at least turned on by) the increased ease of casual sexual encounters. To me it just seems lazy. We can now quite literally use our iPhones and Blackberries to order in everything from dinner to drinks to hookups. Surely there is still something to be said for traditional methods.

I was thinking about this one recent evening after a particularly messy breakup, as I found myself drinking alone on a Tuesday night at the Cubby Hole, a cool little neighborhood bar in the West Village known for its super-strong $2 margaritas. After having a few drinks and chatting up a friendly lesbian named Carol who was sitting next to me at the bar, I glanced up just in time to lock eyes with a highly attractive guy ordering a drink a few feet away. I was probably staring for just a little too long, but he just smiled, took his drink -- a rum and coke -- and walked back toward his group of friends.

Now, if life were a romantic comedy, this would have been the part normally known as the "meet-cute." You know, the scene where Reese Witherspoon/Kate Hudson/Jennifer Aniston (or, if you're feeling nostalgic, Meg Ryan/Julia Roberts/Diane Keaton) has the slightly-awkward-in- an-endearing-way chance meeting with [insert hunky actor here], and everyone watching at home just knows they're going to end up together in the end. Unfortunately, most of our lives are not Hollywood rom-coms, and instead we find ourselves thrown into the dating world without a script or an audience rooting for us from their sofas.

The way I see it, we have a couple of options. We can either sit passively and wait for the right person to approach us, eventually realize it's not going to happen, and duck into a corner to sign onto to Grindr (not the greatest strategy), or we can take charge and be willing to "put ourselves out there," so to speak. It's a scary thing, definitely, to open yourself up to the possibility of being shot down, especially in a crowded bar. But as with everything in life, anything worth having is worth working for. It just so happened that on this particular night I was newly single and had built up a respectable buzz, so naturally I was feeling a little bold. I politely excused myself to my new friend Carol and made my way over to Mr. Rum and Coke.

At this point I should probably mention that meeting people in New York isn't exactly hard; they're all over the place. Meeting normal people is another story. Maybe it's all the rushing around; all those people constantly moving can make anyone a little neurotic. Or maybe it's the absolute ridiculousness of having 8 million people all cramped together. Whatever the reason, one thing is for sure: Whether you're gay or straight, meeting nice, dateable people in New York is no walk in the proverbial park (Central or Gramercy. Rimshot.). So sometimes you just have to be willing to take a chance, and I definitely had a good feeling about this guy. And as I approached, he noticed me coming and shot me another adorable smile.

"Rum and coke, right?" I asked, pointing at his drink. "How's the rum here?" (Sidenote: When you put yourself out there, sometimes you will say completely stupid things like, "How's the rum here?" Chalk it up to a learning experience and move on.)

"Not bad. I saw you at the bar. Are you here with friends?" he asked.

"Yeah," I said, motioning my glass towards Carol, who was now deep in conversation with some girl who had taken my seat.

And so it began. Fifteen minutes later we had both ordered a fresh drink and were deep in conversation. I'd learned that his name was James and that he, like me, had grown up in the South and liked puppies. Things in common!

"So what's your story?" James asked during a brief lull in the conversation. "Are you single?" This guy was moving fast. And I kind of liked it. Not to get all Sex and the City, but that's the thing about putting yourself out there. Sometimes it's totally life-in-the-fast-lane.

"Yeah," I said, leaving it at that. I briefly considered telling him the whole story of my breakup and my evening drinking cheap margaritas by myself, but fortunately I wasn't quite drunk enough to lay all that crazy out on the table.

As we were finishing our drinks, James' phone started buzzing. "It's my friends," he said, checking the screen. "They're outside waiting for me. Listen, I have to run. But if you get bored here, you should call me and come meet up." And then he reached into his pocket and pulled out a business card. I kid you not.

"OK," I said, taking his card. His card. Classy.

And with that, he flashed yet another cute smile and walked off.

I stood there for a moment, a little unsure of what exactly had just happened, but feeling pretty good about myself nonetheless. Had an attractive, seemingly normal guy just given me his number? I looked down at the card. Ten perfectly printed digits, followed by a name: James. No last name, just James. And then, under that, typed in bold font, two more words: Male Escort. And his rates.

Now, if life were a John Hughes film (and if I was Molly Ringwald circa 1986), this would be the part where I covered my face with my fashionable, homemade handbag and hurried to the bathroom before anyone noticed my face flushed with embarrassment. But I didn't. Despite the outcome, I felt pretty OK.

In this crazy world where impersonal tools like Grindr and (God forbid) Craigslist all too often replace real, human connections, I had swallowed my pride and hit on a hot stranger, which had given me the confidence to do it all over again next time, and I hadn't even so much as glanced at my Blackberry. That, to me, is a victory in itself. This is how meeting people is supposed to go. We stumble along the way, we end up with a few crazy stories, and eventually we get back up and do it all over again until the odds finally tip in our favor. It's all about the journey. Think about that the next time you find yourself tempted to give in to the ease and accessibility of handing over your sex life to an app.

Just be aware that "putting yourself out there" also means opening yourself up to the possibility of rejection and/or rentboys.