I spent most of last week with Rob Barnum, a new hire who’ll be managing the West Coast office of Cyan Pictures + Long Tail Releasing, who was in town to get up to speed on both companies. While still in college, Rob served as an exec at EscapeHomes, helping to take the company through several large venture capital rounds and a recent merger. He then started a production company to escape from the world of tech and into the world of film. Plus, he screenwrites, and blogs, and drinks heavily.

So, in short, I hired him because, in true narcissistic style, I like people like myself.

It wasn’t until Friday night, however, that I realized how dangerous having both of us in the same room would be. Because Friday night, we headed down to the West Village, hit the first crowded bar off the subway steps, and decided it was imperative that we spend the evening picking up random women.

Now, picking up women in bars is a chump’s game. It puts you into competition with every single other guy in the bar. Worse, it puts you on par with every single other guy in the bar, makes you the sketchy sort of guy who spends Friday night hitting on random women.

Sure, the girls are ostensibly there because they want the attention, having layered on makeup and cocktail dresses. But, deep down, every girl would much rather date a guy she’d met at the park or through a friend or in the yogurt aisle of the supermarket. The Fat Black Pussycat just lacks tell-your-grandkids-about-how-you-met charm.

So, if you’re looking to meet women at a bar, the main thing is to not be like all of the other sketchy guys surrounding you. You’ve got to be different, in a good way. You’ve got to think outside the booty box.

Rum and Coke’s in hand, Rob and I sat down at the first bar to discuss that conundrum, and to scope out the options. To our immediate right was a group of three girls, sitting together, dutifully brushing off a chain of successive hopefuls coming over with their smoothest entrances. They seemed as good a choice as anyone else.

Before I had the chance to reason my way out of it, I excused myself from Rob and headed over. “I’m sorry to interrupt,” I said, receiving icy stares. “But I was wondering which you think are cooler: blimps or hot-air balloons.”

“What?”, one of them asked.

“Blimps or hot air balloons – which is cooler. You.” I pointed to the one in the middle.

“Blimps, I guess,” she said, slightly confused. I got another blimp vote, then one for hot-air balloons.

“Thanks,” I said. “That’s all I needed.” I walked back to Rob, sat down, and checked my watch.

Thirty-four seconds later, the most intrepid of the three walked over.

“Now we’re curious,” she said. “Why did you want to know that?”

“It’s not that important,” I replied, and went back to talking with Rob.

“You can’t just ask us that,” she continued. “You have to tell me why you wanted to know.”

“Well,” I started, then looked to Rob, who nodded approval. “We’re going to be racing from New York to Chicago. Either in blimps or hot air balloons, and we wanted to see if one was cooler than the other.”

“Racing to Chicago?” the girl asked, dubious.

“Well,” Rob jumped in. “My grandfather passed away recently, and gave me an old hot-air balloon in his will. I was thinking about repairing it, and then I thought, if Josh buys one too, we could race.”

“Right,” I continued. “But I figured Rob could probably get some trade-in value on the balloon if we wanted to switch to blimps and race those instead.”

Rob and I nodded nonchalantly, like that pretty much summed it all up.

“You have to come with me to tell that to my friends,” the girl said. We were in.

Over the course of the evening, at several bars and with several groups of women, we worked our way through variations on the theme. Perhaps Rob was going to be in a hot-air balloon and I’d be in a blimp, and did they think that would put one of us at a disadvantage? Or, we had already bought the blimps, but we were in town to see if Blimpie would be a corporate sponsor of our race.

While we’d come in totally deadpan, we tried to slowly edge the story over the top, to let the girls in on it. The good ones got it, and played along, happy to be inside a shared joke. The slower ones never seemed to catch on, but remained credulous and interested.

Either way, after a while, we’d excuse ourselves, bow off invitations to join them at subsequent bars, decline phone numbers. We weren’t really there to pick up women. We just wanted the thrill of the chase.

Which, I would guess, is almost as exciting as racing hot-air balloons.