Saturday afternoon, I couldn’t breathe.

As I went through the motions of my day, all I could think of was the Media Club, and my impending doom.

Maybe I wouldn’t go, I thought. I was a busy man. I had things to do.

Being dragged behind a team of angry horses seemed, at this point, to be a particularly enchanting option.

I wasn’t ready. I could barely look a stranger in the eye for more than a second, let alone talk to them. I’d end up saying something stupid, and be slapped, or laughed at, or otherwise humiliated.

Bring $200 in twenties, he’d said.

This was the kicker.

I’ll admit it: I’m phenomenally cheap. I grew up poor, I hold onto my money jealously, and having to part with $200 for God-knows-what wasn’t exactly my idea of a rodeo. So, I sweated, and swore, and fussed, and worried, but in the end, I put on my best jeans and t-shirt, and headed out the door.

Four hours later, I was downtown.

DJ StrangeLove had insisted we meet at a nearby bar, to discuss strategy, and when I arrived, he was already on his third beer of the evening.

“You got the money?” he asked.

Reluctantly, I handed it over.

“Now what?”

“Now, we go out, and you approach 10 women. And for every woman you approach, I give you back $20.”

My heart started pounding.

“Great. So I just gave you $200.”

DJ StrangeLove poked his finger into the centre of my forehead.

“You’re not listening. I didn’t say anything about succeeding. You don’t have to take the girl home. You just have to talk to her.”

“And say what?”

I was starting to panic.

He sat back for a moment, thoughtful, and said:

“Beards.”

“What?”

“Yeah. You want to know whether you should grow a beard or not.”

He couldn’t be serious.

“So, I just go up and say: ‘Excuse me, guys-”

“Never start with ‘excuse me’,” DJ StrangeLove groaned, “it makes you sound like a homeless person. Also, never ask. It’s too easy to say ‘no’. Just walk up and say: ‘Hey guys, I need your opinion on something.”

“Right.”

“Then, ask your question.”

“And then?”

“Walk away. Kiss her. Punch her in the neck. I don’t care. That’s not the point. The point is just to start it. If you want to meet women, You have to meet them.”

He leaned forward, and touched me on the forearm.

I recoiled.

“You have a crazy-intense personal-space bubble, don’t you?” he remarked.

“What?”

“I leaned in, and you backed away. I leaned back, you leaned forward. It’s like a fucking see-saw.”

I laughed nervously.

“I guess. I just… I don’t touch people.”

He shook his head.

“Well, we’ll have to work on that.”

And then, we were out the door.

As we walked, DJ StrangeLove tried to keep me focused.

“When it comes to pickup, most people go in playing the ending. You want to sleep with a woman? You can’t go in with that objective. Before you sleep with her, before you kiss her, before you get to know her, you have to MEET her. Keep that in mind.”

I wasn’t keeping it in mind.

All I had in mind was to keep from crapping myself in the middle of Georgia Street.

We strolled into the Media Club fifteen minutes later, and the place was packed to the gills.

Even worse, it was a room full of hipsters.

The place was swimming in v-neck shirts and ironic facial-hair, the stage a contest over which band could wear the most radically different varieties of plaid without causing an explosion.

I looked at DJ StrangeLove in terror.

He winked.

“If you can start a conversation here, you can start one anywhere.”

I looked around in desperation.

“Don’t pick a target,” DJ StrangeLove shouted, “don’t think about it. You’ll just get nervous and fuck it up. If you’re going to start with anything, start with the closest.”

“Last time I was here, there were a bunch of dudes making out onstage,” I remarked, trying to stall him.

“Cool. Use it.

“What? But, it was gross.”

“Don’t say that. Say it was awesome.”

“But, it wasn’t.”

He slapped me on the back, harder than necessary.

“Look, it sounds counterintuitive, but a man comfortable making homoerotic comments is a man comfortable with his sexuality.”

“Won’t they just think I’m gay?”

He winked.

“Not once you have your cock inside them.”

My first approach was the girl from the coat-check.

Now, in my mind, this was cheating, since she had to talk to me, but, in the name of getting the ball rolling, I let it slide.

“Excuse m-” I said, and felt DJ StrangeLove’s elbow in my ribs.

She looked up.

“Should grow a beard, or what?”

“Um, what?”

She looked confused.

“Well, uh,” I said, floundering, “most of these guys have beards, and they’re, uh, having a good time. I figure-”

And, to my surprise, she screeched with laughter.

“Oh, definitely.”

“Well, thanks. Good to meet you. I’m Ian.”

She grinned, and we awkwardly shook hands.

“I’m Claire.”

And, just like that, we’d had a conversation.

The second approach was standing near the back. She asked if I was taking a survey or something.

The third was walking across the dance-floor, and, when I tried talking to her, fixed me with a withering look and continued on her way.

“You leaned in too far,” DJ StrangeLove remarked, “and pawed at her arm to get her attention. Don’t do that. It looks desperate. Lean back. Talk louder. Make her lean into you.”

The fourth was in the bathroom lineup. She laughed a lot.

The fifth was sitting with her friend by the dance-floor. They were so invested, they got into a debate, and started soliciting opinions from passers-by.

The sixth suggested sideburns.

The seventh recommended I shave my head altogether, just to be different.

To the eighth, I said:
“Hey, so my boyfriend and I were wondering: beard or no beard?”

She looked uncomfortable and walked away.

DJ StrangeLove grimaced.

“That wasn’t what I meant.”

Then, just as I was zeroing in on number nine, the show started.

I was stunned.

I’d been so focused on my objective, I’d totally forgotten that a band was supposed to be playing.

And, right there in a nightclub, too.

Amazing.

As they plodded their way through a variety of uninspiring hipster dreck, I felt my heart-rate decrease. I’d spent the last forty minutes in the grip of mortal terror, and, now that it was over, I couldn’t believe what I’d just done. Unfortunately, until the band was finished, it would be impossible to make another approach, and, in realizing this, I immediately lost what little nerve I’d had.

The show ended, and, as soon as it was over, the Hipsters cleared out remarkably quickly.

Within minutes, the place was empty, and with them, my last chance of getting my last $40.

Riding the train home, I was completely dejected. I had failed.

But, then, as I thought back, I realized that this was the largest number of strangers I had ever talked to in a single evening.

And, to my surprise, I was still alive.

I hadn’t been slapped, or laughed at, or otherwise humiliated.

On the contrary, everyone had been friendly, and polite.

I felt my confidence surge, and with it, the resolve to continue.

I would keep trying, I vowed.

I would get better.

And whatever DJ StrangeLove threw at me, I would do it.

That confidence lasted until exactly 11:00 the next morning, when I got my first “homework assignment”.