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Trying to Appear Cool on a Date

01/08/2013 11:24 BST | Updated 30/09/2013 10:12 BST
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When I think of my recent attempts to appear 'cool' I feel remorseful - even my usage of the word puts me out of the game. Growing up in a working-class household in south London, I was surrounded by earthy culture and rough characters. I spoke, as we all did, in an arcane vernacular that was impenetrable to most adults, and indeed, the middle-classes. Prowling the midnight streets, we owned the city, albeit its least desirable enclaves.

Years later, I moved into the professional world. As I toiled the sanitised furrows of the HR function, and noticed the classes living cheek by jowl, I felt the need to change. I did this by modifying my speech. Other than a cursory knowledge of wine, this is the surest sign of breeding. As my vowels fluctuated, so too did my affectations. Within a decade, I had morphed from hooded youth to corporate gent. During the course of this shift, I had lost every ounce of urban grit. I became the thing we had mocked at school - posh.

It was a Friday night, and I was on my way to an Internet date in Brixton. I remember it as a desperate place, but it's fine now, even Foxtons thinks so. As I stood in the bus shelter with my Budgens All-Day Breakfast sandwich, I felt a melancholic twinge. I had been here my whole life, and yet, the place was unrecognisable. I put on my headphones and played Jay-Z's 99 Problems. The familiar guitar riff sounded and I nodded along, my face fixed in a steely thousand-yard stare - pausing only to pick the cucumbers out of my snack, I felt ferocious.

At Brixton, I saw Anna by the station, she had that Brixton look - consciously nonchalant, despite the questionable characters.

"Hi there," I said, weaving past a barefoot man.

"Hello," she said, "lovely to meet you at last."

I gave her a single peck on the cheek. The greeting-kiss was problematic, Londoners have yet to reach a consensus on whether it's the single or double. Anna expected a double, but I pulled away.

"Let's go somewhere nice," I said, motioning down the road, feigning familiarity.

"But this is nice," she said.

I scanned for signs of irony.

"Yes. This is, however, the street."

I smiled but she looked ahead.

"Where do you suggest then?"

I pointed to the Ritzy cinema - with it's excessive use of chalkboards and faux-rustic styling, it was the local hipster-magnet.

After a few drinks, we settled into a rhythm. Anna was straightforward and open with a look not dissimilar to Anne Hathaway. If Anne Hathaway were slightly overweight. Supping from plastic glasses, we battled to convey our humour - something so abundant online was not so forthcoming in person. The Internet affords us the time to construct our quips, real life is not quite so convenient.

She said, "I hate the way that online dating has been packaged as some kind of comedy of errors. It's like we're slightly embarrassed about it, so we try to palm it off as a joke when things go wrong."

"I suppose."

"It's like those blogs where they bang on about their dating disasters."

"I suppose they like the alliteration."

"You're funny," she said.

"Thanks, I think. Listen, why don't we get out of here? I know a place down the road where they've got a great sound-system."

I considered saying 'wicked' sound-system, but was unsure of the term's currency. I was also reluctant to endorse a place I had only googled that afternoon.

We rounded a corner and stepped into Brixton Market.

I said, "I remember this place back in the day."

"Sorry?"

"The day, back in the day. The old days."

A white man with dreadlocks stepped in front of us.

"Dance tonight," he said, holding out a flyer.

"No, thanks."

I turned to Anna, "you don't fancy dancing, do you?"

"No, he means it's a Dance, you know, a club night."

"I knew that, actually, it's been a while since I mashed it up at a dance. What do you think?"

"I don't know."

"Can I have one, mate?" I said to the man.

Two bearded youths passed, taking flyers without breaking their stride. The man looked down the street.

"Excuse me," I said, "I would like one of those."

He said, "actually, I don't think you'd like it."

"I'll be the judge of that," I said, holding out my hand.

Anna pulled my sleeve.

"Just leave it," she said.

"No, I will not. Sorry, but this man is an employee of the..." I turned my head to read, "Mast club, no, Mass club. And he is turning away business."

He flicked his dreads over his shoulder, and took a step back.

"What tunes are you playing?" I said, raising my voice.

He shook his head and turned away.

"Ridiculous," I said to Anna.

"Isn't it just. Shall we go to this place you mentioned? I am sure you can mash it up there."

I turned with a smile, but she was looking into her phone.