How To Talk To Armed Policemen, Part Two: Up Your Game

‘I really like your fashion sense.’

What do junior-level chess players have in common with pickup artists? This isn’t a trick question.

Once, for a thing I was writing, I spent a couple of weeks hanging out (online and In Real Life) with a group of self-proclaimed pickup artists. I’m not going to make generalizations about them: some were nice but shy, some predatory to the extent that I wanted to punch them in the face, some genuinely just wanted to get better at talking to girls and some wanted notches on the bedpost. How successful were they? We’ll get to that in a second.

More recently, I read Josh Waitzkin’s Attacking Chess, a book well worth ploughing through even if you don’t care about pawn storms or the concept of zugzwang. In it, Waitzkin discusses the problem with memorising openings. There are plenty of superficially good reasons to memorise openings – every game starts with them, they’re a good way to get an early advantage against inexperienced opponents, and having a tricky King’s Indian variation in your arsenal is a great confidence builder. The problem is that they go on forever: there are entire books full of them, with new ones being invented all the time. You could spend your life learning new ones, but it still wouldn’t give you the deep understanding of chess fundamentals that it takes to be a genuinely great player. Ultimately, argues Waitzkin, you’re better to learn the principles that will get you through the opening in a fairly decent position, rather than relying on a set of rote traps that do nothing for your long-term chess improvement.

This, obviously, made me think about talking to people.

If you’ve got ten minutes and a Private Browsing option on your computer, check out one of the big pickup forums. You’ll find hundreds of ‘openers’, routines, ‘foolproof’ lines and other canned dialogue that will probably make you feel uncomfortable about the whole thing. Some are good, some are bad, some are face-palmingly awful. They mostly follow the same theme, which is that they’re an innocent-sounding thing that can spark up – or continue – a conversation, and some of them definitely work. But the thing is, just like memorising the Queen’s Gambit or the Sicilian Defence, saying the same thing to every person you meet isn’t going to help you talk to anyone in the long run. You could memorise a thousand of these lines, and all you’d be is a Turing machine (you know, like Cleverbot) firing out predetermined conversational strings with no intelligence behind them.

This was the problem with some of the pick-up artists, one of the few sub-sets of the population who actually make a genuine effort to improve their conversational skills. They’d go into bars starting conversations with ‘Quick question: is it cheating if my friend’s girlfriend kisses another girl?’ or ‘I need your opinion: does my friend look like a drug dealer?’ but then they’d be reduced to firing out more and more pre-memorised ‘quick questions’, with nothing original to say.

Now: most pick-up artists will tell you that these ‘openers’ are supposed to be training wheels which you eventually take off, but to get better at talking to people, I think there are better ways: ways that don’t leave you relying on your ability to memorise canned lines.

Here’s one: next time someone asks, ‘How was your day?’ don’t just respond with a tired ‘Fine, I guess,’ or ‘Okay, I didn’t do much.’ Instead, make it your mission to tell them an engaging little anecdote about how your day *actually was*. It doesn’t matter if your day was exciting: something happened that was interesting, that helped you reflect on who you are, or how you can get more excellent as a person. You’ll find this tough at first, so use the days when nobody asks to work on the skill yourself. Example days I’ve had where ‘nothing happened’ include:

‘Nice. I saw a really heartwarming thing at the train station; there’s this one station attendant who always notices when couples are seeing each other off, and lets the person who doesn’t have a ticket through the barrier. It makes people really happy. I love it when people step outside the boundaries of their job to make people’s lives a little bit better.’

‘Dreadful. I got all over-excited in the gym, did too many squats, and then I had to lie on the sofa feeling sick for most of the afternoon. On the plus side I only really feel like I can binge-watch TV when I’m physically incapable of doing anything else, so I managed to catch up on Breaking Bad.’

‘Worrying. I was walking through the park and I saw a badger. Aren’t badgers supposed to be really vicious? I’m basically more scared of badgers than muggers, at least I know how to fight muggers. I don’t know any self-defence moves that work against traditional badger attacks.’

The point is that you don’t need a wildly exciting life every single day: that’s not possible. Instead, you need to think about the world in a way that lets you talk to people about your feelings and values without sounding like you’re reading from a script. Because then they’ll talk back.

HOMEWORK: For the next five days, whatever you do, sit down – with a notebook if it helps – and work out how to tell an interesting anecdote about what happened, good or bad. How was your day? Probably more interesting than you think.

About the author


Editor and creator of Live Hard. Fighting enthusiast, steak lover and aficionado of all things self-improvement related.

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