‘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.

Paulo was 50, and he ran the BJJ academy I was staying at – he didn’t practise himself – and he reminded me of my grandad a bit, and he was the most charming man in the world. On the day he met me at the airport, he screeched into a petrol station and honked at the attendants and nearly ran one of them over, and then by the time he left, they were all be laughing and waving at him like they were sending an old friend off on a round the world trip. My Portuguese wasn’t up to much at the time, so I don’t know what he was saying, but it worked. And he would do this with everyone – friends, relatives, people in surf shops, the men who sell fresh coconuts out of little huts on the beach – he could make anybody laugh, and get things cheap, and get things done.

Anyway: one fine day, we were on our way to see the big Jesus, slightly lost, trying to read a map and there was a police car in front of us. There was also a barricade, and a load of young chaps wandering around in what might have been gang colours. Inevitably, the police car pulled up, flashed its lights, and all the men in it – in plain clothes – leapt out, waving guns. One of them – who looked a bit schoolteachery – has a machine gun. And instead of doing what I´d have done on my own – squealing and hiding under the seats – Paulo pulled up next to him and asks for directions. And unbelievably, the guy lowered his gun, smiled and stopped for a quick chat. Then, after one of the other police shouted something, he remembered what he was actually supposed to be doing and went to help his mates, who were rounding up the young gangsters. Amazing.

Digression over.

The internet is undoubtedly a fine thing, but here’s one was it has definitely made your life worse: you almost never have to talk to anyone you don’t want to any more.

In the era that might as well be christened Before Internet, your friends were basically whoever worked with you, or lived on your street. Now, although you probably know most of the people in your office, chances are you have no idea who your neighbours are. You don’t have to talk to cashiers or shop assistants or travel agents or bus drivers, since everything’s completely automated. You can happily get through a day only talking to your own friends, who you’ve pre-selected because they share your sense of humour and political opinions.

Doing that would be terrible. Not only is talking to people fun, it’s also fundamental to having a decent quality of life. Talking to people will help you make new friends, learn new skills, get favours done, get things fixed, get better treatment in shops and bars, learn about the world. It’s one of the most fundamental skills you can develop. Talking to people is often quite literally better than paying them when it comes to getting them to do things. Even if/when the world goes full-bore Day Of The Dead, being able to talk the gunstore owner into sharing his jerky with you is going to be more important than all that parkour you’ve been doing. Learning to talk to people is one of the never-discussed reasons why it’s a good idea to go to school, and yet hardly anyone deliberately tries to make themselves better at it.

I’m not amazing at talking to people, but I’m pretty solid. I decided to get better in my 20s, and I’m better than I was. There are lots of good resources out there for learning to do it: I recommend Dale Carnegie’s How To Make Friends And Influence People, which is deservedly popular, much less unpleasantly creepy than it sounds and actually more like a primer on why being a decent human being is a good idea. But really, there’s no substitute for actually doing it. You can practise on charity muggers – they’re desperate to talk to you. Or you can challenge yourself in everyday situations – I used to know a chap who regularly tried to make people who got into a lift with him laugh, and he only worked on the third floor. But you have to actually do it. You can work your way up to armed policemen, but you have to start somewhere.

HOMEWORK: This week, start a conversation with three people you wouldn’t normally talk to: someone in your office, someone at the gym, the person who gets you coffee – whoever. If you can make them laugh or otherwise brighten up their day, great – but just saying something non-necessary (including comments about the weather) and getting a response (anything that’s an actual word) counts. This might be easy, or it might be hard – either way, get it done. More next week.