Loneliness is awful – so every day I try to start a conversation with a stranger | Adrian Chiles


I enjoy having conversations like, you know, face-to-face, in person. Or just on the phone will do. Weird, I know. I’m assuming analogue chit-chat is dying out, as the rise of AI means we’ll have to get used to talking to computers. Already, many of the face-to-face conversations we are having were initiated via them. For example, I had a young male colleague, a good-looking and confident rascal. Even though, as far as I could see, he was enjoying conspicuous success with his Tinder dating, he bemoaned the march of technology. He said he’d often approach a woman in a bar, only to be told that she was waiting for a Tinder date. “The game’s over,” he said sadly. Tellingly, in relating this, it strikes me that approaching somebody unbidden to talk to them might now come across as dodgier than meeting a stranger you’ve found on the internet.

Whether you’re dating or not, the knack of starting conversations is at least as important – and challenging – as the art of conversation itself. The talking is the easy bit. It helps no end, of course, if you’re interested in other people, in which case you’ll generally bring yourself and others pleasure by asking them about themselves. If you’re more interested in yourself than anyone else, then that can be straightforward, too – just rattle on about your own brilliance and either turn a blind eye to any yawning or glazing over, or move on to your next victim. This is all set out nicely in Dale Carnegie’s famous/infamous book, How to Win Friends and Influence People. “Show interest in others” being his key point. I read it as a teenager and it made a huge impression on me – so much so that I gave it to a close friend of mine to read. His critique was exactly as follows: “This is all very well if you’re interested in other people, but I’m not really.” So that was that.

I wish Mr Carnegie had written another book called How to Start Conversations. I thought that I used to struggle with this but had got better at it. In fact, the opposite was true – if I’d ever had the knack, I had lost it. If you’ve been on the telly a lot, you tend to get recognised. Unaccountably, I suppose, this seems to motivate people to speak to you. It’s a great conversation-starter, but it’s always the other person doing the starting. This dawned on me a few years ago when Croatia’s Davis Cup tennis team beat Great Britain at Wimbledon. I was invited to the group’s celebration party at a pub in that part of London. The Croatian friend who’d invited me couldn’t come, so I knew not a soul there. But, no matter, I thought: I’ll just turn up and win friends and influence people with great enthusiasm.

In I walked, looking around in expectation of being engaged in conversation. Nothing happened. Nobody recognised me, therefore no one felt any urge to talk to me. OK, then I’d have to start a conversation. I opened my mouth to speak to someone, but nothing came out. I’d utterly forgotten how to do it. I really couldn’t think of what to say.

After half an hour shuffling about trying to look less mortified than I was, I resolved to leave. At that moment a physio who had worked in London for a time recognised me, said hello, introduced me to someone else, and it was all fine. But I’ve never forgotten that awful feeling of being lonely in a crowd. So, every day I try to start a conversation with a stranger, hoping they don’t edge away in alarm. And I hope I’m always as open as possible to a conversation anyone sees fit to start with me.

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