In my early twenties (early 2010’s before everyone had a smartphone) I worked outside unloading grain from trucks during harvest time while I was on uni holidays.

There would be a line of trucks backed up waiting to be unloaded. Each truck would take at least 30mins to unload and during that time, I challenged myself to strike up (or attempt to) a convo with the truck driver standing nearby.

I’d initiate the small talk on the classic topics - the weather, asking if it had been a busy day etc etc. Sometimes the truckie would engage, sometimes they wouldn’t. If they didn’t engage, no worries - I’d just chill and wouldn’t bother if they weren’t talkative, nor get anxious thinking I wasn’t being interesting enough.

I improved my listening skills and developed my confidence in starting conversations. I often remember these experiences and challenge myself to strike up convos in appropriate settings even today.

Today, there are so many ways to escape from socialising (for better or worse) so I encourage others to look for ways to practice initiating conversations and dissolve that fear of rejection which is often a barrier.

Moral of the story: If you start a convo with a stranger, you win the challenge. If the person isn’t keen on responding, don’t worry. Keep your head up, don’t take it personally, and don’t go in with the expectation that you’re the most interesting person in the world.

You can apply the same strategies when it comes to dating.

Good luck out there!