How to strike a good conversation on a date in 2025

How to strike a good conversation on a date in 2025

Did you ever have an experience like this? You went on a date, you start to ask each other questions — what you do today, what do you like to do on weekends, where do you like to go on vacation…all the standard routine questions that helps you warm things up. At the beginning it’s like a reflex, you’ve answered a thousand times in your life and you have no problem to make yourself sound confident or ask ‘’what about you?’’. But then suddenly, the questions ran out and you were struggling to find something new to say, and the conversation just turned awkward, then probably silence.

Even if you are not a huge sports fan, hopefully you can imagine that all the best conversations are actually like “playing the game”. All the questions that help you slowly get into the zone are like warming up, like playing tennis, you started with serving each other politely. But to make a date ‘’fun’’ and really get to know this person, someone must step up the game, otherwise, the quality of the conversation will start to drop when you ask questions you don’t usually talk about because you never think of it. People love to watch sports games not just to see the flawless technique, but to see how those players also deploy tactics and strategies that deliver results.

Let me give you an example: During the date, you start to talk about your vacations. You thought ‘’Great! I just went on a vacation with my best friend to South America, I’ve got things to share now’’. You tried to think of some highlights to tell and share pictures on your phone, but you couldn’t think of the best details or find the exact picture to support your story…so then the story starts to become vague and no one is enjoying it. This scenario can happen on any other occasion, in a meeting, or when you are trying to meet people in a new event, etc.

But there are ways to improve this situation — to make your conversation more compelling. So now, you are the sports player, the South America trip is the ball you are about to serve, how you serve it is your technique, and how to let the other person listen, ask questions, have any emotional reaction is your tactic. The first thing you have to do is to recognize the ball and practice your technique before you serve it; that means before you tell anyone about this trip, write it down first. Were there any highlights in a trip? Any new discoveries? Anything new happened? What was fun? — Then you edit all those fun details into a good story, as a script. Read it to yourself and ask yourself if your words bring the vivid memory back to life? Would it be better if you structured the story in another way? And the tactic is the thinking process — you kind of put yourself in the other persons shoes and wonder how they will react to your story, and then think about how you are going to reply back. What if they don’t like it? What if they like it and ask me more questions? What kind off follow up question they might ask? — the more you think about it, the more you can anticipate, be prepared and play along.

This sounds like a long and huge process but can be done quickly in your mind once you are get good at it. After you put some of the balls in practice you will find it becomes a habit, a good one. The more balls you have, the more different techniques you develop, and the more tactics you can change. Try it next time, before you go on a new date, new events or when you know you will be meeting lots of new people and you want to strike a good conversation, leave a great impression. The only thing to remember is that don’t get too caught up by your own script and stop listening to what the other people have to say!

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