How You Can Hold Deep Conversations with Strangers

Meeting new people can always be nerve-wracking. Now imagine meeting new people and having to engage in surface-level awkward conversations, leaving at the end of the night with only the knowledge that they hate the cold and grew up in a town you’ve already forgotten the name of. And while there is nothing wrong with holding small talk to break the ice and start a conversation with a stranger, so often, we find ourselves stopping there. Rarely do we make it past that stage and move on to deep, insightful discussions that may even lead to the actual connection we all desire. 

Although some might think the solution to this problem is to try and escape small talk entirely, that might not be the best path to choose. You see, as boring as small talk can be, it can be the stepping stone you need to reach that connection. The key here is to use it to your advantage, ensuring that the ‘warm-up conversation’ you held has made the person you’re talking to feel more comfortable, allowing room for deeper discussion topics. Here are some tips on how to do just that.

Open Your Ears, Shut Your Mouth

Many don’t usually realize when engaging in any conversation that to push it to interesting levels and reach the potential of connection, one must actually keep quiet. When we start discussions with people we’ve just met or acquaintances we barely know, sometimes we get too in our heads, questioning what we should say next and whether or not it should be a joke. And as we overthink our words, increasing our anxiety and decreasing our confidence, we also fail to register what the other person is saying, missing information that can be used to further the talk and make it more interesting.

So instead of trying to cut them off and share a funny story to make them laugh, put in an effort to actively listen to what they are saying, taking in their words and thoughts. The more you do so, showing a genuine interest, the more they’ll feel comfortable opening up. Who knows, maybe that stranger in a dark dress could become a lifelong friend if you truly listened to her as she talked realizing that you have very similar opinions.

Ask Why More

What makes conversations great? While some credit that to the person they are talking to, that isn’t always the case. You could be standing in front of the most interesting person you’ve ever met and still manage to have a dull conversation, all because you didn’t ask the right questions. How can we expect questions such as “How are you?” or “What do you do?” to get us to deeper conversations with people when their answers typically require one or two words?

For that reason, ask why with honest curiosity and wonder. “Why do you do what you do?” “Why did you decide to leave your hometown and move here?” “Why was today a great day?” or “Why was it not such a good day?” By asking why you’ll slowly be able to learn more about the other person. This can be great in making conversations less surface level as you might find things you can relate to, consequently moving one step closer to connecting with what was once a stranger. 

Fight the Temptation to Not Be Vulnerable

So, you want to get the other person to warm up too and start sharing facts about themselves that are actually interesting… but how can you expect them to do so if you don’t share anything about yourself? Thus, next time when they ask about your day, instead of answering, “It was good,” tell them about that one embarrassing incident you had while picking up your morning coffee. Yes, some stories might be hit-and-miss. But some might also be all you need to find a connection to the stranger standing in front of you, possibly transforming them into more.

Don’t Be Overly Polite

Ask anyone what’s the thing they hate most about small talk and I bet their answer will be how one must be on their best behavior, not letting any of their personality shine through. Perhaps that’s why most small talk never turns into anything more. If you’re not giving the person you’re talking to a real glimpse of who you are, how can you expect the conversation to grow and become more interesting? For that reason, aim to bring some truth to your answers, even if they’re just about your opinion on a certain book. Instead of politely nodding along, share what you really think. If they agree, you will have found something you both relate to. If they don’t, you might spark a very stimulating debate that’ll definitely make you less of a stranger. 

Conclusion

One thing you might have noticed throughout the steps mentioned above is that they all serve one purpose. Whether you try to actively listen to more, share details about yourself or encourage them to share more, at the end of the day, these tips aim to help find things you and the mysterious stranger you encounter can relate to. That can be discovering an equal love for traveling, or even simply admitting that you both hate small talk. Finding some common ground, building a deeper conversation, and going beyond surface-level questions can certainly become easier.

Now, I’m not going to lie to you; the road to mastering how to move past small talk will surely be bumpy, and you won’t click with everyone you meet. But surely enough, after accumulating some embarrassing failed attempts, you’ll find it easier to turn these somewhat awkward first encounters into something more, meeting some really interesting people in the process. 

Photo: fizkes/Shutterstock

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