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How to Have Deeper Conversations

Updated on
July 22, 2021
Lifestyle
How to Have Deeper Conversations

With COVID-19 vaccinations on the rise in the US and other parts of the world, reopening has begun, and people are socializing in person more and more. As we re-engage in some of the social activities that were dormant during the pandemic, we may find our conversational skills are rusty. 

While some people might lean into small talk as a way to get their feet wet, others might prefer to get into more meaningful discussions to process and share their experiences. However, substantive convos could take a certain level of comfort and practice.

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Consider these tips to help manage meatier territory.

Divide and conquer

If you’re finding that a larger group, or even a trio, is too much to handle, find a way to chat with just one person. People can feel more comfortable and are often freer with their words in a one-on-one setting. You may find that conversing with just one other individual not only takes the pressure off of social interactions but also can allow the chat to grow deeper. 

Keep things flowing

In tennis, each player must keep up with hitting the ball back and forth in order for the game to continue. Similarly, if you want to encourage a conversation to flow and move in a more substantive direction, each party must contribute thoughtful commentary. 

There are a few ways to support this. Instead of quick volleys, slow down the conversation and don’t be afraid to take pauses to consider your reply. If you tend to bounce from topic to topic, consider dwelling on one topic for a longer period of time by asking follow-up questions. To keep the chat engaging, you’ll need to listen and respond actively.

Be proactive

It can help to brainstorm deeper topics in advance. Consider mentioning your own interests or recent preoccupations. Perhaps you’ve recently taken a master class on cooking that surprised you with its depth, volunteered for a local organization, dabbled in the art of macrame, learned how to play a challenging board game, or went foraging with a friend who taught you which native plants not to pick for environmental and spiritual reasons. Anything that provokes curiosity and deeper inquiry from your partner is ripe for conversation.

Alternatively, you can think of some questions you have for your acquaintance. Ask what they’ve been learning lately, if they’ve taken up new hobbies or interests, etc.

Share observations

Sometimes it’s exhausting to ponder reading the news or a book after a long day of work, but staying current and aware will give you a leg up on having a variety of topics to discuss. You can stay current in whatever way you choose, whether it’s reading popular nonfiction books, listening to a true-crime podcast, or watching a live webcam of red-tailed hawks. 

When discussing media, literature, or current events, share your observations and opinions and ask probing “why” questions about the thematic issues behind the latest sensation to extend the conversation.

Keep it appropriate

Venting about work, family, or other concerns can feel like unburdening yourself, but those chats may be best saved for a close friend or therapist. Depending on the relationship you have with your conversation partner, going too deep could possibly make them feel uncomfortable. You can be open, vulnerable, and revealing without unloading. Disclosing something slightly personal, such as a hobby, a past experience, or a funny firsthand anecdote, can take your chat to the next step because it gives the other party permission to take the conversation beyond the casual and formal. You can also ask your conversation partner if they are in a place to hold space for you. 

>>Read More: How to Reconnect with Your Wider Social Circle

Ask follow-up questions

One way to unearth better, deeper conversations is by showing interest in what others say. Whether they want to share their thoughts depends on various factors, but you can give an opening by considering what genuinely interests you about the topic at hand and asking follow-up questions. These should be open-ended questions that inspire free-form answers. Often, these answers lead to stories. 

Conversely, close-ended (“yes,” “no,” or other single-word answer) questions can cause the conversation to dead-end before it reaches the deep end. For example, if someone shares that they visited Alaska last year, instead of asking “Did you like traveling there?” you can ask, “What are the strongest memories that you have from that trip?” Don’t hesitate to say, “Oh that’s really interesting” or “Please tell me more about that.” Similarly, you can share exploratory stories in response to their questions, invoking memories, senses, and connections to current or past events.

Find common ground

If the conversation veers toward something controversial or political, you might find that you and the other party have differences in opinion. In this case, it’s important to maintain empathy for their perspective, even if you disagree. On the other hand, finding common ground allows you to bond from a place of relatable experience. If you sense someone is turning away from a topic, strive toward commonalities. Explore potential topics like food, travel, sports, books, music, or general lifestyle. From there, you can spin the conversation deeper by showing interest in what the other party says.

Even if you’re finding that your conversational skills could use some sharpening, with some practice, it’s possible to have deeper talks with strangers, acquaintances, and friends. Establishing meaningful points of connection takes some effort, technique, and knowledge, but it’s not out of reach. Depth of understanding and sharing can also deliver sweet rewards, from stimulating your mind to forging fulfilling relationships.

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