How to Stop Having Dry Conversations

We Need to Talk

As per our last posts, we have stressed the importance of communicating and reaching out to friends and families during difficult times. The simple gesture of checking in on someone can make all the difference in their lives. But as many of us want to help, sometimes there arises the problem of how to help. While a quick conversation starter or funny gif may be enough for us to check in every now and then, the bulk of the conversation is what really matters. Yet, many of us fail to reach a real connection. I’m sure we’ve all been there: you’re talking to someone and, suddenly, the conversation stagnates and seems to die out without ever reaching anything meaningful. 

Listed below are ways we can avoid these kinds of awkward interactions and get to the bulk of what we mean to say. While this isn’t everything that makes an engaging conversation, these are what I’ve both heard and found to create more interesting discussions. 

It’s Not About You

When someone is sharing their own experience, don’t interject with your own or try to equate your experience. Few things are more inconsiderate than hearing someone talk about a difficult time and then interrupting to say how you are also struggling. No two experiences are ever the same, and you don’t really ever know the full story. It’s not a competition, and it’s not about you right now. While similar experiences are definitely comforting to the other person in letting them know they’re not alone, there’s a time and place for you to share. This is more of a disclaimer to not brush over or devalue their struggles. What they have to say is of the utmost importance, and it’s your job to make sure they know they are heard. 

Air on the Side of Caution

This is essential in any conversation: when you don’t know something, say you don’t know. There’s no need for pretending to be knowledgeable about something that you don’t know much about. Before you talk, take a second to think about the ramifications of what you are about to say. What kills a conversation usually isn’t what you don’t say, but what you do say. Our words have an enormous impact, one that we don’t fully comprehend. As conversations are a great medium to heal, we have to be cognizant of their potential to hurt others. 

Respond with More than a Reaction

This one is especially relevant over text; don’t respond with a simple reaction or blunt statement. I don’t mean to say the obvious, but there is no good response to “lol” or “that’s tough.”. So unless you want the conversation to die out, say something authentic or thought-provoking to keep it going. Open-ended questions are a great way to have an interesting conversation. Let them describe their experiences with more than a yes or no answer. Instead of asking, “Was it fun?” ask, “What was that like?” People tend to feel better when they get to relive their experiences by explaining them to others.

Be Transparent

This one should maybe be taken in moderation, but don’t be afraid to be open and share what’s on your mind instead of dancing around it. This one applies to several different situations. For example, when you want to express your appreciation for someone, I can understand the uncomfortableness of going out and saying it, but that vulnerability is how we can form stronger connections. Conversely, let’s say you’re in an argument that gets quite heated. Now, while transparency is essential in resolving conflict, there’s a specific way we can go about this. Rather than retaliating with verbal attacks of your own, try to calmly explain why you feel hurt by their words. This gives you and the other person a mutual understanding of how you interpreted the dispute. From here, you can work to a resolution that encompasses both sides’ feelings. Remember that your voice is meant to be heard, and sometimes it’s better to be blatantly honest than bottled up.

Keep an Open Mind and Be Interested in People

If you met David Dobrik or Beyonce (or any cool person for that matter), what would you say? You would probably want to ask the most engaging questions, the kind that would draw out the coolest answers. How come, though? Well, because they’re famous and have really original experiences. One thing we often fail to realize is that everyone has their own cool experiences. You need to appreciate that. Going into any conversation, you should acknowledge that the person who you’re speaking with has their own story that you don’t know. So be curious! Ask the thought-provoking questions that reveal the deep details, and genuinely care about what they have to say. Take it all as a new perspective, and hold back your judgments. With an open mind and by really caring about what someone says, you’ve got the right equipment to get some fantastic takeaways from any conversation. While your neighbor might not be a famous singer, there’s no doubt at all that they have something to share with you – just let them take the stage.


This is by far the most lacking skill I observe in conversation with others, and thus the most crucial to master. If there’s one thing to pick up from this article (although all are important), it’s got to be listening. A lot of people do what I refer to as “hearing”. It’s when the person in the conversation is taking in the words being spoken, quickly processing their literal meaning, and tossing back a response when prompted. True listening involves much more. It involves thought, emotion, and presence. You’ve probably heard that communication is only 7% verbal. This means that 7% of the information communicated in a conversation is shared through the literal words. 55% is through body language and the remaining 38% is through tone of voice. I don’t know about you, but my ears can’t read body language nearly as well as my eyes. When you’re listening, you need to be engaged. This engagement involves looking at the speaker and noting the nuances of the way they are talking. Not only will you understand the meaning of what they say much more thoroughly, but they’ll appreciate it too. Finally, when you’re truly listening you become much more capable of keeping the conversation going in an engaging way. The comments you make will be more suiting and the questions you ask will be more elaborate. Otherwise you’ll feel like you’re stuck in Vogue’s 70 questions series, just pummeling questions and answers back and forth until you’re tired

Ending Notes: Lost in Translation

What all of these tips have in common is that they essentially fall under the same premise: how to make sure what we want to say is not lost in translation. I truly believe that most people are well-intentioned in what they aim to communicate, but somehow fail to get that across. Whether it’s interrupting or not listening closely enough, these mistakes contradict what we seek out to do. It’s human nature to want to help and comfort others, yet it seems we can’t ever fully show that with our words. 

It’s our responsibility as people to try and express our compassion for another. As I preface again, these are only a handful of reminders to keep in mind during the midst of a conversation, but as you go about your busy day, try to actively implement at least one of these strategies the next time you interact with someone. These small adjustments make all the difference. 

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