Tips to Keep Online Conversations Interesting

Source: Photographer: SHVETS production
Source: Photographer: SHVETS production

3 Strategies to Keep Online Conversations Interesting

Ever experienced this scenario? You’re texting someone new, and the conversation starts off great. But then, it fizzles out. The initial excitement fades, leaving you unsure of what to say next or how to maintain the other person’s interest. Such moments can be frustrating and uncomfortable for both parties involved.

So, how can you prevent this awkward situation? In this article, you’d learn three strategies to keep your online conversations interesting and fun. Whether you’re looking for friendship, romance, or something else, these tips will help you make a lasting impression. 

Strategy #1: Spark Curiosity with Open-Ended Questions

Open-ended questions are questions that invite the other person to share more details and opinions, rather than just giving a yes or no answer. These types of questions can spark curiosity, interest, and excitement in your chat partner.

You can use these questions whether you’re talking to someone you already know or someone you just met online. In fact, asking open-ended questions can be especially helpful when you are on platforms that help you match with random people online because it can help you break the ice and find common ground. Moreover, this valuable strategy is equally applicable during live video chats, ensuring engaging and dynamic interactions.

But how do you ask open-ended questions? Here are some tips:

  • Start with words like what, how, why, where, when, or who. These words encourage the other person to explain, describe, or tell a story. For example, instead of asking “Do you like movies?”, you can ask “What kind of movies do you like?” or “How do you choose which movies to watch?”
  • Avoid words like do, are, is, have, or can. These words usually lead to yes or no answers, which can end the conversation quickly. For example, instead of asking “Are you happy with your job?”, you can ask “What do you enjoy most about your job?” or “How did you get into your field of work?”
  • Follow up with more questions or comments. Show that you are listening and interested in what the other person is saying. You can ask for more details, examples, or opinions. For example, if they say they like traveling, you can ask “What’s the most memorable place you’ve visited?”

Strategy #2: Embrace the Power of Visuals

In online conversations, words alone may not always convey the full range of emotions or add that extra touch of personality. That’s where the power of visuals comes in. 

Humor, emojis, and GIFs are visual elements that can add some emotion, expression, and personality to your chats. They can also help you convey your tone, mood, and intention, which can sometimes be hard to do with just words. Here are some tips to use these visuals effectively: 

  • Use humor to lighten the mood, tease, or flirt. They include jokes, puns, sarcasm, irony, or exaggeration to make them laugh. For example, if they say they like pizza, you can say “Pizza is my soulmate. We have a deep connection.
  • Emojis are the digital equivalent of facial expressions and gestures. They can help convey emotions. Use emojis to express happiness 😄, laughter 😂, surprise 😮, or any other emotions that align with your conversation.
  • GIFs are short animated clips that can capture a specific mood or reaction. When a well-timed GIF is used, it can elicit laughter, convey excitement, or emphasize a point. Platforms like GIPHY or built-in GIF keyboards in messaging apps can help you find the perfect GIF for any situation.

Remember, visuals should complement your messages and not overpower them. Be mindful of the tone and context of the conversation when using humor, emojis, or GIFs

Strategy #3: Share Personal Stories and Experiences

Sharing personal stories and experiences is a powerful way to engage others and make your conversations more memorable. This can be a funny story, a quirky hobby, a passion project, or a recent achievement. Here’s how you can share something personal or interesting about yourself:

  • Choose something that is relevant, appropriate, and positive. You want to share something that is related to the topic of the conversation, suitable for the context. For example, if you’re talking about movies, you can share a story about how you met your favorite actor, or how you made a short film with your friends.
  • Use details, emotions, and senses to make the story vivid. For example, if you’re sharing a story about how you met your favorite actor, you can say, “I was walking down the street when I saw him coming out of a coffee shop. He was wearing a leather jacket and sunglasses.

Finally, always ask for their opinion, feedback, or advice on what you shared. However, avoid divulging sensitive information that could compromise your safety or the trust of others.


Mastering the art of keeping online conversations interesting is a game-changer. By incorporating visual elements, asking thought-provoking questions, and sharing personal stories, you can forge genuine connections and create engaging dialogues that leave a lasting impact.