How to keep a conversation going (in person, by text and on video)

Most conversations do not die because people are boring. They die because both people are waiting for the other to say something. A few simple habits fix that. Here are nine that work in person, by text and on video, with examples you can borrow.

1. Ask open questions

Closed questions get one-word answers. Open questions invite a story.

• Instead of “Did you have a good weekend?”, try “What was the best part of your weekend?”
• Instead of “Do you like music?”, try “What have you been listening to lately?”
• Questions that start with what, how and why usually work best.

2. Follow up before you change topic

The most useful question is often the second one. If someone says they went hiking, do not jump to a new subject. Ask “Where did you go?” or “What got you into hiking?” One good follow-up is worth five new questions.

3. Share something back

A conversation is a swap, not an interview. After they answer, add a bit of your own: a similar experience, an opinion, a small story. It gives the other person something to ask you about, so you are not doing all the work.

4. Listen for “free information”

People mention extra details they are happy to talk about. “I am tired, I was up late finishing a painting” contains a painting. Ask about the painting. Picking up these threads shows you are really listening, and it never runs out.

5. Use the “and then?” trick

When someone is telling a story, short prompts keep it going: “No way, then what happened?”, “How did that go?”, “Were you nervous?” You do not need a clever question, just a sign that you want to hear more.

6. Have a few go-to topics ready

Keep three or four easy topics in your back pocket for silences:

• Recommendations: “Seen or read anything good lately?”
• Plans: “Anything you are looking forward to this month?”
• Light opinions: “Controversial question: is breakfast the best meal?”
• Something fun: a random question or a hypothetical.

7. Give answers with hooks

When you are asked something, do not stop at “good” or “not much”. Add one detail the other person can grab: “Pretty good, I finally tried cooking ramen from scratch. It was a disaster.” Now they have something to ask about.

8. Go a little deeper when it is going well

Once you are both relaxed, a slightly deeper question can turn small talk into a real conversation: “What made you choose that?”, “What is the best part of it for you?”, “If you could do it again, would you?” There are more ideas in deep questions to ask.

9. Match their energy

If they write long messages, write more. If they are short and slow, keep yours short too, or give them an easy question to answer. On video, smile, nod and react; people talk more when they can see you are enjoying it.

How to keep a conversation going over text

• Never end on a statement with nowhere to go. End messages with a question or a hook.
• Reply to the interesting part, not just the last line.
• Use a game when it stalls: this or that, would you rather or the 21 questions game.
• Do not double-text a wall of questions. One good question is better than five quick ones.

Continuing the conversation on a video chat

• Use what you can see, as long as it is not personal: a guitar on the wall, a cup of tea, a funny T-shirt.
• Talk about the shared interest that matched you, if there is one.
• Answer the conversation starter that appears at the start of the chat. Both of you see the same one.
• Keep personal details private. You can talk about your hobbies without saying your name, school, workplace or where you live.

When it is fine to let it end

Not every conversation is supposed to last. If you have tried a couple of open questions and the answers stay short, it is okay to wrap up kindly: “It was nice chatting, have a good day!” In a random chat, pressing Next is completely normal. There are more ideas in how to end a conversation politely.

Practise

Conversation is a skill, and practice makes it easier. A random text chat is a low-pressure place to try these tips: you have time to think before you reply, and every Next is a fresh start. When you feel ready, try video. For the very beginning of a chat, read how to start a conversation with a stranger.