How to Keep a Text Conversation Going

Easy ways to keep someone engaged in your conversation

Co-authored by Joshua Pompey and Kyle Hall

Last Updated: August 23, 2022

Talking over text is a convenient way to get to know someone new and catch up with your old friends. If you're struggling to keep a conversation going with someone over text, there are some tricks you can use to keep things interesting and engaging, like asking open-ended questions and discussing topics that interest you. By sending meaningful texts and being a good communicator, you can start having long, enjoyable texting conversations with people.

Method 1

Method 1 of 3:

Asking Questions

1
Ask open-ended questions. Open-ended questions are questions that require responses other than “yes” or “no.” Text the other person an open-ended question and build the conversation off of their answer.
- For example, you could ask the other person “What would your dream vacation be?” or “What do you like to do for fun?”
2
Ask the other person to tell you about something. You could ask about anything; their favorite movie, their favorite restaurant, their job, their pets, etc. Don’t just let the conversation end after they give you an answer; let their answer be a jumping off point for the rest of your chat.^{[1]
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Expert Source

Joshua Pompey
Dating Coach
Expert Interview. 27 November 2019.}
- For example, you could text them something like “Tell me about your new job, are you liking it?” or “Tell me more about your trip to Hawaii, I bet it was amazing.”
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3
Ask questions when the other person shares things about themselves. Instead of moving on with the conversation, ask the other person to elaborate or ask them why they feel the way they do about something. Asking questions will show that you’re reading what the other person is saying and making an effort to engage with them.^{[2]
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- For example, if the other person says they’re dreading going to work tomorrow, you could ask them “Why don’t you want to go? Do you not like your job?”
4
Ask the other person if they need your help. If the person you’re texting is complaining about something that’s bothering them or talking about how stressed they are, offer to help them. The other person will be more interested in continuing the conversation if they feel like you care.^{[3]
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- For example, if the other person is telling you about how they're fighting with their family, you could reply something like "That's terrible, I'm sorry. Is there anything I can do to help?"

Method 2

Method 2 of 3:

Sending Interesting Texts

1
Text the other person about some of your favorite topics. Incorporating your favorite topics into the conversation will make it easier to keep the conversation going because you’ll have a lot to say about them. You can even make a mental list of topics you like so you never run out of things to say.^{[4]
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- For example, you could text them something like “I’m watching an old Alfred Hitchcock movie right now, I love classic horror films.” or “I can’t wait for the Super Bowl next weekend, football is my life.”
2
Send the other person a joke over text. Use the joke to lighten up the conversation and make the other person feel more comfortable texting with you. Just make sure you know your audience; don’t send a crude joke to someone you’re just getting to know (unless they’ve told you they like that sort of thing). Try to keep your jokes light and fun.^{[5]
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- If you can't think of a joke to send, text them a funny meme or GIF instead.
3
Talk to the other person about things they shared on social media. If they posted a funny article you liked on Facebook, mention it to them. If they shared a photo of their meal at a restaurant, ask them where they went to eat. Make sure the other person knows you’re friends on social media before you mention something they shared; you don’t want to come across as intrusive or creepy.^{[6]
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4
Text the other person a photo or video. Try to send something that’s recent and interesting. If you went on a hike recently and took some beautiful photos at the peak, send a couple of them to the other person. If you have a video of your dog doing something silly, send it to them. Use the photo or video as a way to branch off in the conversation. Make sure you provide some context so they understand what you’re sending them.
- For example, if you send them a photo a painting you just finished, send them a text along with it that says something like “I just finished this watercolor painting, I’ve been working on it for three weeks. What do you think?”

Method 3

Method 3 of 3:

Being a Good Communicator

1
Avoid dominating the conversation. Let the other person talk about themselves too. People like to talk about themselves, and you might push the other person to lose interest in the conversation if you keep turning the focus back on you.^{[7]
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- For example, if the other person texts you that they had a bad day, instead of replying “Me too. I missed the bus, and I was super late for work.” you could text back “I’m sorry, that’s the worst. Do you want to talk about it? If it makes you feel better I had a bad day too.”
2
Don’t push someone to talk about something they’re not interested in. If you bring up a topic over text and the other person doesn’t seem interested in discussing it, move on to something else. Trying to force the conversation to go in a certain direction may cause the other person to withdraw and stop responding.
3
Respond to the other person’s text in a reasonable amount of time. Not responding promptly could cause the conversation to fizzle out. You don’t need to reply immediately, but try to keep your response time under 15 minutes. If you’re caught up doing something and it takes you longer to respond, apologize and let the other person know so they don’t think you’re ignoring them.^{[8]
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Expert Source

Joshua Pompey
Dating Coach
Expert Interview. 27 November 2019.}

Texting Help

Text Conversation

Text Conversation between Acquaintances

Expert Q&A

Question

What do you say to keep a conversation going?

Joshua Pompey
Dating Success Coach
Joshua Pompey is a Relationship Expert with over 10 years of helping people navigate the online dating world. Joshua has run his own relationship consulting business since 2009 at a success rate of over 99%. His work has been featured in CNBC, Good Morning America, Wired, and Refinery29 and he has been referred to as the best online dater in the world.

Joshua Pompey

Dating Success Coach

Expert Answer

When it comes to keeping conversations going, you want to avoid the small talk and just get into the meat of the conversation. It could be a story, a question, or a joke, but skip the unimportant stuff. So let's say you’re gonna text someone, you might start the text with, “Wow, you won’t believe what my coworker just did”, or, “Have you seen this new Netflix documentary? I'm watching it right now, it's so crazy,” and then just let the conversation naturally evolve. When you start conversations in a more natural way, it's more entertaining and it looks less desperate than just saying, “Hey, what's up?”
Question

How do I keep a text conversation going if the other person doesn't ask questions back?

Community Answer

Tell them a little about your day, or share something in the hopes of getting a response.
Question

What if someone says "K" or "OK"?

Community Answer

This is generally just an acknowledgement they are listening, but it can mean they're getting bored, depending on the tone of the conversation.