Ever sent a text only to be met with a dry 'lol' or worse—a ghostly silence? Keeping a text conversation alive isn’t just about sending words. It’s about engagement that keeps the other person coming for more. Here’s how to master the art of texting and keep the conversation from flatlining.

When and why to keep conversations going

Before we get into “how,” let’s talk about why. Conversation is a dance – it should involve give, take, and reciprocity. There should be a point to the conversation, and the moment there is not, it is generally best to let it fizzle. Here are two simple principles you need to keep in mind before continuing a conversation:

Understand who you’re talking to

We’ve got to say it – many people are just not “texters.” They prefer in-person connections and do not want to carry on their day texting paragraphs about a show you both like. Try to figure this out early on in a friendship or relationship by taking cues from how the other person is texting you. Are they actively making conversation about things that don’t involve logistics (eg, making plans)? If so, it may make sense to engage with them more extensively in non-logistical conversation.

Generally speaking, most people fall somewhere in between texting solely for logistical purposes and being a deep conversational texter.

Understand why you’re talking to them

In every conversation, ask yourself, why did this conversation start? Did it start with a selfish request like, “Did you get the notes from yesterday’s class?” or “Did you remember to do X for me?” – they probably don’t want to chit-chat. If the conversation started more open like “How is it going?” or “Did you see the lineup for X music festival?” – it may invite more conversation.

How to keep text convos from going stale

Okay, now that we’ve identified further whether or not the recipient actually wants to chit-chat with you, let’s discuss how to keep conversations from running stale.

1. Always ask open-ended questions

Nothing kills a conversation faster than a yes/no question. Instead of asking, “Did you have a good weekend?” try, “What was the best part of your weekend?” This invites the other person to share more, giving you more to work with.

2. Use humor and playfulness

People love talking to those who make them laugh. If the conversation is feeling stale, drop in a witty comment, playful tease, or a funny meme that fits the mood. Example:

You: "I feel like today has lasted 47 hours. Please tell me something fun happened in your life."

Them: "I saw a dog in a sweater that looked like an old professor."

You: "Please tell me you got a picture. I need to see this wise old scholar."

3. Get descriptive in you responses

When you respond to questions, get descriptive and creative – this gives the other person more material to latch onto. For example, if they ask “How was your day?” Instead of just, “It was good – just went to work.” Instead say, “It was a weird. One customer told me he liked my feet.” Mentioning tiny details that made your day interesting, even if its weird, keeps conversation interesting and gives them a reason to tease or joke in their responses.

4. Bring up shared interests

Referencing past conversations or shared interests keeps things feeling personal. If they mention loving a certain TV show, ask if they’ve watched the latest episode. It shows you’re paying attention and keeps the convo flowing.

5. Leave Some Mystery

Instead of answering every question in full detail, leave a little room for curiosity.

Them: "How was your day?"

You: "Pretty wild, actually. I’ll tell you, but first—do you believe in manifestation? Cuz I think I might have done it."

Now, they have to ask what happened!

Casual Ways to Keep a Text Going:

React engagingly – If they mention a weird dream, say, "That’s wild. What do you think it means?" instead of moving on.
Make an observation – "You ever notice how Mondays feel like the longest day but also somehow go by fast?"
Drop a random but fun thought – "I just saw someone walking their cat on a leash. 10/10 confidence, zero fear."
Send a meme or TikTok – No words needed. Just vibes.
Playfully call them out – "You’ve been suspiciously quiet… plotting something?"
Throw in a lighthearted complaint – "I swear Uber Eats delivery people judge me based on my orders."
Make a ridiculous assumption – "I’m guessing you’re currently debating whether to make a snack or be productive."
Fake dramatic urgency – "Okay, important question: Is cereal a soup?"
Start a fake disagreement – "Unpopular opinion: Pancakes are just lazy waffles."

Notes from the experts

Always, always match their energy

If someone is responding with enthusiasm and long messages, match their energy. If they’re keeping it short and dry, don’t force a conversation—either take the hint or switch up your approach with a more interesting topic.

Don’t Be Afraid to End on a High Note

Sometimes, the best way to keep a conversation going is knowing when to pause. If things are starting to fizzle out, end the chat on a positive note, like: "I gotta run, but let’s continue this later—I need to hear more about that dog professor!" This leaves the door open for future texts.

Conclusion

Mastering text conversations is about reading the vibe, keeping things interesting, and making the other person want to keep engaging. Try these tips the next time you're texting, and you’ll never have to worry about the dreaded one-word reply again!

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