What to Say to Keep a Conversation Going Over Text

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Expert advice for texting your crush, friends, or family
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Talking over text is a convenient way to get to know someone new or catch up with old friends, but sometimes it can be hard to figure out what to say next. Luckily, there are a ton of ways you can keep things interesting, like asking open-ended questions and discussing topics that interest you. We've got all the best tips and tricks you need to know to keep a text conversation going, including expert advice from dating coach Joshua Pompey.

Ways to Keep a Text Conversation Going

  • Ask open-ended questions so the other person can talk about their interests.
  • Send a funny joke, meme, or GIF if you don’t know what to say.
  • Try to give detailed responses rather than dry, one-word answers.
1

Ask open-ended questions.

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  1. Open-ended questions require more thoughtful, detailed responses than simple “yes” or “no” questions. If the other person just told you something about themselves, ask them to elaborate on that, or come up with your own open-ended question. This gives the other person an opportunity to talk about their interests in-depth. [1]
    • For example, “What would your dream vacation be?”
    • Or, “What do you like to do for fun?”
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2

Shift the focus to the other person.

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  1. To have a good conversation, both people should be asking and answering questions. If you feel like you’ve mainly been talking about yourself, redirect the conversation to the other person. Ask about anything: their favorite movie, their favorite restaurant, their job, their pets, etc. Let their answer be a jumping off point for the rest of the chat. [2]
    • For example, “Tell me about your new job. Are you liking it?”
    • Or, “Tell me more about your trip to Hawaii. I bet it was amazing.”
3

Avoid dry, short answers.

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  1. Remember, conversations are a two-way street, so make sure you put in the effort to respond to the person you’re texting. If someone asks you a question and you give them a one word answer, you’re forcing them to do all the work to keep the conversation flowing. Try to elaborate on your answer as much as possible and ask the other person questions in return so they don’t see you as a dry texter . [3]
    • For example, if they ask what your favorite food is, don’t just say “Pizza.” Instead, say something like, “Pizza. I know it’s pretty basic, but there’s this incredible spot downtown that comes up with really interesting toppings.”
    • Or, if they ask who your favorite music artist is, say something like “Taylor Swift. I got to see her in concert last summer and she was amazing. Who’s your favorite artist? Have you seen them in concert?”
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4

Ask about the other person’s day.

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  1. Asking about someone’s day is a pretty low-effort question that can actually lead to a lot of interesting conversations . Consider also telling them something about your day so you have something to talk about if they don’t have much to add. [4]
    • For example, “What did you do today? I went to the new bookstore after work and bought way more books than I should have.”
    • Or, “How was your day? You went to the lake, right?”
    • Make sure this doesn’t become your go-to question, however, as the other person could get bored. Pompey says, “When it comes to keeping conversations going, avoid the small talk and everyday questions, and just get into what's going on in your life or start out with a funny story or whatever it is.” [5]
5

Ask follow-up questions.

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  1. Instead of moving on with the conversation, ask follow-up questions about what the other person just said. This shows them that you’re paying attention to what they’re saying and making an effort to engage with them. [6]
    • For example, if the other person says they’re dreading going to work tomorrow, ask them “Why don’t you want to go? Do you not like your job?”
    • Or, if they told you they’re planning a trip to France, ask them which cities they’re visiting and what they plan to do there.
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6

Talk about your favorite topics.

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  1. In addition to getting to talk about something you enjoy, this allows you to see if you and the other person have something in common. If you both enjoy something, it will make it easier to keep the conversation going because you’ll both have a lot to say. If you don’t, the other person can ask you more questions to get to know you better. [7]
    • For example, “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.”
7

Send a meme or GIF.

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  1. If you feel stuck in the conversation but don’t want to end it just yet, try sending a related meme or GIF to lighten the mood and make the other person laugh. It’s generally best to choose something that’s at least somewhat relevant to the conversation, as sending a completely random meme could confuse the other person. [8]
    • For example, simply say something like “That reminds me of this meme…” and then send the image.
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8

Mention their social media posts.

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  1. 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. Only do this if you’re already friends on social media and choose a post that was recent so you don’t come across as intrusive or creepy. [9]
    • For example, “I saw your videos from the Chappell Roan concert. Was she good live?”
    • Or, “You posted that your sister is coming to visit, right? Are you excited?”
9

Tell them a joke.

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  1. If you can make the person you’re texting smile or laugh, they may be more willing to open up to you. Plus, you’ll be able to discover if you have the same sense of humor. 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. [10]
    • If possible, tie the jokes to what you were already talking about. For example, if you were talking about the ocean, try a joke like “What did the ocean say to the shore? Nothing, it just waved.”
    • Or, use a joke to start a new conversation. For example, “I just burned 2000 calories! That’s the last time I leave brownies in the oven while I take a nap.”
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10

Refer to a previous conversation.

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  1. If you’ve talked to the person you’re texting before, it can be easier to come up with conversation topics. Bring up something you thought of since your last discussion about something or ask a question about something they told you last time. This also shows the other person you care about your conversations and remember things they’ve told you. [11]
    • For example, “The last time we talked, you told me you were starting a new book. Have you finished it yet? How was it?”
    • Or, “Do you remember our conversation about penguins? I just learned a new fun fact!”
11

Play a game over text.

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  1. Games are structured, so playing one takes a lot of pressure off since you don’t have to worry about coming up with new conversation topics. Try suggesting a game like Truth or Dare , Would You Rather , or 20 Questions . These are all fun to play with friends, or they can lead to a flirty conversation with your crush. [12]
    • If you don’t want to play any of those, try sending each other riddles to solve or writing a story together by taking turns adding sentences.
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12

Ask for their opinion on something.

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  1. Most people are happy to share their opinions, so this can be a great way to save a dying conversation. Ask them about anything, like their favorite musician’s new album, an article you read, or a new restaurant that just opened up. Be sure to share your views, too, so they don’t feel like they’re being interrogated. [13]
    • For example, “Have you seen that new beauty trend that’s all over TikTok? What do you think? I’m not sure I get the hype.”
    • Or, “Have you heard Sabrina Carpenter’s new album? I think it’s her best work yet! Do you like her music?”
13

Switch topics if they seem bored.

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  1. Don’t be afraid to change the topic, especially if you’re talking to someone you’re just getting to know . Talking about a variety of things can help you figure out what you have in common, which in turn will often lead to longer conversations. [14] Pay attention to how the other person responds. If they seem bored or uninterested, try moving on to a different, but related, subject.
    • For example, if you love football but they don’t really enjoy it, try asking which sports they’re a fan of.
    • Or, if you’re a big movie buff but they prefer books, try talking about your favorite book-to-movie adaptation.
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14

Use some emojis.

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  1. Sometimes, conversations may die out because it’s hard to interpret the other person’s tone without hearing their voice or seeing their body language. While just sending emojis likely won’t save a conversation, adding them to your messages can help the other person feel more relaxed and open up more. [15]
    • For example, if you’re making a joke, add a laughing emoji so the other person knows you aren’t serious.
15

Send a photo or video.

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  1. 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 of a painting you just finished, send them a text along with it that says something like “I just finished this watercolor painting that I’ve been working on for 3 weeks. What do you think?”
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16

Ask if they need help with anything.

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  1. If the person you’re texting is venting about something that’s bothering them or talking about how stressed they are, offer to help them. Even if there’s nothing you can do, it may make them feel better and they’ll likely be more interested in continuing the conversation because you care. [16]
    • For example, if the other person is telling you about how they're fighting with their family, reply with something like "That's terrible, I'm sorry. Is there anything I can do to help?"
    • Or, if they’re getting ready to move, say something like, “Moving can be so stressful. If you want, I can come over tomorrow to help you pack.”
17

Prepare topics ahead of time.

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  1. If you know you struggle with coming up with things to talk about, making a list of topics could help you feel more comfortable. Think of things that remind you of the person you want to text, then write them down. That way, when the conversation starts to fizzle out, you can easily switch the subject.
    • For example, if the person you’re talking to loves Marvel movies, make note of any new trailers or movie news you can mention the next time you talk to them.
    • If you’re not sure how to change the topic, simply say something like “Oh, by the way,” and bring up the new topic.
    • Even if you have a pre-selected list of topics, Pompey says it’s important to make the conversation feel as natural as possible: “When you start conversations in a more natural way, it's A. more entertaining and B. it looks less desperate than just saying, “Hey, what's up?” because that makes it look like you're just sitting around, doing nothing but thinking of them.” [17]
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18

Avoid controversial topics.

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  1. Don’t push someone to talk about something they’re not interested in or may be uncomfortable discussing. If you bring up a topic they seem hesitant to talk about, move on to something else. Trying to force the conversation may cause the other person to withdraw and stop responding. [18]
    • For example, if you’re just getting to know someone, it’s usually best to avoid things like politics, religion, or sexual topics.
    • If you really want to bring up one of these topics, ask the person if they’re comfortable talking about it first. If they’re not, change the subject.
19

Avoid dominating the conversation.

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  1. If you’re excited about something, it can be easy to get caught up in what you’re saying and forget to ask the other person about themselves or their opinion. If this happens too often, the other person may lose interest in the conversation. Try to keep the conversation even and allow the other person to talk about themselves, too. [19]
    • For example, if the other person texts you that they had a bad day, avoid saying something like, “Me too. I missed the bus, and I was super late for work.” Instead, 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.”
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20

Respond quickly.

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  1. While you don’t need to respond immediately, not responding promptly could cause the conversation to fizzle out. 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. [20]
21

Don’t text them too many times in a row.

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  1. In general, try not to send more than two texts in a row while you’re waiting for the other person to text back. Texting someone repeatedly can be seen as a red flag, especially if you don’t know them well. Remember, just because it’s taking them a little while to respond doesn’t mean they’re ignoring you—they may just be busy! [21]
    • Pompey says, “Don't overdo it with the texting and don't blow up their phone to the point where they get sick of you. You want to keep that balance between somebody enjoying your text message and looking forward to them but not overdoing it.” [22]
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22

Call instead of text if you have something serious to discuss.

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  1. Some conversations are better held verbally than through text. If the topic is very important, consider calling to make the conversation more personal. This also allows the other person to hear your tone of voice so there are no misunderstandings. If your text conversation seems to be headed in this direction, simply ask if you can call them instead. [23]
    • For example, say “Can I call you? I think this would be better over the phone.”
    • Or, “Can we talk about this on the phone? Let me know when it’s a good time to call.”
23

End the conversation when it lulls.

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  1. Every conversation ends at some point, including the good ones. If you notice a natural lull in the conversation, it may be time to wrap it up. Keep things friendly and brief and let them know you’re ready to end the conversation. [24]
    • For example, say something like, “It’s been great chatting with you, but I’ve got to go now. Let’s talk again soon!”
    • Or, “I have to leave for my yoga class now. I’ll text you this weekend!”
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Texting Help

Expert Q&A

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  • Question
    What do you say to keep a conversation going?
    Joshua Pompey
    Dating Success Coach
    Joshua Pompey is a Relationship Expert and Founder of Next Evolution Matchmaking (NEM) based in New York City, NY. With over 15 years in the industry, Joshua helps his clients navigate online dating and has 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?”
    Thanks! We're glad this was helpful.
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    Not Helpful 8 Helpful 19
  • 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.
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  • 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.
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      • Don’t take things personally if the conversation doesn’t go as well as you’d hoped. You may have a better conversation next time. If not, it’s probably better to talk to people who are interested in talking to you, anyway.
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      References

      1. ↑ https://psychcentral.com/health/deep-conversation-starters
      2. ↑ https://www.eharmony.com/dating-advice/getting-to-know/how-to-keep-conversation-going/
      3. ↑ https://www.marriage.com/advice/relationship/how-to-not-be-a-dry-texter/
      4. ↑ https://bumble.com/en-us/the-buzz/how-to-keep-a-conversation-with-your-crush
      5. ↑ Joshua Pompey. Relationship Expert. Expert Interview. 27 November 2019.
      6. ↑ https://www.nbcnews.com/better/lifestyle/how-have-better-conversations-people-you-ve-just-met-according-ncna1005941
      7. ↑ http://www.businessinsider.com/how-to-keep-a-conversation-going-2011-1
      8. ↑ https://www.marriage.com/advice/relationship/how-to-not-be-a-dry-texter/
      9. ↑ https://www.forbes.com/sites/johnhall/2013/08/18/13-simple-ways-you-can-have-more-meaningful-conversations/#79a767fe4fe9
      1. ↑ http://ideas.ted.com/how-a-great-conversation-is-like-a-game-of-catch/
      2. ↑ https://www.marriage.com/advice/relationship/how-to-not-be-a-dry-texter/
      3. ↑ https://parade.com/1043064/marynliles/texting-games/
      4. ↑ https://bumble.com/en-us/the-buzz/how-to-keep-a-conversation-with-your-crush
      5. ↑ https://www.psychologytoday.com/us/articles/202305/the-art-and-science-of-great-conversations
      6. ↑ https://www.marriage.com/advice/relationship/how-to-not-be-a-dry-texter/
      7. ↑ https://www.ironcladfamily.com/blog/how-to-comfort-someone-over-text
      8. ↑ Joshua Pompey. Relationship Expert. Expert Interview. 27 November 2019.
      9. ↑ https://globalcareers.brandeis.edu/blog/2024/02/07/oops-small-talk-topics-to-avoid/
      10. ↑ http://ideas.ted.com/how-a-great-conversation-is-like-a-game-of-catch/
      11. ↑ https://www.marriage.com/advice/relationship/how-to-not-be-a-dry-texter/
      12. ↑ https://www.regain.us/advice/chat/how-often-should-you-text-a-girl-to-keep-her-interested-in-you-keeping-the-conversation-going/
      13. ↑ Joshua Pompey. Relationship Expert. Expert Interview. 27 November 2019.
      14. ↑ https://greatergood.berkeley.edu/article/item/should_you_call_or_text_science_weighs_in
      15. ↑ https://psychcentral.com/health/deep-conversation-starters

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