How to Save a Dying Conversation over Text

Co-authored by Julia McCurley and Amy Bobinger, BA

Last Updated: November 28, 2023 References

Texting is a great way to keep in touch when you can't hang out with someone in person, but it can sometimes be a little hard to keep the conversation going. If you're not ready to say goodbye but it feels like the chat is stalling out, you may be able to give things a boost by changing the subject or circling back around to something you've already talked about. Not sure where to start? Don't worry—there are a lot of different things you can try.

Here are 13 foolproof things you can text someone when it feels like the conversation is dying.

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1

"What are you up to lately?"

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Go old school with this tried and true classic. It might seem basic, but people don't always get much of a chance to talk about themselves. Let the other person know you're genuinely interested in what they have going on, and hopefully they'll feel comfortable opening up. You might find out that they've been working on a cool new project, or they might share that they're having a hard time—whatever they say, build on it by asking follow-up questions. If it doesn't lead anywhere, move on to something else. ^{[1]
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- Remember to ask open-ended questions the other person can elaborate on, rather than questions that can be answered "yes" or "no." For instance, it's better to ask, "What did you do today?" instead of, "Did you have a good day?"

2

"Tell me more about..."

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Follow up on something they said earlier. One great way to revive a conversation is to circle back to something the other person already mentioned. You already know they're interested in talking about it, so ask them for a little more detail. That will show you're a good listener —and when you're interested in the person you're talking to, you automatically seem more interesting too. ^{[2]
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- Try asking something like, "What did you end up choosing for dinner earlier? Was it any good?"
- You might also say, "I meant to ask, but you said something about planning a trip next weekend. Where are you heading?"

3

"What are you watching these days?"

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Liven up the conversation while getting some recommendations. If you're not sure what to talk about next, try digging into what the other person is reading, watching, or listening to. ^{[3]
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Expert Source

Julia McCurley
Certified Professional Matchmaker

Expert Interview. 30 September 2021.} If you've never heard of whatever they bring up, ask them to tell you a little more about it. ^{[4]
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- This is especially great if they mention they've been spending a lot of time at home watching TV, reading books, or listening to podcasts. Just say something like, "I've been wanting to get into podcasts, where should I start?" or "I need a new show to binge-watch, any suggestions?" ^{[5]
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  Julia McCurley
  Certified Professional Matchmaker
  
  Expert Interview. 30 September 2021.}

4

"What do you think about...?"

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Jump-start the conversation by asking the other person's opinion. Most people are more than happy to share their opinions about things. Use that to your advantage by posing a question that gives your pal the opportunity to tell you what they really think. Just avoid anything too serious—political and religious debates can get pretty heated, and it's easy to misinterpret tone over text. To be on the safe side, opt for something a little more lighthearted. ^{[6]
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- Try saying something like, "Okay, I need your serious opinion. Be honest. Waffles, pancakes, or French toast? There's only one right answer."

5

"Today I found out..."

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Take the lead by talking about yourself for a bit. Don't feel like you constantly have to push the other person to talk about themselves—too much of that and they might start to feel like they're being interrogated. If you need a pivot, talk about something interesting you've done recently. Hopefully, your chat partner will pick up the thread and ask you a couple of follow-up questions! ^{[7]
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- For example, you might talk about something cool you learned in school, tell a funny story , or mention that it's the third day in a row you saw a rainbow.
- If you haven't done much, try talking about something that's going on around you. Maybe your kid sister is dyeing your dog purple, or maybe you have new neighbors moving in, for instance.
- You never know what will spark a conversation, so don't be afraid to throw out something random!

6

"You have the coolest..."

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Flatter the other person with a compliment . ^{[8]
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Expert Source

Julia McCurley
Certified Professional Matchmaker

Expert Interview. 30 September 2021.} You can never go wrong by saying something nice about the person you're talking to. If the conversation has stalled, try dropping in something you've always liked about them. Even a casual compliment might encourage them to open up to you a little more. ^{[9]
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- For instance, you might share something you really appreciate about them by saying something like, "You always make me feel better when I'm down. You're the best!" or "I miss your amazing smile." ^{[10]
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- You might also mention something of theirs you really like, such as, "I meant to ask you where you got that awesome jacket you were wearing the other day. That looked so cool on you!"

7

"You're never going to guess..."

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Draw them in with a cliffhanger. Sometimes it takes a little encouragement to get someone really engaged in a conversation. Try amping up their interest by leaving them wondering what you're going to say next. Just make sure your follow-up is strong so they don't feel let down! ^{[11]
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- If you have a great story to share, open by saying something like, "The craziest thing happened at work today," or "You'll never guess who I saw!"
- This can also be a fun way to let the other person know you're thinking of them. If you're eating at a restaurant you know they love, for instance, you might say, "Guess where I am right now!" (Bonus points if you offer to bring them take-out.)

8

"When you were a kid, did you...?"

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Learn more about the person by asking about their childhood . If you're texting someone you don't know super-well, but you're pretty comfortable with each other, try asking questions to find out what they were like as a kid. This can tell you a lot about the person, from what their family life was like to what's important to them now. Just keep in mind that childhood memories can be tied to a lot of emotion, so try not to pry if something seems to be a little touchy. ^{[12]
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- Try asking lighthearted questions like, "Who was your favorite Disney princess growing up?" or "Did you have any awesome holiday traditions as a kid?"

9

"Remember that time...?"

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Bring up an inside joke or funny story. Get the other person smiling by bringing up a funny memory the two of you share. It could be a long-lost inside joke between you and your oldest friend, or it could be something silly the waiter said when you were on a date the weekend before. Just make sure it's something you both find funny—the other person might get annoyed if you're laughing about something they thought was embarrassing. ^{[13]
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- If you can't think of anything, try sharing a funny meme with the person, instead! ^{[14]
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10

"I was just thinking..."

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Just say whatever random thought pops into your mind. Don't worry if it's cool or smart—go ahead and blurt it out. If you don't censor yourself, you might just come up with something super interesting. And as a bonus, you'll get to find out whether the other person vibes with your own personal brand of weirdness. ^{[15]
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- For instance, you might say, "I was just wondering why people never evolved with purple hair," or "Have you ever noticed our math classroom always smells like mustard?"

11

"Are you free to video chat?"

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Switch things up by calling the person. If you feel like texting isn't quite giving you everything you want, see if the other person is up to talk on the phone or chat on a face-to-face video call . You can pick up on a lot more nuance that way, and it's a great option if you want to talk about something more in-depth than text can offer. ^{[16]
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- If the other person says they can't talk because they're busy, you'll understand more about why the text conversation was starting to slow down!

12

Nothing.

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Wait a while before you text the person anything. Sometimes when a text conversation slows down, it's because the other person is busy or bored of texting. Or, they might have something on their mind. Instead of trying to fill every moment of silence, give the other person some space so they can decide whether they want to take the lead in the conversation or just take a break for a bit. ^{[17]
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- You don't necessarily have to go full-on ghost, and don't turn it into a waiting game where you don't text the person back for exactly 17-and-a-half minutes. Just find something else to do for a little while and see if the other person is still feeling chatty.

13

"Talk to you later!"

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Let the conversation go if it seems like it's over. If the person you're texting is sending you short responses or lagging a lot between messages, they might be ready to take a break from texting. Instead of leaving things open-ended, give things a clear end with a friendly "Bye!" This will also make it easier to pop back in with a fresh conversation a day or two later. ^{[18]
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- If your text conversations usually seem like they don't go anywhere, you and the other person might just not be connecting. That's totally fine—not everyone has to be interested in you. Focus your energy on the people who do want to spend time talking to you! ^{[19]
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Questions to Restart a Conversation

Join the Discussion...

What are some good deep convo starters to ask?

13

WikiToadDiver848

Any good deep conversation starters to get to know people better/tips for keeping a conversation going? Drop em here please and thank you... Read More

Lisa Shield
Dating Coach

What I recommend to help you have incredible and deep conversations is not to just skip from subject to subject. Very often conversations turn in... Read More

WikiCaribouTamer938

I think to have a deep conversation, you need to first be genuinely interested in the other person and what they have to say. If you're more focu... Read More

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Question

How do you keep a conversation going with your crush over text?

Julia McCurley
Certified Professional Matchmaker
Julia McCurley is a Certified Professional Matchmaker, Relationship Coach, and the CEO of Something More, Austin's premier matchmaking service. She has been creating happy couples in Austin for over 12 years and has helped hundreds of singles on their journey to finding love. Her blogs have been published on the Huffington Post, Good Men Project, SheKnows, Emlovz, and The Dating Truth. She also just published her first book, Game Set Match: A Professional Matchmaker's Advice on How to Win At the Game Of Love. Julia holds a BA in Business and Communications from The University of Puget Sound and received her Master Executive Matchmaker Certification from The Matchmaking Institute.

Julia McCurley

Certified Professional Matchmaker

Expert Answer

If you run out of subjects to discuss, text something that you have in common with them, like a show you both like. For example, write something like, “Have you seen the latest episode of that TV show?"

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Question

How do you fix a dry text conversation?

Julia McCurley
Certified Professional Matchmaker
Julia McCurley is a Certified Professional Matchmaker, Relationship Coach, and the CEO of Something More, Austin's premier matchmaking service. She has been creating happy couples in Austin for over 12 years and has helped hundreds of singles on their journey to finding love. Her blogs have been published on the Huffington Post, Good Men Project, SheKnows, Emlovz, and The Dating Truth. She also just published her first book, Game Set Match: A Professional Matchmaker's Advice on How to Win At the Game Of Love. Julia holds a BA in Business and Communications from The University of Puget Sound and received her Master Executive Matchmaker Certification from The Matchmaking Institute.

Julia McCurley

Certified Professional Matchmaker

Expert Answer

Say something flirty and slightly suggestive, like saying you just got out of the shower and were thinking about him. Complimenting him is also a good way to renew the sparks!

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Try writing down a couple of conversation ideas ahead of time. That way, if the conversation starts to fizzle out, you'll have something else you can quickly switch to. ^{[20]
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How to Save a Dying Conversation over Text

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wikiHow Texting Coach - Write the Perfect Text

"What are you up to lately?"

"Tell me more about..."

"What are you watching these days?"

"What do you think about...?"

"Today I found out..."

"You have the coolest..."

"You're never going to guess..."

"When you were a kid, did you...?"

"Remember that time...?"

"I was just thinking..."

"Are you free to video chat?"

Nothing.

"Talk to you later!"

Questions to Restart a Conversation

Join the Discussion...

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