When you can’t see someone in person, texting is a great way to stay in touch, but it can be difficult to keep the conversation going. If you’re not ready to say goodbye but feel like the conversation is stalling, try changing the subject or returning to something you’ve already discussed. Not sure where to begin? Don’t worry—we’ve compiled a list of different things you can text them to keep the conversation interesting and fun.
1 “What are you up to lately?”
With this tried-and-true classic, you can go old school. People don’t always get a chance to talk about themselves, which may seem obvious. Let the other person know you’re genuinely interested in what they’re going through, and they’ll be more likely to open up to you. You might learn that they’ve been working on an exciting new project, or they might share that they’re having difficulty—whatever they say, build on it by asking follow-up questions. If it does not lead anywhere, try something else.
Remember to ask open-ended questions that allow the other person to elaborate rather than questions that can only be answered “yes” or “no.” For example, it is preferable to ask, “What did you do today?” rather than, “Did you have a good day?”
2 “Tell me more about…”
You should follow up on something they said earlier. One effective way to restart a conversation is to return to something previously mentioned by the other person. You already know they’re interested in talking about it, so ask for more information. That demonstrates you’re a good listener, and when you’re interested in the person you’re speaking with, you appear more interesting as well.
Try asking a question like, “What did you decide on for dinner earlier? Was it worth it?”
You could also say, “I was going to ask, but you mentioned something about planning a trip for next weekend. What are your plans?”
3 “What are you watching these days?”
While getting some recommendations, liven up the conversation. If you’re at a loss for what to say next, look into what the other person is reading, watching, or listening to. If you’ve never heard of whatever they’re talking about, ask them to tell you more about it.
This is especially beneficial if they mention spending a lot of time at home watching TV, reading books, or listening to podcasts. Simply say something like, “I’ve been wanting to get into podcasts; where should I begin?” or “I’m looking for a new show to binge-watch; any recommendations?”
4 “What do you think about…?”
Begin the conversation by soliciting the other person’s opinion. Most people are eager to express their thoughts on various topics. Use this to your advantage by asking a question that allows your friend to tell you exactly what they think. Just keep it light—political and religious debates can get heated, and it’s easy to misinterpret tone over text. To be safe, choose something a little more lighthearted.
Attempt something like, “Okay, I need your professional opinion. Be truthful. What do you prefer: waffles, pancakes, or French toast? There is only one correct answer.”
5 “Today I found out…”
Take the initiative and talk about yourself for a few minutes. Don’t feel obligated to constantly press the other person to talk about themselves—too much of this will make them feel interrogated. Talk about something interesting you’ve done recently if you need a pivot. Hopefully, your chat partner will pick up the thread and ask you a few more questions!
For example, you could discuss something interesting you learned in school, tell a funny storey, or mention that you saw a rainbow for the third day in a row.
If you haven’t done much, try discussing something going on around you. Perhaps your younger sister is dying your dog purple, or perhaps you have new neighbours moving in.
You never know what will start a conversation, so don’t be afraid to say something out of the ordinary!
6 “You have the coolest…”
With a compliment, you can flatter the other person. You can never go wrong by complimenting the person you’re speaking with. If the conversation has come to a halt, try mentioning something you’ve always admired about them. Even a casual compliment may encourage them to open up a little more to you.
For example, you could express your admiration for them by saying something like, “When I’m down, you always make me feel better. “You’re the best!” or “I miss your incredible smile.””
You could also mention something you admire about them, such as, “I was going to ask you where you got that amazing jacket you were wearing the other day. That looked great on you!”
7 “You’re never going to guess…”
A cliffhanger will entice them. Sometimes a little encouragement is required to get someone really engaged in a conversation. Try pique their interest by leaving them guessing about what you’re going to say next. Just make sure your follow-up is strong so they aren’t disappointed!
If you have an interesting storey to tell, start 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 someone know you’re thinking of them. For example, if you’re eating at a restaurant you know they enjoy, you could say, “Guess where I am right now!” (You get extra points if you offer to bring them take-out.)
8 “When you were a kid, did you…?”
Inquire about the person’s childhood to learn more about them. If you’re texting someone you don’t know very well, but you’re pretty comfortable with each other, try asking questions about their childhood. This can reveal a lot about the person, from their family life to what is important to them now. Just keep in mind that childhood memories can be associated with a wide range of emotions, so refrain from probing if something appears to be a little sensitive.
Ask lighthearted questions like, “Who was your favourite Disney princess when you were a kid?” or “Did you have any awesome holiday traditions as a kid?”
9 “Remember that time…?”
Bring up an inside joke or a humorous storey. Bring up a funny memory between the two of you to make the other person smile. It could be a long-lost inside joke between you and your oldest friend, or it could be something silly said by the waiter the weekend before when you were on a date. Just make sure it’s something you both find amusing—if you’re laughing about something they thought was embarrassing, the other person may become irritated.
If you can’t think of anything, try sending the person a funny meme instead!
10 “I was just thinking…”
Simply say whatever random thought comes to mind. Don’t worry about whether it’s cool or smart—just say it. You might come up with something really interesting if you don’t censor yourself. As an added bonus, you’ll be able to determine whether the other person resonates with your own unique brand of weirdness.
“I was just wondering why people never evolved with purple hair,” for example, or “Have you ever noticed our math classroom always smells like mustard?”
11 “Are you free to video chat?”
Calling the person changes things up. If you don’t get everything you want from texting, see if the other person is willing to talk on the phone or chat on a face-to-face video call. You can pick up on a lot more nuance this way, and it’s a great option if you want to discuss something in greater depth than text can provide.
If the other person says they can’t talk because they’re too busy, you’ll realise why the text conversation was slowing down!
Wait a few moments before texting the person. When a text conversation slows down, it’s usually because the other person is busy or bored with texting. Or they could be thinking about something else. Instead of trying to fill every moment of silence, give the other person some space to decide whether they want to take the lead in the conversation or simply take a break for a few moments.
You don’t have to go full-on ghost, and don’t make it a waiting game by not texting the person back for exactly 17-and-a-half minutes. Simply find something else to do for a few minutes and see if the other person is still chatty.
13 “Talk to you later!”
If the conversation appears to be coming to an end, end it. If the person you’re texting sends you short responses or lags a lot between messages, they may be ready to stop texting. Rather than leaving things open-ended, bring them to a close with a friendly “Bye!” This will also make it easier to return a day or two later with a new conversation.
If your text conversations seem to go nowhere, it’s possible that you and the other person aren’t connecting. That’s perfectly fine—you don’t have to be interested in everyone. Concentrate your efforts on the people who want to talk to you!
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