19 Tips to Have a Fun, Interesting Text Conversation

Make a text conversation more fun and less weird

Co-authored by Julia McCurley and Darlene Antonelli, MA

Last Updated: March 13, 2023 References

It can be a bit intimidating to have a fun or interesting conversation via text, especially if you’re trying to win over a new friend or have your eye on a potential significant other. The key to being a great texting conversationalist is not to overthink it and to be comfortable bringing up whatever’s on your mind. This wikiHow article shows you a few ways you can make your text conversation more interesting and fun.

Things You Should Know

The easiest way to ensure that your text conversation is fun and interesting is to compliment the other person.
Avoid boring or cliche conversations, like the weather.
If you want to show that you're actually listening to the conversation, refer to something they mentioned earlier.

1

Compliment them.

A compliment is a great way to break the ice. You can say something about what they wore or how much you enjoyed talking to them. Compliments are never overrated, and you don't have to see the person face to face to give a meaningful compliment. A small compliment can be a great way to start a conversation and to make the person feel like you really care.^{[1]
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Research source} As long as you're being genuine and not making the person feel uncomfortable, this is a great way to chat over the phone.^{[2]
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Expert Source

Julia McCurley
Certified Professional Matchmaker
Expert Interview. 30 September 2021.} Here are some great things you can say to compliment a person over text:
- "You were amazing in your basketball game yesterday. I was so impressed."
- "I loved the denim jacket you wore today. You're so awesome at wearing retro clothes."
- "Thanks for helping me study for the math test last night. You're such a good friend and I couldn't have aced it without you."
- Keep the compliment short and don't carry on with it for several texts because that's creepy.

2

Ask about their hobbies.

Start with a simple topic. You don’t have to reinvent the wheel here; just asking your friend if she’s seen the latest episode of your favorite show or what she did over the weekend is a great way to start a conversation. If you pick something that interests both of you, such as sports, TV, or the upcoming elections, then you’ll be off to a great start.
- Don’t put too much pressure on yourself to pick the best conversational topic ever, at first. If the one you start with is a no-go, then you can always find a way to change the topic. Remember that there’s a bit less pressure to maintain a seamless conversation than you’d feel over the phone or in person.
- If the person doesn’t bite or sounds busy, just switch to another topic that you’re sure will generate some more enthusiasm.
- Some example prompts are: "What is a popular thing that annoys you?", "What was something you liked as a kid?", "What's an unpopular thing that you like to do?"

3

Ask their opinion.

People love it when you ask for their opinion^{[3]
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Research source} and they are always happy to give it, whether you’re in person or texting. If you show that you really care about what the person thinks, then he or she will be happy to keep talking to you. Focus more on listening to what the other person has to say than giving an opinion of your own.
- Try to keep your questions open-ended. Instead of asking, “Did you like the new movie?” ask, “What did you think of the new movie?” or “Why didn’t you like the concert?” This gives the person more to work with.^{[4]
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- Some examples are: "What's a controversial opinion you have?" or "What do you think about pineapples on pizza?".

4

Give your texts personality.

Remind the other person that there's an actual human being behind the words on that little phone screen. Add smileys, emojis, and emoticons, or use text laughs, such as "lol", "rofl", "cqts", etc., if that suits your texting style. You want your friend to see your unique texting patterns, just as no one else could sound like you if you were to have a conversation in person.
- Don’t worry so much about telling your friend what he or she wants to hear; it’s much more important that you let the real you shine through than putting on some kind of a front.
- If you’re normally a bit goofy or silly, let this come through! You want your authentic self to show through your texts.

5

Avoid sending one-word texts.

It may be much easier on your thumbs than taking the time to type out a real message, but one word can seldom start a conversation. Whether you’re asking a one-word question or giving a one-word response, this can’t lead to a very stimulating conversation. The more words you use, the more you’ll have to work with in terms of having a fun and interesting conversation.
- If you do send a one-word text, follow it up with a longer explanation or more information. It’s okay if you like to talk in shorter sentences as long as you can keep the conversation going.
- If there’s really nothing more to say on the topic, you can follow up with a more open-ended question of your own or a comment about a new topic.
- Even if the person asked you a “yes” or “no” question, this doesn’t mean you should end it there; say “Yes and…” or “No, but…” and elaborate on your opinion or rationale. This will keep the conversation feeling more flexible and dynamic.

6

Make your texts legible.

While the occasional misspelling or abbreviation is cute and acceptable, it's not fun when a person strains their eyes trying to decipher your texts. Try to keep chatspeak to a minimum, especially if you’re talking to a person you haven’t texted too often before; give people a little while to get used to your texting style before you use anything too colloquial.^{[5]
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- Plus, nothing will slow down a conversation faster than having the person you’re texting ask you for clarification or having to repeat yourself.

7

Avoid boring, cliché, everyday conversations.

The usual small talk is helpful when you're absolutely desperate, but it seldom makes for memorable conversations. Instead of "Fine weather we're having", try to think of something more original. This is especially important if you’re trying to win over a new friend or a potential significant other; you don’t want to say what everyone else is saying.
- Avoid saying things that are too simple or basic, such as, “What’s up?” “I’ve had such a long day,” or “I’m tired today.” You’ve got to give the other person a bit more to work with if you want to stand out.

8

Reminisce.

If you're texting an old friend, you could always bring up the past to have a few laughs or to have a nostalgic moment. It's hard to go wrong with "Remember the time..." or "I miss when...". Just make sure your sentiment doesn't turn too nostalgic, or both of you may end up with that empty longing feeling and won’t be able to continue the conversation.
- Reminiscing like this may come off as random in the middle of a conversation, but if you want to kick off a conversation with an old friend you haven’t spoken to in a while, then sometimes the perfect thing to say can be, “Remember that time when…”

9

Send picture messages or messages with sound.

GIFs are extra fun! Send along a funny picture of yourself, or a cool graphic (like a GIF). Add audio of your favorite song, or weird sound effects, for added fun. Audio or picture messages are bound to get you both talking and laughing. This is a great way to wrap up a fun conversation, too. Leaving your friend with a lasting image will make that friend eager to pick up your next texting conversation.
- Just make sure you’re texting someone with a phone that is able to accept photos, sound effects, or other fancy additions. You don’t want to confuse your friend or make your friend feel left out by sending along a video or an image your friend can’t see.

10

Use emojis, emoticons, and more.

Your phone's keyboard will most likely can send emojis and GIFs. And as the saying goes, "A picture is worth a thousand words" – so why not use a GIF to display how your morning is going so far? The GIF will most likely make the other person you're texting laugh and more likely to respond.

11

Keep your texts upbeat and fun.

Even if you're bored, it doesn't mean that you have to let the other person know. If you constantly complain of boredom, then the other person may lose interest and stop texting, thinking they're boring you. Instead, focus on the positive things in your life and show some enthusiasm about whatever topic you’re discussing.
- Avoid using words repetitively. It's hard to have an interesting conversation when you get the same old, monotone replies every time: "Lol", "Ah", "Wow", "Oh", etc. Try to mix it up a little bit to let the other person know you take an interest in what they have to say. This will keep the conversation more fun than if you say the same old thing all the time.
- You can use some emoticons or exclamation marks to generate some enthusiasm, though you don’t have to overdo it, either.
- If you’re just having a bad day and aren’t up for being overly enthusiastic, let your friend know.

12

Refer to something they said earlier.

This shows that you've been listening to what they are saying and people love it when others actually listen to them. You may be too worried about what you’re going to say next or may be really excited to share your opinion about something to notice what the person you’re talking to is telling you. Maybe that person has a secret he’d really like to share, or maybe something is off and he’s clearly upset though he hasn’t said this explicitly. Pay attention to what the person is saying so you can respond appropriately.
- You don’t want to seem self-absorbed by ignoring signs that the person wants to talk or has something to share. If the person seems like he’s not telling you the full story, or if something really exciting happened to him, then give him his turn to speak.^{[6]
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- Carefully read over what the person wrote, especially if the message is really long, before responding. You don’t want to look like you’re only half listening when you ask a question about something the person just told you one minute ago.
- If the person is talking about something important and serious, then make sure you’re free to really engage with him. If your friend is telling you about her grandmother’s death, then you should call her and talk about it instead of half-answering her because you’re in math class.

13

Don’t overthink it.

One thing to keep in mind when you pick up your phone to start a texting exchange is that you shouldn’t put too much pressure on yourself. Don’t worry about saying the most perfect first line or telling the most hilarious story. If you obsess over this too much, then it will take way too long for you to actually contact the person you want to talk to, or to continue the conversation; the person may think you’re busy or losing interest when in fact, you’re obsessing over what you’re going to say next.
- It’s much better to keep the flow of an imperfect, natural conversation than to spend ten minutes crafting the most amazing story ever. Plus, you don’t always know what the person you’re texting is up to, and you may have missed your chance to talk to that person for hours.

14

Be patient.

If you just started a texting conversation, or even if you’re in the middle of a slow-moving conversation, you should consider that the person you’re talking to may be in the middle of something, or might be having a texting conversation with someone else, too. You don’t want to rush things or seem impatient by repeating your question, sending a ton of question marks after your initial comment, or being rude or snippy until the person gets back to you.
- Remember that the benefit of a texting convo is that you have a bit more time to craft a response. The downside is that the person you’re talking to may not be as engaged as he or she would be if you were talking in person; it’s best to accept that instead of putting the person off by acting impatient.

15

Keep the conversation balanced.

One thing you should keep in mind is that there should be a balance to the conversation. You don’t want the person to feel like you’re doing all the talking, or that you’re asking so many questions that he or she can hardly keep his or her answers straight. Just as in a real conversation, you should aim to do about half of the texting, and make sure to let the person share his or her ideas instead of being overwhelmed by yours.
- Remember that it’s more important to be interested than interesting. Instead of telling the person a million fascinating facts you learned that day, you’re much better off asking the person about his day, his ideas, or his experiences. People like talking about themselves more than you think.

16

Ask for advice.

People love it when you ask them for advice because it makes people feel good to think that they are knowledgeable about something and that they have wisdom to share. It doesn't have to be something really serious; just something you know the person would have an opinion about. Here are some questions you can ask:^{[7]
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- "I'm going to Santa Cruz for the first time this weekend. Any suggestions for places to eat?"
- "What do you think I should get my boyfriend for his birthday? I'm completely stumped."
- "Which dress do you think I should wear to the school dance? I can't decide."

17

Be encouraging.

If the person you're talking to has a big test, an interview, or just another important event going on, then you can send the person a text to show that you're thinking of him or her and that you wish him or her the best. A bit of encouragement can be just the thing the person needs to succeed and to feel like you really care. Here are some ways to wish the person some good luck:
- "Good luck with your test tomorrow. I know you'll rock it!"
- "Get some rest before your interview. You're going to wow them."
- "Kick some butt in the soccer game this afternoon! I'll be cheering in the stands."

18

Let them know that you've been thinking about them.

Much like people like to be complimented, they like to know that they've been in your thoughts. You can say something like:
- "I ate this hotdog and when I added more ketchup, I remembered your story about the ketchup bottle" or "This song came on the radio and it reminded me of you."
- It's nice to make people smile!

19

Play a game

If you've run out of things to say, you can play games to pass the time. Games like Would You Rather, and Guess the Song/Lyric/Movie Title encourage both text members to participate. You can also try flirty games, like 20 Questions or Truth or Dare.
- If none of those games appeal to you, try issuing challenges, like "Let's see who can tell the corniest dad joke" or "Guess what this string of emojis is saying."

Questions to ask Over Text

Fun Questions to ask Over Text

Community Q&A

Question

What if the person seems uninterested in texting you altogether and you seem to be the only person keeping the conversation going?

Community Answer

Have you considered the possibility that means he or she most probably doesn't like texting? If that is the case, then the fact they even text you is a good sign. On the other hand, if this person isn't keeping in touch with you in any way whatsoever, then they may just not be interested in connecting with you.
Question

How can I deal with people who don't text back immediately?

Community Answer

Patience, my friend. They may not be texting back immediately because they don't want to text, or because they're busy doing other things. Not everyone has at phone at hand all the time.
Question

What do I do if I can't think of interesting things to say to keep the chat lively?

Community Answer

See what that person likes. If they feel passionate about the subject you guys will talk for hours.