How to Have a Fun, Interesting Conversation Via Text

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.

EditSteps

EditHaving a Lively Conversation

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.
Ask for an opinion. People love it when you ask for their opinion 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.
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.
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 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! Don’t be afraid to be a little bit ridiculous; no one is judging you.
Talk about what you're doing. Another way to get an interesting conversation going is to talk about what’s going on with you. Even if you’re just watching television or getting ready to help your mom bake a pie, bring it up to see if it can spark an interesting conversation. This can also transition into having your friend talk about what he or she is doing. This is a way to feel closer to your friend and to feel more engaged in his or her life.
- Make sure you’re more interested in what your friend is doing than whatever is going on with you. Make your friend see that you really care about what’s going on with him or her.
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.
Send random, off-the-wall texts. There's something fun and playful about never knowing what a person will say next. Surprise him or her with a totally unexpected response, or a question that seems to come out of nowhere. Spontaneity is key, and it will make for another great string of conversation!
- Just like in a real conversation, you don’t want to overthink every word you have to say, or things will drag. Instead, if you suddenly want to bring up something funny that happened in class that day, or the topic of the weirdest documentary ever that you saw last night, go for it.
- Look around yourself for inspiration. The simplest, most common household item can spark a great conversation. It could be anything from a used napkin to a DVD.
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.
- Plus, nothing will slow down a conversation faster than having the person you’re texting ask you for clarification or having to repeat yourself.
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 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.
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 the 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…”
Send picture messages or messages with sound. These are extra fun! Send along a funny picture of yourself, or a cool graphic. 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.

EditFollowing Proper Etiquette

Make sure you really listen to what the person is telling you. 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.
- 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 your math class.
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.
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 may 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.
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.
Call the person up if you want to talk about something really serious. Though texting can be perfect for having a lighthearted conversation with one of your friends when you have nothing better going on, you want to avoid dropping a bomb on the person in the middle of what the person thought was a fun and interesting conversation. If you have some big news, or even some bad news, to share with the person, then you may be better off calling the person up or sharing your news in person.
- You want the person to be emotionally prepared for the gravity of the situation, not caught off guard.
- For example, you're causally chatting with your girlfriend about last night's television when she suddenly announces she's pregnant. Put yourself in their shoes: how would you feel if your friend dropped a bombshell on you through text?
Use the conversation to deepen your relationship in person. Remember that your texting relationship with a person can help you get closer, but it can never define your entire relationship. You should use texting to make conversation with the people you like and to get to know them again, but you shouldn’t let it replace human contact or real conversation. As much as you may like texting your new friend or love interest, you have to make an effort to call that person and to spend time with him or her in person if you really want your relationship to flourish.
- You can use texting as a jumping off point into having a real life connection with the person. For example, if you’re both talking about how your favorite movie is playing, you can ask a simple question like, “Want to go together?” Or if you’re both talking about how bored you are, you can say something like, “Want to go out for ice cream?” Don’t be shy about it; know that your friend probably wants to spend more in-person time with you, too.

EditFinding Interesting Topics to Text About

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:
- "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."
Follow up about something the person told you in person. One way to show the person that you really do care is to ask about something you talked about earlier that day, or even earlier that week. This shows the person that you really do pay attention and care about what happens when you're not just texting each other. Here are some ways you can follow up:
- "Hey, how is your grandmother doing? Is she still in the hospital?"
- "Did you get that waitressing job you applied for last week?"
- "How was your trip to Big Sur? I've always wanted to go."
Suggest something fun to do together. Another way to start a lively conversation is to suggest an activity that you and the person you're texting can do together. It can be something far in the future or later in the week; if the activity sounds fun, then you'll have plenty to talk about via text as you figure out the details. Here are some suggestions you can make:
- "What do you say to going to an 80s cover band concert with me next month? We can dress up in neon..."
- "Want to check out the new Wolverine movie this weekend? I heard popcorn is free this Sunday!"
- "Have you ever had Cambodian food? There's a new restaurant in town and I heard it's cheap and delicious."
Compliment the person. Compliments are never overrated, and you don't have to see the person face to face in order 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. As long as you're being genuine and not making the person feel uncomfortable, this is a great way to chat over the phone. 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."
Talk about fun plans you have for the weekend. Another way to have a lively conversation is to mention something fun that you're doing over the weekend or later in the week. This can be a great way to talk about something you're interested in, to share some funny information about yourself, or even to encourage the person to join in and spend some quality time with you. Here are some things you can say:
- "I'm going to a water park with my cousin this weekend. I always thought they were kind of corny, but I'm really excited."
- "I'm taking a ceramics class this weekend. Should be pretty cool."
- "I'm actually going to Tahoe with my family this weekend. I've never gone skiing before."
Encourage the person. 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 on 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."