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.
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.
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.
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.
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.
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.
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.
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!
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. 
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.
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.
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.
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.
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.
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.
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.
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.
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.
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: 
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:
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:
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:
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:
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:
Add New Question
What if the person seems uninterested in texting you altogether and you seem to be the only person keeping the conversation going?
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.
How can I deal with people who don't text back immediately?
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.
What do I do if I can't think of interesting things to say to keep the chat lively?
See what that person likes. If they feel passionate about the subject you guys will talk for hours.
What can I text someone that I have just met?
Get to know them! Ask them about what they like doing in their free time or about their hobbies and interests. If you want, you can start by saying something like, "Hey! Is this Becky? Just making sure I got the right number!"
How can I express my emotion if I haven't got emoticons?
You can use :) for a smile, :( for a frown, ;) for a wink and ;( for a cry. These are basic text usages that everyone can do using a keyboard and that everyone understands in the texting and email contexts. You can also use the exclamation mark and the question mark to enhance your statements, along with good quality emotive words from the English language.
What should I and my best friend talk about over text?
You could talk about interests. Or you could be random and ask, for example, "Should we swap phones?" Another thing you could talk about is the past (good things, or bad if you wanted) like "Do you remember that time when we...".
How can I get a girl to trust me?
Show that you are interested in her; listen when she talks about serious things; give her little compliments; and share personal things with her.
How can I think of topics to chat about?
Try to find a common interest, such as: a football match, latest film, studies etc. Start by asking a small question or making a small remark. Continue to express your opinions if the other person seems interested.
How do I know whether I am boring someone while texting?
Usually you will know if they are bored if their responses are becoming shorter (one word answers), they stop asking you questions/for your opinion, or if they take a long time to respond to you.
How do I find out if the person likes texting or not?
Ask them. You'll look flimsy if you try to make perceptive judgements about them and fail in the end. The only way to know for sure is if you hear what they have to say.
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Article Summary X
If you want to have a fun, interesting conversation via text, start by asking an open-ended question about a topic you think the other person is interested in, like their favorite show or a concert they went to. Keep your replies upbeat, and make them more interesting by adding exclamation points, emojis, and texting acronyms like LOL. If the other person mentions something they’re doing, ask them to tell you more about it. You can also send funny memes or pictures to keep the conversation going. Keep reading to learn how to turn your text conversation into an opportunity to hang out in person!
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Sep 15, 2016
"This helped me so much with my best friend, since she is moving away soon so I started texting her! Thank you so ..." more