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. Don’t put too much pressure on yourself to pick the best conversational topic ever, at first.
If the person doesn’t bite or sounds busy, just switch to another topic that you’re sure will generate some more enthusiasm.
If you’re just having a bad day and aren’t up for being overly enthusiastic, let your friend know.
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.
Make sure you’re more interested in what your friend is doing than whatever is going on with you.
If you do send a one word text, follow it up with a longer explanation or more information. 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. Just like in a real conversation, you don’t want to overthink every word you have to say, or things will drag.
Plus, nothing will slow down a conversation faster than having the person you’re texting ask you for clarification or having to repeat yourself. Just make sure you’re texting someone with a phone that is able to accept photos, sound effects, or other fancy additions.
If the person is talking about something important and serious, then make sure you’re free to really engage with him.
It’s much better to keep the flow of an imperfect, natural conversation than to spend ten minutes crafting the most amazing story ever. You can use texting as a jumping off point into having a real life connection with the person. 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.
We've all been faced with a seemingly-impossible task: keep a conversation with a girlfriend going when it seems there is nothing of worth to discuss. Relate back to earlier topics in the phone conversation to prove she has maintained your interest. Silence for more than a few minutes in a conversation could be avoided by asking some questions. If you know the person, review a mental list of topics you’ve discussed previously and continue on one of them. If you just don't like talking on the phone, let your girlfriend know that and maybe you could talk on the computer through IM. The key to being a great texting conversationalist is not to overthink it and to be comfortable bringing up whatever’s on your mind.
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. It's hard to have an interesting conversation when you get the same old, monotone replies every time: "Lol", "Ah", "Wow", "Oh", etc.
Another way to get an interesting conversation going is to talk about what’s going on with you. 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.


It’s okay if you like to talk in shorter sentences as long as you can keep the conversation going. 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. 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. The usual small talk is helpful when you're absolutely desperate, but it seldom makes for memorable conversations. 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. 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.
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. 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. 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. 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. 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. Remember that your texting relationship with a person can help you get closer, but it can never define your entire relationship.
Another way to start a lively conversation is to suggest an activity that you and the person you're texting can do together. Another way to have a lively conversation is to mention something fun that you're doing over the weekend or later in the week.
However, don't fret: it's simple, don't worry--and with some time and a cautious mouth, you will be able to converse easily and smoothly with your girlfriend. Just show interest in her having to rest in what she is about to be busy doing and then with a joke insist she has to find her way to work or something. Even if you have to give an opposing opinion, don't be too forceful with a disagreement though.
It's easier to start interesting conversations when you invest in developing your own interests. A talking point is something you can use to initiate an interesting conversation with someone. 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. Remember that there’s a bit less pressure to maintain a seamless conversation than you’d feel over the phone or in person.
Add smileys and emoticons, or use text laughs, such as "lol", "rofl", "cqts", etc, if that suits your texting style.
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. Whether you’re asking a one-word question or giving a one-word response, this can’t lead to a very stimulating conversation.
Surprise him or her with a totally unexpected response, or a question that seems to come out of nowhere.


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.
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.
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 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.
A small compliment can be a great way to start a conversation and to make the person feel like you really care. 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. Don't try to be too cool; she likes someone who sincerely cares, and you should if she's your girlfriend. Another good way to respond to a question you like is to share your interest in that topic. Focus more on listening to what the other person has to say than giving an opinion of your own. Instead, focus on the positive things in your life and show some enthusiasm about whatever topic you’re discussing.
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. The more words you use, the more you’ll have to work with in terms of having a fun and interesting conversation. 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.
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. 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. 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. Broaden and deepen your interests by having the attitude that you are interested in everything. Saying, "Oh - I like that question," can help others get to know you, making it easier for them to converse with you. Another way to broaden and deepen your interests is to ask questions about others' interests.
If your friend loves baseball, ask him which teams and players look good this year or ask him questions that clarify the league structure.
Leaving your friend with a lasting image will make that friend eager to pick up your next texting conversation.



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