Q&A for How to Keep a Text Conversation Going

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  • Question
    What do you say to keep a conversation going?
    Joshua Pompey
    Dating Success Coach
    Joshua Pompey is a Relationship Expert and Founder of Next Evolution Matchmaking (NEM) based in New York City, NY. With over 15 years in the industry, Joshua helps his clients navigate online dating and has a success rate of over 99%. His work has been featured in CNBC, Good Morning America, Wired, and Refinery29 and he has been referred to as the best online dater in the world.
    Dating Success Coach
    Expert Answer
    When it comes to keeping conversations going, you want to avoid the small talk and just get into the meat of the conversation. It could be a story, a question, or a joke, but skip the unimportant stuff. So let's say you’re gonna text someone, you might start the text with, “Wow, you won’t believe what my coworker just did”, or, “Have you seen this new Netflix documentary? I'm watching it right now, it's so crazy,” and then just let the conversation naturally evolve. When you start conversations in a more natural way, it's more entertaining and it looks less desperate than just saying, “Hey, what's up?”
  • Question
    How do I keep a text conversation going if the other person doesn't ask questions back?
    Community Answer
    Tell them a little about your day, or share something in the hopes of getting a response.
  • Question
    What if someone says "K" or "OK"?
    Community Answer
    This is generally just an acknowledgement they are listening, but it can mean they're getting bored, depending on the tone of the conversation.
  • Question
    What do girls like to talk about when chatting on text messages?
    Community Answer
    It depends on on the girl. Try asking about her interests and getting to know her better. Look for things the two of you have in common.
  • Question
    The person I chat with doesn't usually get back to me for a long timem and I run out of things to say. What can I do?
    Community Answer
    It may mean they just don't want to talk at the moment. If they don't respond in a hour, leave the conversation, as it's not worth just staring at your screen waiting for a reply.
  • Question
    What do I do if someone says 'IK'?
    Community Answer
    Just keep chatting, the abbreviation 'IK' means 'I know', just in case you didn't know.
  • Question
    It's hard to maintain a conversation with my boyfriend, because when I ask him open-ended questions, he replies briefly and without detail. How can I get him to talk more?
    Community Answer
    Try to talk to him about things that you know he's interested in - his favorite sports, books, shows, etc. But don't be afraid to talk about yourself too. If he likes you, he's probably interested in learning more about you. You might also just want to casually bring up the fact that you wish he'd be a little more communicative. A relationship is a two-way street and you shouldn't be the only one making an effort. If he absolutely refuses to make an effort, this is probably not the right relationship for you.
  • Question
    How do I understand someone that doesn't want to talk to me anymore?
    Community Answer
    If you're sure they don't want to talk to you anymore, you don't really have to understand them. Just accept that they have their reasons and move on. You won't get along perfectly with everyone in life, and it's important to learn that and not get upset about it.
  • Question
    How do I keep a text conversation going if someone ends a text with "Oh?"
    Community Answer
    You could continue carrying on with what you were saying. For example, "I started a new job today." "Oh?" "Yeah, the atmosphere is great, I love the people..." etc.
  • Question
    How do I re-initiate a dead texting conversation with a girl who gave no response?
    Community Answer
    If it's been less than a few days, just leave it be and give her time to get back with you. If it's been longer, you could shoot her something along the lines of "Hey, I saw (something she's into) today, and it made me think of you. How's it going?"
  • Question
    How do I make a person I like more open about life on text?
    Community Answer
    Find out their interests or something that is precious to them by using open-ended questions. Or you might talk about similiar interests or goals or whatever. Give them a reason to talk to you.
  • Question
    I chatted with a girl I met on an app and the conversation for that day ended on a good note.. But I'm not sure how to start a new chat with her. Please how do I do that.?
    Annabeth33chase55
    Community Answer
    Hi, (girls name)! I had fun texting with you yesterday. How are you doing? For the rest of the conversation, talk about you interests. Make sure to ask her questions too, though.
  • Question
    How do I get past the awkward talking stage in a conversation?
    Community Answer
    Simple: time. There will almost always be a point like that in a conversation, you simply have to work through it. Unfortunately, there is no trick to instantly get past it, because a conversation is a 2 way street. If you try to rush past it the the other person could become uncomfortable, and as terrible as that first step is, it's just not worth ruining the conversation to try to get past it before the other person is ready.
  • Question
    I already know some things about her, and don't want to be too pushy. What are some good questions to ask her?
    Community Answer
    Girls usually don’t find guys too pushy and like when guys ask questions of them because it can show that they’re interested in you. Depending on what she likes, you could, for instance, ask her when she practices a sport, when she has acting classes, etc. If she’s really into book, ask her for a recommendation. These were examples, you can really go around with your questions. The more creative you are, the better. The more attention you show her, the better. And remember to never be a dry texter.
  • Question
    How do I keep conversations alive when talking? How do I come up with interesting questions?
    Community Answer
    Try coming up with 5 questions that are broad but force them to give enough information to make another question off it: “What’s the best part of your job?”; “I enjoy the human interaction”; “Interesting, have you always enjoyed that sort of thing”.
  • Question
    What do I do if I keep making excuses when someone wants to hang out with me?
    Community Answer
    That means you don’t really want to hang out with that person for whatever reason, and that’s okay!
  • Question
    How do I be more playful when keeping a text conversation going?
    Community Answer
    When you get to know them better (or already know their interests), then maybe make a joke or send a meme to them about their interest(s).
  • Question
    If I ask a person "How is everything going?" and they reply with "Not so good", then how am I supposed to reply? I don't want to come off as too pushy.
    Community Answer
    You could answer something like "I'm sorry things are not going too well for you. Do you mind telling me what's wrong? I am here to listen and help you, but if you don't want to tell me that is okay too."
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