To preface this, I wouldn’t say I’m the most socially awkward person, but I definitely am more introverted. In conversations with more than just 2 people, with my close friends or with online chatting, I can easily keep a conversation flowing.

When it comes to 1 on 1 in person conversations with people I don’t really know, it gets awkward really quickly. I know asking questions is a great way to keep a conversation going but I also don’t want to sound like I’m just interviewing them.

I also feel like texting online gives you a little bit of a buffer to allow you to think of a better response but in person my brain just rushes to the first and probably not best response.

Any tips for me?

14 comments
  1. I love how this community has 3.7 million members, but no one cares to respond. Says a lot about the current state of the world

  2. Never found the answer to this, therefore I have no friends. I prefer to occupy my free time with projects or my kids eitherway. Though, my wife is the only person that has figured me out and the only one I have had consistent fun with.

  3. Well sometimes you just gotta let a conversation die.

    A conversation is a shared project between the two people speaking. You talk, I talk, you talk. I engage with you and you engage with me.

    If I am speaking with someone that doesn’t engage, doesn’t ask me questions back and doesn’t do their part in keeping the conversation alive and interesting, then I just disengage and let the conversation die.

    People’s ability and willingness to hold a conversation with you also tells you a great deal about whether they’re worth investing socially in. So I personally appreciate a pisspoor conversation, cause then I know not to talk to that person again.

  4. You need to have a nice mix of asking them questions and also offering information about yourself. If you feel like you are asking too many questions, spice it up and say “I really enjoy camping. My favorite camping spot…” Now, if they never ask you questions then I personally wouldn’t keep engaging with them in the future unless they start trying to get to know me because then it’s just one sided.

  5. Try this format:

    You ask a question.
    You listen.
    Then see if something catches your attention, that relates to you.
    You ask a clarifying question.
    Then once they clarify share something if they don’t ask you a question
    – oh that’s so interesting, it reminds me of this one time I..
    – yeah I know what you mean I have an uncle who…
    – I saw something like that on TV once, it really struck me that.

    At some point you want to share an insight or a storey and ultimately make connection from what they said to an experience, feeling or memory you have.

    There’s nothing wrong making the connection explicit, I mean I wouldn’t say ‘we connected 5 times tonight’ but that’s how conversation between friends and interested people work – you connect on common interests.

    I fucking hate sport. But lots of people like it. Sometimes I connect with other people just on the common interest of hating sport in general and then finding out if they have any exceptions to the rule, did they like any sport in school etc. sometimes the dislike of something shared is a connection too.

  6. Change the topic to something adjacent. Tell something about yourself that relates. Tell a story of something funny that happened. Talk about the weather.

  7. Pick one word from their story, repeat it and say: “tell me about it”. And if it dies, it dies. You can say you’re going to look for some snacks and leave.

  8. Storytelling and leading a conversation are both equally important skills that never get talked about as often as they should online. Id argue that these are more important than asking questions.

  9. First off, it’s ok to just start taking about what you’re interested in/ up to unprompted. A conversation starter doesn’t have to be a question. I’m like you, and I love questions. It would be great for people to ask questions so you feel more included, but that’s not a prerequisite for you including yourself. What did you do in between the time you last saw this person? Do you have a shared interest that you can bring up? These are the types of things you can just start talking about. You say a sentence or two then stop to let them reply. I think we like to imagine conversation as this perfectly flowing dialogue, but it’s not. It’s usually a couple awkward sentences until you stumble upon something you’re both really interested in and can talk about. That’s when the questions come easily.

    Now that being said, there are people that will talk on and on without giving you a chance to insert yourself or without asking you a question. Just stop talking if that happens. See what they decide to do. If they keep talking without you chiming in verbally, then they aren’t really talking to you, they are monologuing for their own benefit. You can choose if you want to stay in attendance or if you want to exit. But if they go silent after you’ve stopped talking. That’s great. Now you’re both silent. Let them think of something to say that will engage you.

    It’s also okay to confront the issue directly if it’s a friend that you value who falls into the latter case (talking too much without engaging you). I have told a friend that I feel like they’re not interested in my life because they vent a lot but they don’t ask me questions and so it’s hard for me to engage with them. Meanwhile, I’m the opposite, and I tend to ask too many questions. So sometimes I have to stop myself in conversation and sometimes theres a full minute of silence as I hear them rack their brain trying to figure out what to ask me about. But then they ask me something about my life. Theyre trying their best. It may seem like a very basic skill, but everyone has their own social strengths and weaknesses. I appreciate the people that listen to feedback and try to be better.

  10. Maybe you don’t have to actually force yourself too much to keep conversation going if there’s no more left to bring into table, might better if you just move on and leave as it is. But perhaps you can try to get to know about that person first before actually conversate with them and see if you can vibe with them greatly. Perhaps offering and tells a bit about your information might be better (only if they ask of course) and if they interested about it by asking more about it, that’s great but if they’re not, then move on is the only solution.

  11. It’s ok to be quiet.

    Then make statements

    Instead of saying “how was the movie” say “that movie must’ve been pretty good” they will then begin to talk about the movie

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