How to NOT have “Empty” Conversations (Pt 1 of 2)
We have all found ourselves in a spot of having nothing to talk about with someone we barely know. After all, we just met and don’t truly know much about each other!

Hence, I know the problems we’d face when we find ourselves in such spot and I’ve compiled a list of topics to talk about or more specifically, questions to ask a person, in order to get to know them better and avoid stepping into the trap of awkward silence.

These questions can either be used with someone whom you’ve just met off the street and are trying to get to know, or even with your pals whom you’ve known since your days of running around in diapers. Best thing about these questions?

Like all other questions, it can go both ways but its way more interesting to talk about as compared to the typical “Speed Dating” questions like “What do you do for work?” or “How old are you?” and etc. You know what I mean.

These questions are much MUCH more meaningful and significant than “Do you like to eat pizza?” Once you’ve asked, the askee may even ask you back and thus, start an interaction where you guys start bonding! Let the magic of human interaction begin 😉

Below are 9 awesome questions to ask. I have another 9 more lined up but I figured putting them together is too overwhelming so I decided to separate them.

Find Part 2 here!

 9 of 18 “Awkward-Silence” Killer Questions:

  1. “What is something you have tried, but will never do again?”
    Woah, ain’t this a memory digger? Bet you just started digging a little too 😉

    This is an intriguing question that will get ANYONE thinking. Aside from being a good past experience digger, it also allows you to gauge how wild or daring your new friend really is. Perhaps the both of you have had the same experience and this will bring you closer together.

    If it’s something REALLY personal and your new friend actually discloses it to you? Congrats bud, you just earned his/her trust. Do not betray their trust by sharing it with other people or you’d end up losing it and causing a lot of problems for everyone. They disclosed something personal to you for a reason.Cherish their trust.

  2. “When you die, what would you want people to remember you for?”
    Another question that sends the brain’s neurons scatting off and pulling its drawers for memory files. Some people are ambitious and some aren’t.

    We all have our reasons to do what we all do but the question which we all tend to forget: What am I doing all of this for? So far, I’ve only met people with two types of answers.

    Either with a Goal/Ambition, or without. People who has no goals nor ambitions in life tend to answer “I don’t know” and when that happens, you can try suggesting that they maybe they’ve wanted to do something in the past when they were a kid (Become an Astronaut?) and they can consider to start working towards it!
    But, there’s a reason why they aren’t ambitious so, if they don’t respond well to that suggestion, you can try helping them to see that maybe it’s not impossible (Usually things are only impossible if you limit your mind to believe that it is) but if they still choose to be negative about themselves, it’s fine. Don’t push any further.
    Though they may not be ambitious, it doesn’t mean they aren’t good people! So if you happen to meet someone like this, do not judge them too quickly and start ignoring them.

    If you meet one who knows what he/she wants? They’d not only answer your question, they might even start telling you their plan on how to make it a reality! Who knows, you guys might even have the same goal/idea and end up working together. Awesome!


  3. “If you are given the resources and hired to write ANY Book/Movie script you want, what would you write about? Why?”
    This question speaks more towards the personality and sometimes, one’s preference of entertainment. People who wants to write about Fantasy genre would tend to be those who are very imaginative in their mind and may find themselves wondering on how nice it’d be if they can just get sucked into the Fantasy world itself.

    Most people I’ve met of this genre tend to be more carefree and needless to say, LOVE the idea of the alternate universes that’s been created by the many geniuses of the genre and they definitely enjoy watching, reading and listening to media of that genre.

    An example:
    Personally, I’d write a book about self-help because I’ve been through some horrible social experience in the past and I definitely don’t want others to experience what I did so if I can do something about it, I will and writing a book actually does help!Did you learn something about me through that answer? I’m sure you did. Regardless on whether you know me personally or not.

  4. “Who is your best friend?”
    Best friends must like you if the relationship were to ever have a chance of sustaining and working out. After all, we can cut ties with anyone at anytime. Why is this specific person/people still hanging around you? Why do you guys still choose to hang out together?

    By knowing who their best friend is, you will be able to judge whether you truly want them as a friend, then make a good first impression and will be able to ask more questions about them.Follow up questions to ask:
    “What are they like?”
    “How did you guys meet?”Objective

    here is to find out whether you guys are compatible and would help bring value to each other’s lives. If not, DO NOT waste both of your time trying to impress and befriend. There is not a reason to.46fe69eb999fa6ca7368f75a5baadabfde058580c1a1a3cffbdccffdf0e76cd6

  5. “What is one thing you wish you could undo from your past?”
    We are all humans. We make mistakes. Some of these mistakes are very difficult to understand and admit. If someone actually decides to share one of this with you, it will bring the two of you closer together for sure. Bonding is just so beautiful 🙂
  6. “What is your biggest fear?”
    Fear can be used as a weapon against you. If you actually reveal such vulnerability to someone, it shows how much trust you have placed in them. Hence, someone shares this with you? Respect and thank them for it.

    Fear can be seen as something negative but guess what, they allow you to really get to know a person. Knowing one’s biggest fear means you can further protect and know them better emotionally. Neat huh?

    But please, be considerate with the pranks (I know how mischievous some of you are. Myself included) and do not go overboard with it when April 1st hits.

  7. “Would you rather have love or money?” **Dates**
    This one is more for when you are going out with a Date. We all know where this is going so I won’t elaborate further. BUT, if they say: “Money, so that I can let my friends and family have a comfortable life and donate some to charity to help some needy folks too.”

    And he or she is truly sincere about it and you start avoiding them?

    I don’t know who you are. I don’t know what you want, nor where you live but I will find out. Fly over, track you down and slap you in the back of your head.Bad you.

  8. “What is your favorite childhood memory?”
    A trip down the good side of Memory Lane is always a great way to make someone feel safe and happy as they reminisce and invite you to walk hand in hand beside them through their experience, letting you learn more about them “First-hand”.

    Everyone has a childhood memory that really makes them smile and happy.By getting to know their memory, you will be able to know exactly which part of their life was the most special and maybe you can do something special for them in future when the need arises.

    Aren’t you sweet 😉

  9. “What is your most embarrassing moment that you can remember?”
    Embarrassing moments are times we can look back on and laugh. This is a good question because it will make both of you laugh.

    I remember one time when I actually tried to scare a monkey by running after it but it ended up with me running away from it because it started chasing me!dc10efa2a63c2ca4084f18455d579cd83c4ee39d73708b21b22bd99bfff2afd2


So, I shared the (18) questions in the past with a fellow blogger, who tested and tried them and that led to some insights so I’m adding it here because I feel that it’s beneficial for you to read. I got her permission to add her feedbacks into the post too, in case you’re wondering 😉

Ruth (From Ruth E Hendricks Photography):
“Your post came at a perfect time as this evening I attended a party with a large group of people I’d never met.

Instead of asking, What do you do? I discovered that the man I was speaking with has gone white water rafting and would never go again and that he is truly afraid of clowns. I was telling him about your blog post and how to avoid empty conversations and I asked him if I could test out a few of the questions. He was game. It was interesting and fun.

What I noticed is, he didn’t ask me anything at all so I thanked him and thought I had just better do it in a more natural way. It was just so wild that on the very day your post was up, I was invited to a surprise birthday party. Thank you.”

My Respond:
“Hahaha glad it helped!

I actually forgot to mention that it’s also perfectly normal that people don’t ask the question back because sometimes, we all get too caught up in the moment of wanting to express ourselves to the other party and we forget to ask about them in return.

Especially when the other party is so willing to get to know you!
Thanks for pointing this out to me. This brings me to something else which I’d like to point out, that can help in smoothening the flow of the conversation.

If your new friend actually started talking about something which you have a little bit of experience yourself? Share it!

It might create a separate special bond which only the two of you would have in the crowd cause you guys share something in common which says familiarity. It’s what we humans tend to look for! It’s also what separates you from the others and make you stand out 😉
I would like to add both your comment, along with this comment of mine to the post if you don’t mind, Ruth? I feel that it will be beneficial for everyone so let me know! Thanks for reading and actually applying it too haha!

Awesome to hear stories like that and I am happy to hear that you had a good time chatting up with someone new too 😉

Author’s note:
Find Part 2 here!
Want more epic goodness by me?
Check out this fun video I’ve made in my previous blog post

11 thoughts on “How to NOT have “Empty” Conversations (Pt 1 of 2)

  1. This is great! I actually went out the other night, for the first time in awhile, and had a blast playing truth or dare with other 30-50 year olds! I could have really used these for the truth part. I actually asked someone, similar to #5, what is your greatest regret, not realizing how personal it was but she took it well, and I changed it to, something you regret, instead. I have written these down and they will now be in my purse, on hand, for the next time I need them! Thanks, Anne

    Liked by 1 person

    1. Oh my thanks for sharing your day / night with us here, Anne!! And definitely thank you for this awesome comment. That was just sweet 🙂

      One of the things that I find truly amazing about human interactions is how one conversation (might even be super short too!) can have the most drastic impact into lives.

      Remember the first time a teacher or parent gave you a compliment? Wow it was such a powerful moment, was it not? XD

      One of the reasons why I’m so fascinated by social psychology 🙂

      Again, thanks for writing this comment and sharing with every of our readers here on your experience! Feel free to use them and hopefully, change lives for the better with them too 😀

      Your pal,

      Liked by 1 person

    1. Aye npm! I was there before so I totally understand XD

      But do keep in mind, if the other party isn’t as interested in you as you are to them, don’t feel too bad about it and turn your focus to someone else.

      There are three types of ppl I’ve noticed in such situation:

      1. Ppl who are genuinely keen to know more about you
      2. Ppl who genuinely don’t want to; And
      3. Ppl who just simply don’t give a crap no matter who they are with lol

      My point? The problem isn’t always you 😉
      Do your best, know that once your efforts are invested (smartly), time will give you what you deserve.

      If not, you can always come to me or any of us blogging pals! We aren’t going anywhere 😛

      In any case, I definitely hope you will start seeing positive change as you start using these 😀

      If you’ve got questions on anything, do feel free to ask too, yeah? I study psychology so I might be able to help provide some insights for you in terms of socializing, to help you see results faster 😉

      Emailing is always an option for private talks!

      Your pal,


      1. Thanks!

        I am getting to know someone. Over lunch I told him about my views toward other people, but I thought I mentioned the words “money”, “rich”, and “poor” too much; I also think I said some sort of stereotypical thing about “poor people” without explaining why.

        I am afraid that he’d see me as a sort of person who cares a lot about money and status (which I’m not). I am more afraid that because of what I said, maybe I had offended him in some ways and he wouldn’t want to befriend me.

        Liked by 1 person

      2. Well if you mentioned those words too much, there was probably a reason to why you did. Might be due to the circumstances but either way, don’t let me get to you 🙂

        Try to catch yourself when you start to become very self-conscious on what you do, say and how much you care on what people may think of you.

        Would it affect your life that much if this person don’t become friends with you?

        Another question you might want to consider is- Would you want to be friends with someone who judges others so quickly?

        Ultimately, don’t worry too much. Even if this person don’t end up being a friend, there’s always other human beings to approach, yeah?

        Don’t let one bad interaction dictate and seal your fate with future interactions. It doesn’t have to be that away 😉

        Your pal,


      3. Ah alrighty. Well, I’m sure there’s more to it that we aren’t even scratching the surface of it lol!

        After all, we ARE dealing with human interaction. Something very delicate and complicated.

        I hope that whatever I’ve shared can help and definitely hope things will be well for ya.
        I’ll be around if you ever feel like talking/sharing your issues with someone :3

        Your pal,


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