100 Random Questions You Can Ask to Start a Conversation

100 Random Questions You Can Ask to Start a Conversation

Random questions can be conversation saver for you. Use them wisely and see how you blosso in social situations.


One of the century-old ways of starting a conversation has been to introduce oneself. Most of us start with names, what we do, where we come from, or how we are doing. The conversation goes on but you can change that by asking random questions. 

All of us find ourselves in such awkward moments. They occur at lunch, parties, or gatherings. It commonly happens if you don’t know everyone in the room introducing yourself, complimenting, or sharing a relevant experience.

You feel even more awkward in asking personal questions in the beginning. In such a doubt, you may use your surroundings to create questions to help yourself socially.

Comment on the ambiance. Ask them about their job and hobbies. You can ask general questions, about their favorite music video, or favorite sports team.

Tips that Don’t Require Random Questions

Sometimes, in a situation, introducing yourself gets either too formal or is absolutely unnecessary. In such a situation, the most commonly observed conversation starter is complimenting someone on how they look, how they are doing, or complimenting the ambiance.

Similarly, at times you praise a person or even comment on something pleasant which paves the way to a light and cheerful conversation that takes place eventually. You can lean towards random questions too.

In a group where people generally know you and there’s not much to compliment, you can talk about a shared experience. It can be about travel, food, cars, politics, or sports. You can offer someone help and it can lead to a thorough conversation.

Types of Random Questions to Ask

In order to have a pleasant time socially, we’ve put together a list of random questions to start a conversation. I’m sure you’ll be able to find a few questions that will help everyone have a good time.

These random questions are just the start. It’s up to you to run with the question and take it to the places you find interesting.

Basic Conversation Ice-Breakers

Most of us are really not good at starting a conversation. We make a lot of effort to start an interesting conversation but we end up failing miserably. We make it awkward or we make it boring.

The key is to focus on the basics. Yes, basic questions can really help you. It is the reason we have a list of basic questions which will surely help you in starting an awesome exciting conversation.

  • What is your song of the week?
  • Which song is your all time favourite?
  • Where is the most beautiful place you have been?
  • What is your favourite Netflix season?
  • What is your favourite movie soundtrack?
  • What’s one movie that you can watch repeatedly?
  • What is your all time favourite music band?
  • Your top 3 favourite books?
  • What is one thing you should never say at funeral?
  • What is the best advice you have been given in life?
  • What is the worst pickup line you have ever heard?
  • Are pets better than humans?
  • When scrolling through Instagram, do you prefer celebrity posts or ones from your friends?
  • What is your favourite combination of colours?
  • What one invention would you un-invent and why?
  • What was your favourite bed time story as a child?
  • What is the most annoying habit someone can have?
  • Do you correct people when they make mistakes?
  • Which word do you think is most spoken in the world?
  • What food do you crave more than any other?
  • Which super hero do you look up to most and why?
  • If your food is bad at restaurant, would you say something?
  • What’s the most useful thing you own?
  • What is your favourite thing to eat or drink in winter?
  • Which is more important, having a great car or a great house? Why?
  • What is a language you love to listen to even if you don’t speak or understand it?
  • What do you like more, sea or mountains?
  • Describe the most captivating painting or artwork you have ever seen?
  • When did you get your first smart phone?
  • Do you like it when it snows?
  • Would you rather have the ability to fly or to read minds?
  • What’s the funniest book you have ever read?
  • Do you like horror movies or do they creep you out too much?
  • Are you a cat person or dog person?
  • What colour would you chose to describe yourself?
  • Are you a buffet person? Or do you prefer to order from a menu?
  • Have you ever saved an animal’s life?
  • What is your favourite celebrity scandal?
  • What would you do if you win a lottery of 100 million dollars?
  • What’s the last thing you did for the first time?
  • What do you like to cook the most?
  • Which animated character do you adore the most?
  • If you could close one fast food chain, which one will you pick? And why?
  • Are you a spring or autumn person?
  • What do you prefer, winters or summers?
  • If you are given three wishes what would you wish for first?

Personal Questions

It is not always easy to get a person to open up. People tend to guard themselves and their emotions. However, when they do share, you see a whole new side of them that you have never seen before.

Therefore, asking questions is necessary when you have covered the basics with small talk. You can now jump toward the personal questions. Here is a list of personal questions you can ask to start a conversation.

  • What are the top three things in your bucket list?
  • Would you rather be a master at every musical instrument or fluent in every language in the world?
  • What thoughts instantly make you feel more relaxed?
  • What is the worst present you have ever received and why?
  • Where would you move if you could?
  • Where do you plan to travel next year?
  • Would you rather time travel to the past or the future?
  • What actor or actresses would you want to play you if they ever made a movie about your life?
  • If you were to remove one social media app from your phone, which one will it be? Why?
  • What would be your perfect weekend?
  • What was the best invention in last 20 years?
  • Who is your oldest friend? Where did you meet them?
  • Where and when was the most amazing sunset you have ever seen?
  • If you could trade lives with someone, who would it be?
  • If you had the world’s attention for 30 seconds, what would you say?
  • What is something that really annoys you but doesn’t bother most of the people?
  • Would you break a law to save a stranger’s life?
  • What’s the weirdest thing you have ever eaten?
  • What smells brings back great memories?
  • What’s the best compliment you have ever received?
  • Are you very active, or do you prefer to just relax in your free time?
  • Where do you spend most of your time?
  • What is something you are obsessed with?
  • Do you like spending time alone or with your friends?
  • What is one of your strengths?
  • If you wanted to reward yourself what might you do to celebrate?
  • If you are feeling unmotivated, who helps you get yourself going?
  • What’s more important to you-career or family?
  • Are you someone who plans out their outfits or just puts on whatever you feel like?
  • You get to change your name without having to make everyone learn the new one – what’s the name you pick?
  • Can you pick the 3 words that describe you the best?
  • Where would you like to live in future?
  • If you could only save one item from a house fire, what would it be?
  • If you could do anything illegal without getting caught, what would you do?
  • If you could have a song play every time you enter a room, what would it be?
  • What is something I wouldn’t believe about you?
  • Who in your life brings you the most joy?
  • When are we self improved to accept our selves?
  • What are you proud of, but never had an excuse to talk about?
  • What was the first job you ever had?
  • What is something popular now that annoys you?
  • What trend did you follow when you were young?
  • What talent would you want to possess if you could?
  • Would you rather be a master at every musical instrument or fluent in every language in the world?
  • You are comfortable in working from home or feels like going back to office routine?

Funny Questions

No one prefers boring topics, especially at parties or gatherings. Therefore, we have gathered a bunch of funny questions.

They will surely help you enjoy your time and take your discussions to another level. Have an engrossing conversation with the help of these questions at your parties, dinner table, or even on a long drive.

  • You are now banned from the local library. What would be the reason for it?
  • If you were in a circus, which character would you be?
  • What is the worst advice you have given?
  • What is the silliest thing you have posted online?
  • Would you rather never be able to explain yourself correctly or always have to tell the exact truth?
  • If you could only store one type of food in your pocket, what would you carry?
  • Would you rather give up breakfast, lunch or dinner… forever?
  • Which day do you consider to be the true start of the week, Sunday or Monday?
  • What five things would take with you during the Zombie Apocalypse and why?
  • Would you rather win $10,000 or let your best friend win $100,000?
  • If you were a farm animal, which would you be and why?
  • Have you ever stalked someone on social media?
  • If you became invisible for 10 minutes, what things would you do?
  • If you could make a rule for a day and everyone had to follow it, what would it be?
  • If you were to rule a world for a day, which rule you will amend right away?
  • If you could do anything illegal without getting caught, what would you do?
  • What is the weirdest food combination you have ever tried?
  • If animals could talk which one do you think will be the rudest?
  • Would you rather always say everything that goes in your mind or express in sign language instead of speaking?

Following these lists of random questions, you will be able to start an interesting conversation leading to a healthy discussion.

These questions will save you from awkward silence and you will enjoy talking to everyone around you, be it face to face or over the phone. You will end up enjoying socially.

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