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20 Interesting Questions to Ask Someone to Get to Know Them

20 Questions to Ask Someone to Get to Know Them
Many times you find yourself in odd situations wherein you meet a new person and you don't really know what to say to them or how to start a conversation. An ideal thing to do in such a scenario is to get to know that person better; the easiest way to do that is to ask questions.
Abhijit Naik
Last Updated: May 31, 2018
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Every individual is different. For those who aren't really comfortable starting and steering a conversation, that is exactly where the problem begins. How are you expected to get to know a person well if you find it difficult to even start a conversation with someone? Let alone with different people, each having distinct personalities. The answer is quite simple, really - you ask them questions.
That way you get them talking and before you know it, you'll not only be having a decent conversation with them, but getting to know them as well. So what are the kind of questions that you can ask them?
About Themselves
Here's the golden rule to any great conversation - ask people questions about themselves and they'll get going like a high-speed train. Instead of asking the common ones like 'What's your favorite color' or 'What kind of music do you like', ask something quirky!
searching something
  • What is the one thing that you love the most about yourself?
  • If you were to change one thing about yourself, what would it be?
  • What do you appreciate most about your life?
  • What do you like to do in your spare time/on weekends?
  • What are the 5 important things you would include in your things-to-do list?
  • Do you have any regrets in life?
Random Questions From Here and There
Here are two types of personal questions - the direct personal questions that demand direct answers and the subtle personal questions that seem fun and random, but allow you to know a person quite well.
Riding bicycle
  • Have you ever been so drunk that you have not remembered anything of the previous night?
  • Would you flirt with a professor of the opposite sex to get a higher grade?
  • Would you ever go skydiving/bungee jumping/deep sea diving/paragliding?
  • 15 hours of a train journey through a scenic route or a 1 hour plane journey?
  • If you were stuck in an elevator with your childhood idol/crush/boss, how would you react?
  • Would you cover a hickey or flaunt it?
And Some About Love and Marriage
The subject of love and marriage is something that is quite close to everyone's heart. These questions are really deep and personal. So make sure that you have achieved some sort of comfort level with the person before asking such questions.
spending time together
  • What's the first thing you notice about a person of the opposite sex?
  • Are there any specific personality traits you would like to see in your life partner?
  • Do you see yourself getting married in the next few years?
  • Would you marry your partner if you knew they were suffering from a fatal disease?
  • What is that one thing that would be a deal-breaker in any relationship for you?
While all these questions will definitely help you to start a conversation with someone, and get to know them better, it is very important that you ask them in the correct manner. You can't just start off with questions about love or relationships as the person might feel that you are invading their personal space. The fun random questions would work well with someone you have just been introduced to, while the personal questions will require you to have established some sort of rapport or comfort level before you ask them.