Best Questions To Know Someone Better

The most likely questions you encounter while communicating with someone new are; “What do you do?”, “How you doing?”, “How’s it going?”and so on. These kind of questions can make you feel awful and definitely aren’t the best questions to know someone better.

So, you struggle to answer, not even sure if the asker cares in the first place, or if it’s just small talk.

Why does it have to be like this? And why do we care so much about what someone does, anyway? Hopefully, we respect ourselves enough to know that we are dynamic people who can’t be described adequately in one sentence. We also know that we can’t get someone to feel invested in us, or our work, in a quick transactional conversation.

Isn’t there a better way? Yes, but you may have to break a few norms to bust up the status quo to really get to know someone. 

Here are some questions you might want to try in your day to day life. I’ve categorized them into mild, medium and hot so you can go deeper as your palate allows.


  • Any upcoming travel plans?
  • What brought you here?
  • How do you two know each other?
  • When you’re not working, how do you like to spend your time?
  • What are you reading currently?
  • What’s the first concert you attended?
  • Where do you most hope to visit?
  • What’s your favorite book?
  • What’s your favorite show?
  • What’s the best Halloween costume you’ve ever had?
  • What’s your dream job?
  • What’s your favorite word?
  • What was your first job?
  • What’s one thing you’re excited about that’s coming up in 2018?
  • What was the worst job you’ve ever had?
  • What is your most-used emoji?
  • If you could win an Olympic medal for any sport, real or fake, what would it be?
  • If you could change your name, what would it be?
  • What movie or TV show title best describes your week?
  • What was your favorite subject in school?
  • What’s your hidden talent?
  • If you had to eat one thing for every meal going forward, what would you eat?
  • If someone were to play you in a movie, who would you want it to be?


  • If you could spend a day in someone else’s shoes, whose would they be? Why?
  • What’s one thing your mother/father taught you that completely changed your life?
  • What’s been on your mind lately?
  • What’s the first career you dreamed of having as a kid?
  • What’s the last text you sent?
  • What’s one of your favorite memories?
  • What’s one thing about you that surprises people?
  • Who, or what, was your biggest teacher?
  • What was something you’ve done that made you feel extreme happiness?
  • Knowing what you know now, what advice would you give your 18-year-old self?
  • If you could instantly become an expert in something, what would it be?
  • What does success mean to you?
  • What’s the best piece of advice you’ve ever been given?
  • Where is your happy place?
  • If you could invite 3 people, dead or alive, to a dinner party, who would they be, and why?
  • How can someone win a gold star with you?
  • What energizes you and brings you excitement?
  • What qualities do you value in the people with whom you spend time?
  • For what would you be famous?
  • What does your dream day look like?
  • If you didn’t have to sleep, what would you do with the extra time?
  • What’s your guilty pleasure?
  • At what job would you be terrible?
  • If you had to choose only 3 adjectives to describe yourself, which would you choose?


  • What do you give a damn about?
  • What is a dream you have that you’ve yet to achieve?
  • What’s something you say you’ll do, but never will?
  • What did you have to give up to achieve your current level of success?
  • Has anything ever happened to you that you could not, and cannot, explain?
  • Do you ever find there are things about you that people misunderstand? What are they?
  • For what are you most grateful today?
  • If you could have one ‘do over’ in your life, what would you do differently?
  • Of what are you most afraid?

You need to keep in mind that you should never overdo these questions.

Listening is equally important and requires discipline. It helps you properly analyse how your conversation partner responds and if they are willing to break the mold of their typical conversation patterns.

Always, follow the course that the conversation takes. Any questions that come after should be a natural follow up to their response.

It takes time to build a relationship. The initial interaction should be used to find some chemistry and build rapport. Choose any of these questions to have in mind for your next interactions, and see what feels authentic to you in kickstarting new relationships.

And then, you will eventually get to know what someone does. No need to lead with it. Ideally, it will uncover itself as you get to know what really matters to your new friend.

A version of this article appears on Forbes. | Author: Darrah Brustein (@DarrahB)

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