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Turn small talk into real talk.

Getty Images Tara Moore

You know how sometimes when you meet someone, you click almost immediately, and it feels like you've been besties your entire life? And then, there's those other relationships that take a little more work (i.e., how you have to pulling pull to learn anything about your brother-in-law?). While you might never be BFFs with your BIL, there is a trick you can use to get him to open up a little more.

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Terri Orbuch, Ph.D., author of 5 Simple Steps to Take Your Marriage from Good to Great, says getting to know someone starts with the “breadth questions”—think: impersonal but important biographical info like where someone is from, where they work, if they’re single or married, etc.

To really get to know someone beyond the surface level, you’ve got to start going deeper. “Topics that get at the other person's inner world—their thoughts, goals and dreams—will strengthen and increase bonding between two people,” Orbuch says. “Just like in a romantic relationship, sharing personal information strengths the relationship—deeper questions focus on that personal self-disclosure.”

Move past the small talk ASAP, and ask these 41 questions instead:

“Asking someone about their preferences helps you to understand who they are as a person,” says Rebecca Hendrix, a therapist in New York. The important thing here is to go deeper by asking follow-up questions.

For example, “if you find out they like dogs, take it a bit deeper by asking them what they like most about their dog,” Hendrix explains. “In answering, they are revealing a little more about themselves.” Some other ideas:

1. What’s your favorite way to spend a weekend?

2. What type of music are you into?

3. What was the best vacation you ever took and why?

4. Where’s the next place on your travel bucket list and why?

5. What are your hobbies and how did you get into them?

6. What was your favorite age growing up?

7. Was the last thing you read digital or in print?

8. Would you say you’re more of an extrovert or an introvert?

No matter how a person feels about his or her job, the fact is, we all spend a lot of time and energy at work. To help you get to know someone better, “facilitate a conversation where you are left knowing how they feel about their career,” Hendrix says. For example:

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9. What’s your favorite thing about your current job?

10. What annoys you most?

11. What’s the career highlight you’re most proud of?

12. Do you think you’ll stay at your current company awhile? Why or why not?

13. What type of role do you want to graduate to after this one?

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15. Does your job make you feel happy and fulfilled? Why or why not?

16. How would your 10-year-old self react to what you do?


A great way to get to know someone on a more personal level? Learn about the people they love. “Asking questions about close relationships can lead to stories, and sharing stories leads to connection and an experience of being seen by one another,” Hendrix explains. Try:

17. How much time do you spend with your family?

18. Who do you most like spending time with and why?

19. Were you close with your family growing up?

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21. What traits are most important to you in your family members?

22. Who are you the closest to and why?

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“In learning about someone’s values, you are learning about their owner’s manual,” Hendrix explains. Even seemingly mundane questions can get at a person’s values—like what’s motivating them to do well on a presentation or what they look for in an S.O. “By learning about someone’s life philosophy, you're able to get at their true essence, how they live their life, and what drives their actions,” Orbuch adds.

That said, you can't just ask, "What are your values." What you can ask:

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24. What’s a relationship deal breaker for you?

25. If you had only one sense (hearing, touch, sight, etc.), which would you want?

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27. Are you at all religious or spiritual?

28. What are you most proud of in the last year?

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30. Who do you admire most in the world?

31. If you won a million dollars, what would you do with the money?


“These questions get at what the person is motivated by,” says Orbuch. “What gives them the strength to wake up every day and get going? What do they dream and think about in their day?” When you learn about someone’s dreams, you share something more intimate.

32. If you could do anything, besides what you're doing now, what would you do?

33. What do you regret not doing in the last year?

34. What’s on your bucket list?

35. If you had unlimited money to start your own business, what would it be?

36. If you found out today was your last day on Earth, what would you do?

Unconventional questions

Sometimes the oddball questions allow you to learn the most interesting things about a person. “Unusual questions allow you to see the varied, unique and special qualities of a person—their answers give you personal information about what makes them tick,” Orbuch says. “These questions also typically get the other person to think outside box and really ponder something.”

37. If you see a puddle on the ground, do you walk around it or over it?

38. If you could have a super power, what would it be?

39. If you could go back to anytime in history, where would you go?

40. If you came back in your next life as an animal, what animal would you be?

41. If you got to name a new country, how would you decide what to call it?

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42. What would be the title of your memoir?

“Anytime you reveal personal information to someone else, it increases intimacy between you and the other person,” says Orbuch. So let down that guard yourself, and don't be afraid to ask (or answer!) those deep questions.

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