Beware of monotony; its the mother of all the deadly sins

Sometimes, you meet someone, and you just click. You feel like you've been besties your entire life and honestly can't believe there was a time when you didn't even know they existed. And then, there's those other relationships that take a little more work—i.e., how it feels like pulling teeth 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.

Terri Orbuch, PhD, 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 about a person's family, their career, and if they’re single or married, for example. (Although if you're asking these q's of your BIL... you should probably definitely know the answer to that last one.)

Tamekis Williams, LCSW, founder of Mission Dorothy Female Empowerment Services, adds that you want to ask open-ended questions that will allow the other person to elaborate, instead of questions that can be answered with a simple "yes" or "no."

Some other ideas:

1. https://www.guest-articles.com/anime/the-36-questions-that-lead-to-love-07-03-2021

2. https://www.thewyco.com/general/everyone-lives-by-selling-something-07-03-2021

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?

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

9. What's your favorite ice cream topping?

10. What was the last TV show you binge-watched?

11. Are you into podcasts or do you only listen to music?

12. Do you have a favorite holiday? Why or why not?

13. If you could only eat one food for the rest of your life, what would it be?

14. Do you like going to the movies or prefer watching at home?

15. What’s your favorite sleeping position?

16. What’s your go-to guilty pleasure?

17. In the summer, would you rather go to the beach or go camping?

18. What’s your favorite quote from a TV show/movie/book?

19. How old were you when you had your first celebrity crush, and who was it?

20. What's one thing that can instantly make your day better?

21. Do you have any pet peeves?

Questions can help deepen any relationship, but you should never have to ask these ones if you're in a healthy relationship:

Do You Love Me? Questions You’ll Never Have To Ask If You Are In A Healthy Relationship
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22. Which meal is your favorite: breakfast, lunch, or dinner?

23. What song always gets you out on the dance floor?

24. When you were a kid, did you eat the crusts on your sandwich or not?

25. What activity instantly calms you?

26. Ideally, how would you spend your birthday?

27. What do you do on your commute to/from work?

28. Do you have a favorite type of exercise?

29. What's your favorite season and why?

30. What's the best joke you've ever heard?

31. What's the phone app you use most?

32. Would you rather cook or order in?

33. Have your ever disliked something and then changed your mind?

34. What's your favorite board game?

35. How do you take your coffee?

36 What's your most prized possession and why?

37. Is there any product that you couldn't live without?

38. Do you sleep with a top sheet? Why or why not?

39. If you could have any exotic animal as a pet, which would it be?

40. What would be the first thing you'd do if you won the lottery?

Career

No matter how a person feels about his or her job, the fact is, tons of people 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.

Just prepare yourself to return that openness when they ask the same of you and your work life. "Initial conversations set the tone for if the person wants to continue to get to know you, so be ready to answer some questions as well," Williams says.

Try out these convo-starters:

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

42. What annoys you most?

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

44. Do you think you’ll stay in your current gig awhile? Why or why not?

45. What type of role do you want to take on after this one?

46. Are you more of a "work to live" or a "live to work" type of person?

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

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

49. What do you remember most about your first job?

50. How old were you when you started working?

51. What’s the worst job you’ve ever had?

52. What originally got you interested in your current field of work?

53. Have you ever had a side hustle or considered having one?

54. What’s your favorite part of the workday?

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55. What’s the best career decision you’ve ever made?

56. What’s the worst career decision you’ve ever made?

57. Do you consider yourself good at networking?

58. What career advice would you give to your younger self?

59. Do you believe in having a "five-year plan"?

60. How do you separate your work life from your home life?

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61. When will you know you've "made it"?

62. Are you looking forward to retiring, or do you plan to work as long as possible?

63. Have you ever had "imposter syndrome"?

64. What do you think about workaholics?

65. What qualities do you look for in a boss?

66. Do you have a professional mentor? If not, do you want one?

67. Do you have a work best friend?

68. Are you into after-work happy hours?

69. How do you motivate yourself in your career?