AnnaMarie Houlis
Journalist & travel blogger

Sometimes conversations can feel like pulling teeth. It's not always easy to keep the talking flowing organically, and long, awkward pauses can seem to drag on forever.

Here are 75 conversation starters to ask in different scenarios in order to keep the chit chat coming.

At a networking event

1. What does your company do?

2. What line of work are you in?

3. How did you end up in the job you're doing now?

4. What experience had the biggest impact on your career?

5. What would be your dream job?

6. What is your biggest career aspiration?

7. What's been your biggest career accomplishment thus far?

8. Who has been the most inspiring person in your career?

9. How did you land your first job?

10. What kinds of people do you prefer to work with?

At work

11. What's on tap for you today?

12. Are you working on any new, exciting projects?

13. How is your week treating you?

14. How do you practice self-care?

15. How do you get your work-life balance?

16. What are your career goals?

17. What did you do in your last job?

18. What's your background in?

19. What inspires you to do the work you do?

20. Who in your life has had the biggest impact on your career?

At a party 

21. What did you do last weekend?

22. What are your plans for this upcoming weekend?

23. What's the last vacation you took?

24. Do you have any upcoming vacation plans?

25. How do you prefer to spend your free time?

26. Where have you always wanted to visit if time and money were unlimited?

27.  Do you consider yourself an introvert or an extrovert, and why?

28.  Who is your favorite sports team?

29. Where do you typically hang out?

30. What does your ideal night out look like?

On a date

31. What do you do for a living?

32. How do you spend your free time outside of work?

33. What is your family like?

34. What's one place you've always wanted to travel to?

35. What was your warmest childhood memory?

36. What was the best concert you ever went to?

37. What's the biggest thing on your bucket list right now?

38. What are your friends like?

39. What's your favorite meal to cook?

40. Where is the most beautiful place you've ever traveled?

Meeting a friend or SO's family

41. What's your favorite family memory?

42. What was the best vacation you ever took together?

43. Where do you want to travel together as a family?

44. What are your favorite family meals?

45. What's your best family tradition?

46. What does your family like to do together?

47. How did your parents meet?

48. Did you have any pets over the years?

49. How big is your family?

50. How often are you able to get together?

During an interview

51. What would you say are the most important qualities in someone for this role?

52. Can you describe the culture of the company?

53. What are the biggest opportunities facing the company right now?

54. What are the biggest challenges the company is facing right now?

55. What do you like best about working for this company?

56. Where do you think the company is headed in the next few years?

57. What is the typical career path for someone in this role?

58. What does a typical day look like at this company?

59. What experiences lead you to work for this company?

60. What skills do you find most important to do this job well?

Meeting someone new

61. Do we have any friends in common?

62. How do you like to spend your summers?

63. What's your favorite season?

64. What is your hometown like?

65. What was your childhood like in your hometown?

66. What are your hobbies?

67. How do you typically spend your weekends?

68. Are you a morning person or a night owl?

69. What do you do for work?

70. What genre of music do you prefer?

At School

71. What are you studying?

72. What classes are you taking this semester?

73. What is your favorite class right now?

74. What professor has had the biggest impact on your college career?

75. How do you spend your time outside of class?

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AnnaMarie Houlis is a feminist, a freelance journalist and an adventure aficionado with an affinity for impulsive solo travel. She spends her days writing about women’s empowerment from around the world. You can follow her work on her blog,, and follow her journeys on Instagram @her_report, Twitter @herreportand Facebook.