Start a Conversation with Confidence

Silence. It’s the worst. When you’re on a date, it’s terrifying. When you find yourself in a sudden partnership with an acquaintance, it’s awkward. When you’re trying to make small talk with your boss, it’s stressful. If you could just get onto a topic that would get the ball rolling, you would be fine. But somehow, the conversation is coming in short, mundane jolts. Chatting about how troublesome the weather’s been lately is doubtful to lead to more casual, relaxed conversation. So how can you turn this tense encounter into a free, unforced dialogue?

You simply have to ask the right questions. Whether you are on one of your first few dates or meeting your neighbor, the objective is the same. You’re discovering common interests, points of disagreement, and generally getting to know the other person. The best way to learn something about another person is to ask. Small talk is meaningless. To establish a significant relationship, you must develop trust. In order to develop trust, the sharing of information is essential.

The following list can help you extract some relationship building information effortlessly. Some questions are obviously only appropriate in some situations. Use discretion, and don’t get too invasive too quickly. Now the next time you find yourself enduring an uncomfortable silence, you can keep it at bay. Make use of one of these conversation starters to launch banter that could help you find a great friend or boyfriend.

1. When you were young, what did you want to be when you “grew up”? Did you stick to your plan?

2. What cartoon character did you always want to be?

3. What celebrity (if any) do people always say you look like?

4. What has been your biggest challenge to date?

5. How would you define success?

6. If they made a film of your life, who would you want to play you?

7. What is your favorite theme/amusement park ride?

8. Have you ever gotten revenge on someone and why?

9. What is one thing that will cause you to lose respect for me?

10. What do you worry about more than any other thing?

11. What are your feelings about plastic surgery?

12. When you have to cut your budget, what’s the first thing to go?

13. What was the first thing that made you think that you and I should date?

14. What was your first impression of me? Do you think it was accurate?

15. Can you think of an example of a time someone truly betrayed your trust? Did you stay close with that person?

16. What is the most dangerous or stupid thing you’ve ever done?

17. Have you ever lied to me? Why?

18. How would you rank yourself in overall attractiveness? (1 being hideous and 10 being perfect)

19. If you could take over a celebrity’s body, who would you choose and why?

20. What’s a problem that your parents have that you want to avoid?

21. If you had 3 wishes, what would they be?

22. What were your childhood fears?

23. If it’s not a sensitive subject, has anyone close to you ever died?

24. What is your guilty pleasure—you know…something you love but don’t want anyone else to know that you love? (You might want to share yours first. “I like to watch trashy MTV reality shows.”)

25. Who were your best and worst teachers of all time and why?

26. What has been the happiest moment in your life to date?

27. What do you love about yourself most?

28. What has been your most embarrassing experience?

29. Who is your celebrity crush and why?

30. If there was a fire, what three things would you save?

31. What’s the best advice you ever got?

32. What’s the craziest dare you ever went through with?

33. Do you have any personal superstitions?

34. What was your favorite television show as a child?

35. Can you describe your most memorable party experience?

36. What frequency do you think is normal for couples to have sex?

37. Have you ever been in a situation where you thought you were going to die?

38. Have I ever embarrassed you?

39. If you could have any super power, which would you choose and why?

40. If you couldn’t live in the U.S., what country would you call home?

41. Who did you not like in high school and why?

42. What are your favorite places to visit alone?

43. What’s the worst trouble you’ve gotten yourself into?

44. What do you see yourself doing in 10 years?

45. Would you ever skydive or do any kind of thrill-seeking activity?

46. What is your biggest pet peeve?

47. Who has been the largest source of inspiration in your life?

48. If you were stuck on a desert island with only one kind of food, which food would you choose?

49. What are your bad habits?

50. What is the last thing you think about before you go to sleep?

Don’t forget to relate to the other person. Tell them if you have similar experiences. They will be more likely to share if they believe they are in accepting company. Good luck making new friends and establishing new love interests!