Lets face it, no matter how good a conversation is going, sometimes you’ll get stuck and run out of things to say. This can be especially hard if the person you’re speaking with isn’t keeping up their end of the conversation. Sometimes is seems you have little in common, no shared interests, and no reason to continue speaking with each other. This is usually not the case; some people just need a little kick-start to keep the ball rolling.

Below is a list of forty questions which can help keep things on track, inspire some new directions, and even help you learn a little bit about each other. This isn’t an interview; don’t fire off rapid fire questions like you’re considering hiring this person to be your new personal assistant. These are meant to inspire new conversation topics and open new avenues to help you keep things interesting. Each question, once embarked upon, should also have an interesting follow up from you. For example, don’t ask ‘What do you do for fun,’ listen to the answer and respond with, ‘Hmm.’
These are conversation starters, not conversations.

The next time you are getting ready to go out on a date, go to a party, or even meet up with an acquaintance for a business lunch, peruse this list and find a few questions which you think are interesting and would like to be asked.

1. What did you do on the weekend?
2. Did anything crazy happen this week?
3. What’s keeping you busy right now?
4. How did you fall into this career?
5. Have you seen any good movies (read any interesting books) lately?
6. How do you like to spend your spare time?
7. What do you do for fun?
8. If you could live anywhere in the world, where would it be?
9. Who do you think has been the most influential person in your life, real or fictional?
10. That’s a nice ___, where did you get it?
(note: pair of breasts is not a good substitution in most situations)

11. What kind of music do you listen to?
12. Do you play any sports?
13. What’s your favourite place to eat?
14. Are you interested in ___?
(insert interesting interest of yours)
15. If you could spend an evening with any famous figure from history, who would it be?
16. What would you name your autobiography?
17. What would be the first thing you did if you won the lottery?
18. If you have a choice of super powers, would you rather be invisible, or be able to fly?
19. Do you have any pet peeves?

20. Name one thing you wouldn’t want to live without?
21. What is your favourite movie/book of all time?
22. What would you do on your ideal day off.
23. What is the worst job you can think of?
24. Do you have a lot of friends, or a small circle of close friends/?
25. Would you rather work on a road crew or read a paper in front of 200 peers?
26. What’s your dream car?
27. What’s the most embarrassing thing that’s ever happened to you?
(Remember, if you ask this question you’ll need one as well)
28. If you were granted three wishes, excluding money or another wish, what would you wish for?

29. Do you have any hobbies?
30. Do you play any musical instruments?
31. What is your ideal job situation?
32. Do you have any bad habits?
33. Do you believe in plastic surgery?
34. What was your best subject in school?
35. What makes you really laugh? Do you have a favourite joke?
36. If you had to perform on America’s Got Talent, what would you do?
37. What is your favourite season?
38. Where did you go to school?
39. Name one thing you wish you’d known before entering high school.
40. What is the best piece of advice you have ever heard?