It's your lucky day. You won the big game or gave a stellar performance or saved the puppy from the fire. And to honor your accomplishment, now you're being introduced to someone special and famous, and you're going to have a chance to have a private conversation with him/her.

Or, you board the commuter train or go to a noisy cocktail party or take a spin class and suddenly you realize that the person next to you, the extremely attractive guy/gal, is smiling at you and offering to give you some kale chips/buy you a drink/take you out for green smoothies.

In either case, what do you say? How do you overcome your awe and shyness and make a meaningful, lasting impression?

The answer is simple: Ask really good questions.

The Greek philosopher Socrates knew that questions are more engaging than providing information. (His method--ex duco--means to "lead out," as in drawing out knowledge; the term creates a root for the word "education.")

And media interviewers use surprising questions to gain fresh insights into a famous person's psyche. For example, Vanity Fair's Proust Questionnaire causes celebrities to be far more existential than the usual cover story. And my firm uses unusual questions to enliven the usually dull Q&A-style executive interview.

So even if you're not a philosopher or a journalist, you can use questions to break the ice, draw someone out or simply overcome awkward silences. The key is to be unexpected--so that you're surprising and memorable.

To get your party started, here are 31 suggested questions, grouped by handy category:

Which tech?

1. How many unread emails do you have in your inbox?

2. What music track do you listen to most often to?

3. What's your favorite app right now?

4. Which cities do you have bookmarked on your weather app?

5. What is the most unusual photo on your smartphone?

What do you like?

6. If I made you the perfect sandwich, what ingredients should I include?

7. Which food is your favorite guilty pleasure?

8. If you had an unlimited budget and could buy a painting from any artist, who would that be?

9. What book would you recommend for someone taking a long ocean voyage?

10. What's the best movie you've seen this year?

. . . And then what happened?

11. What is the best compliment you've ever received?

12. What is your favorite childhood memory?

13. Have you ever eaten an insect (on purpose)?

14. Have you ever experienced a hurricane, a tornado or an earthquake?

15. Have you ever been in a car, boat or plane accident?

Who loves ya?

16. Who was your best friend growing up? Are you still friends? Why/why not?

17. Which relative are you closest with?

18. Do you have a frenemy?

19. What characteristic do your friends all have in common?

Qui est Marcel Proust?

20. Which living person do you most admire?

21. What is your greatest extravagance?

22. Which words or phrases do you most overuse?

23. Which talent would you most like to have?

24. Which historical figure do you most identify with?

25. What is your motto?

What if?

26. If you could take a three-week vacation, where would you go?

27. If you won the lottery, what's the first thing you would do?

28. If you could have any animal as a pet, what would you choose?

29. If you suddenly became president, what is the first thing you would do?

30. If you could become any age, how old would you be?

31. If you could witness any event of the past, what would it be?

Got it? Start with one question and you'll be pleased by where the conversation can lead.