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Unusual questions to ask in an interview, on a first date or to yourself

Patti Stanger and Perez Hilton attends the Match.com Dating Confessions Panel Hosted By Patti Stanger in New York City.
Patti Stanger and Perez Hilton attends the Match.com Dating Confessions Panel Hosted By Patti Stanger in New York City.
Photo by Dave Kotinsky

You might be very surprised what you could learn from asking some off the wall questions. I've hired hundreds of people and interviewed hundreds more for journalistic reasons over the years and get the most insight from questions and conversations not normally asked.

A fun part of a first or second date is to ask 20 such questions. Here are some I have used in interviews, life coaching, happiness coaching and on first dates. Answer for yourself for self discovery.

1. What five U.S. cities would you never, ever move to even for the job offer of your dreams? Why?

2. What combination of fixings makes your perfect burrito?

3. If you had a choice of a superpower, to turn invisible or fly at will, which would you choose and why?

4. Do you have, or have you ever had, any nicknames? How did you get them?

5. What’s one thing you wish you had known at age 15?

6. Do you consider yourself a morning person or a night owl?

7. What do/did your parents do for a living?

8. Name four bucket list items?

9. Were you closer with your mom or your dad growing up? Why?

10. Where is your happy space?

11. What are you worse at than 90 percent of the population?

12. Do you believe in ghosts?

13. Where is the most favorite place you have traveled?

14. What fact about you surprises people the most?

15. What is the most embarrassing thing that has happened to you?

16. What’s the most spontaneous thing you’ve ever done?

17. What’s your ideal three-day weekend?

18. If you could live in any other U.S. city, besides the one you do now, which city would you live in?

19. What was your favorite family vacation growing up?

20. What are you better at than 90 percent of the population?

21. If you could travel back to any one point in time what would it be?

22. What is the sixth most proudest moment or greatest achievement of your life so far?

23. How did you meet your best friend?

24. Who was your favorite teacher or professor?

25. What’s the luckiest thing that’s ever happened to you?

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