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15 Creative Questions to Ask a Date


Check out this list to see some things that can get your date started on the right foot.

By Certified Professional Life and Dating Coach, Sandy Weiner, for

Are you ever at a loss for words on a first date with a virtual stranger? You’re not alone!

Unless you’re endowed with the gift of gab, you and your date might end up in a staring contest, while you listen to the crickets in the background. Okay, it might not be that bad for you. But trust me, it’s not always easy to be clever when you’re nervous.



I’d like to help you out before that next big dinner or coffee by offering with some creative first date questions you can use if you need to stir up conversation. Use one or two on your date, and the conversation should begin to flow.

You can also use one of these questions in your online email correspondence. Asking a question in an email will increase your chance of hearing back from someone you have your eye on!



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1. What’s a secret skill that you have?

2. What was your favorite childhood toy?



3. What’s the best present you ever gave someone?

4. What’s the most embarrassing thing that happened to you in elementary school?



5. If your house was on fire, what’s the first thing you’d grab to save?

6. What’s your dream travel destination?



7. When you were little, what did you dream of being when you grew up?

8. What’s one of your favorite books/movies? Why?



9. What was your worst job?

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10. What’s the best advice anyone ever gave you?

11. Growing up, what was your favorite board game?


12. If you could live anywhere, where would it be?

13. What was your best birthday ever?



14. What’s the bravest thing you’ve ever done?

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


What questions would you add to this list?

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This article was originally published at . Reprinted with permission from the author.


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