15 Creative First Date Questions

Posted by in communication skills in dating, first date success, single women over 40 | 0 comments

first date questionsEver 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 crickets chirp in the background. Okay, it might not be that bad, but it’s not always easy to think of what to say when you’re nervous. I’m helping you out with some creative first date questions. These questions are by Rachel Greenwald, author of “Have Him at Hello” by Random House . 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 increases your chance of hearing back from a guy.

15 Creative First Date Questions

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 fantasy 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?

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?

Can you think of any questions to add to the list?




  1. 5 Tips For Dating Success In Midlife | Finding Love Again - […] and sharing too much personal information too soon. Instead, focus on your date. Ask a lot of fun questions…
  2. 5 First Date Questions You Should NEVER Ask - - […] written many articles about creative questions to ask on a first date to help you spark a meaningful conversation. The right…

Leave a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.