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First Date: 15 Questions to Break the Ice

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First dates are exciting, but they can also be downright nerve-wracking. You want to be charming and intelligent. Oh, yeah… funny would be good, too.

That’s a lot of pressure. We all know awkward silences are the worst.

I’d like to help you out before that next big dinner or coffee by offering some creative first date questions you can use if you need to stir up conversation.These questions come from dating coach/matchmaker Rachel Greenwald’s, “Have Him at Hello: Confessions from 1,000 Guys About What Makes Them Fall in Love…or Never Call Back” (© Random House 2008). If there’s a lull in the conversation, insert a creative question or two and the conversation should begin to flow.

No worries; you don’t need to remember all of them! Just pick one or two to get things going.

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

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 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?

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?

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