10 Interesting First Date Questions

First Date

A friend of mine recently went on a first date. Being a Matchmaker and constantly submersed in all things dating, she naturally turned to me for advice about first date conversation.

Asking questions and being genuinely interested in the response is always my number one dating tip. However this got me wanting to think outside the box. So I decided to put together my Top 10 first date questions to keep conversation a little more interesting.


1. What is the best compliment you’ve ever received?

2. Describe your best holiday experience?

3. What is the first thing you noticed about me?

4. How would you spend 10 million dollars?

5. What are you determined to have or create in your lifetime?

6. Describe the most embarrassing moment in your life?

7. What habit are you most proud of breaking?

8. Who do you most admire in your life and why?

9. What’s the best advice you’ve ever received?

10. If you could invite any 3 people to dinner, alive or dead, who would they be?


Take turns answering each question, and …

Best case scenario? You’ll be feeling a rush of invisible glitter-butterflies.

Worst case scenario? You’ll hear a few amusing stories, learn something new, and maybe realise a few things about yourself too.


Truth be told there are a lot more I could have included. But I would prefer to hear what interesting questions you would like to ask on a first date.




About Karen Von Blanckensee

Karen’s love of matchmaking was ignited the first time she successfully set up some friends. By combining this passion with her experience in sales, marketing & event management, Karen delivers the best possible solutions for her single clients. When she is not busy happily bringing singles together, spending time with family and friends is a joyful priority.

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