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30 Conversation Starters For Date Night

The last thing you want on a first date is to run out of things to talk about. Awkward silences are not great for finding out about someone, letting yourself shine, or even (hopefully) igniting some passion.

The trouble is, there are so many cliched questions that can just seem tired, tedious, or simply played out. This is especially true if you have been on a few dates lately. On the other hand, a well-placed and thought-provoking question can get the conversation flowing and help you to stand out too.

So, before you go on your next date, check out this list of questions for some inspiration. Of course, you don’t have to remember them all and feel free to say them how you would say them too:

1. What really makes you laugh?

2. What is something you wish you did more of in your life and something you wish you did less of?

3. If you won the lottery, what is the first thing you’d do with the money?

4. What’s one fear you know is holding you back?

5. What’s your favorite book?

6. What piece of advice would you give to your younger self?

7. What’s your favorite place in the entire world?

8. What’s something many people fear that doesn’t scare you at all?

9. If you had to name one thing that really makes your day, what would it be?

10. Who has been the biggest influence on your life?

11. What accomplishment are you really proud of?

12. What’s your favorite way to spend the weekend?

13. What day would you love to relive?

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

15. What do you hate most about dating?

16. What’s on your bucket list?


17. What are you most excited about in your life right now?

18. What is the most thoughtful gift you’ve ever received?

19. What’s your favorite thing about your job?

20. What do you wish more people realized about you?

21. Is there anything you’ve always wanted to try?

22. How many times have you been in love and what did the experiences teach you?

23. What’s one of your favorite childhood memories?

24. What’s the stupidest thing you’ve ever done for love?

25. Do you consider yourself spontaneous, or a planner?

26. Can you think of anything that comes easier to you than it does for most?

27. What quality is an automatic ‘no’ when it comes to your relationships?

28. What was the worst job you’ve ever had?

29. When you were a kid, what did you hope to do when you grew up?

30. What was the last thing you learned that made a big impact on you?

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