35 of the Best Ice Breaking Questions for the 1st Date

Are you one of the 124.6 million U.S. adults who are single? 

And if so, have you ever been on a first date?

Have you ever been stuck in the awkward silence where neither of you can figure out how to fill the gap of words…

Except for something really lame like:

So, what do you do for fun?

Let’s be real.

Being captivating on the first date is super important. 

In fact, most men form their opinions about a women within 10 minutes of the date. Women give it 60 minutes.


So that means you don’t have too much time to make a great impression. 


Don’t waste it with typical questions like:

What do you do for work? 

What do you like to do in your free time? 

These questions are boring and honestly won’t give you too much insight into who this person is and if their ‘waters run deep’ so to speak.

Why not, instead, be the date he can’t forget!? 

Why not leave your date wanting more!?

Why not be smart and white and clever while also getting to know the person sitting across the table from you!? 

35-ice-breakers - first-date


Without further ado, here are my top 35 ice breaking questions for the 1st (or 40th!) date! 


1. Which three words describe you best?

2. What’s the best thing that’s happened to you this week?

3. What did you want to be when you grew up?

4. What is the longest word you know?

5. What is the best praise or advice you’ve received?

6. What was your favorite birthday or Christmas present?

7. Where would you like to be in five years time?

8. If money was not a concern what would you do every day if you didn’t work?

9. What is the best/worst/cheesiest pickup up line you’ve heard or said or had been said to you?

10. What do you think about chick flicks and which was the last one you saw?

11. Who’s the person in your own life you admire most?

12. What do you hate most about meeting someone on a first date?

13. What is the most expensive thing you have ever bought?

14. Were you closer to your mom or your dad when you were younger?

15. What would your closest friends tell me about you?

16. If you had your own talk show, who would your first three guests be?

17. It’s Saturday morning. What’s the first thing you do when you wake up?

18. If you could have been told one thing that you weren’t told when you were a teenager, what would you like to have heard?

19. What do you keep in the trunk of your car?

20. What’s the most romantic place you’ve ever visited?

21. Who is the most famous person you’ve had a face to face encounter with?

22. If you knew you could not fail, what would you do?

23. If you could be invisible for a day, what would you do?

24. What’s your biggest pet peeve?

25. Can you comfortably eat in a restaurant by yourself? Go to a movie?

26. If you could snap your fingers and appear somewhere else, where would you be?


Would you rather….

27. Find true love or win 10 million dollars?

28. Be rich and ugly or poor and beautiful?

29. Date someone who is 10 years younger than you or someone who is 10 years older?

30. Marry someone who your parents choose for you or spend the rest of your life single?

31. Be the funniest person in the room or the most intelligent?

32. Win $50,000 or let your best friend win $500,000?

33. Have a baby at 10 or a baby at 60?

34. Live in space or under the sea?

35. Lose your sense of touch or your sense of smell?


Now obviously it goes without saying, don’t simply pull out the piece of paper and read off the questions to your date.

Have these questions in the back of your mind and use them to get the conversation flowing and to find out more about this stranger in front of you.

Otherwise, the date can get real awkward real fast.

And your date will NOT look back on the date as memorable and be licking his/her chops to see you again!

Instead, date with confidence. Be a little silly and sassy and allow your true personality to shine through!


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