35 of the Best Ice-Breaking Questions for a First Date

Have you ever been stuck in that awkward silence on a first date…

Where neither of you can figure out how to fill the gap, except to offer something lame like:

So, what do you do for fun?”

Can you guess how many times he’s been asked that question? (Hint: probably the same number as you!)

Most men form their opinions about a women within 10 minutes of the date—women give it 60 minutes—so you want to stand out from the crowd.

Don’t waste those crucial minutes by asking typical questions like:

What do you do for work?”

What do you like to do in your free time?”

If your goal is to find out more about him, those questions aren’t going to elicit the most insightful answers.

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

Ask him questions that get him thinking. Ask him questions that reveal more than he probably wanted you to know! And have a ton of fun while doing it.

To get you started, here are my top 35 ice-breaking questions for the 1st (or 40th!) date.

Top 35 Ice-Breaking Questions for a First Date

1. Which 3 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 ever?
7. Where would you like to be in 5 years’ time?
8. If money was not a concern, what would you do every day?
9. What is the best/worst/cheesiest pickup up line you’ve heard or said?
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 3 guests be?
17. It’s Saturday morning. What’s the first thing you do when you wake up?
18. If you could go back in time and give your teenage self one piece of advice, what would it be?
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 ever met?
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 or go to the movies by yourself?
26. If you could snap your fingers and appear somewhere else, where would you go?
27. Would you rather find true love or win $10,000,000 dollars?
28. Would you rather be rich and ugly … or poor and beautiful?
29. Would you rather date someone who is 10 years younger than you or someone who is 10 years older?
30. Would you rather marry someone who your parents chose for you or spend the rest of your life single?
31. Would you rather be the funniest person in the room or the most intelligent?
32. Would you rather win $50,000 or let your best friend win $500,000?
33. Would you rather have a baby at 15 or a baby at 65?
34. Would you rather live in space or under the sea?
35. Would you rather lose your sense of touch or your sense of smell?

I’m sure you know this already, but please don’t pull out your phone, pull up this article, and read out these questions to your date!

Instead, read through this list before the date and notice which ones seem most interesting to you. Insert them into the conversation in a natural way.

That way, you’ll come across as bold, confident, and unlike any other woman he’s met before.

P.S. Does the thought of asking him these questions make you nervous? Then try Your Brilliance expert author James Bauer’s tips for beating first-date nerves.