21 Fun Questions To Ask Someone On A Date

Questions are the most interesting things that we can come up with when we want to learn about someone else.

Dale Carnegie in his amazing must-read book, “How to win friends and influence people” shares about the simple power of asking good questions to show that we are interested in someone else.

Have you been to a party and been the one asking all the questions and doing all the listening? If you have, you will most likely agree that the other person thought that the conversation was quite interesting. You probably did less that 20% of the speaking but you got 100% of the credit!

If you are a guy and ask careful questions from a lady, you will often find yourself jumping to last-base, thus saving yourself a lot of legwork trying to build rapport with her. Asking questions and listening is one of the most naturally flattering things you can do to anyone.

If you are a lady and want to stroke a guy’s ego and make him feel good then ask lots of interesting questions and then listen to the answers. You will have the guy on a string from there on!

Despite the ego-focused side of asking and listening there is a genuine side as well. Because the people who are genuinely interested in someone else and ask great questions are the people who are always popular and well liked. Faking interest is the worst thing you can do. And at the end of the day, if you are not a natural listener then put yourself to the test and practice. You will start to learn SO much about so many things and you will discover parts of people that are just SO interesting to learn about.

Here are 21 questions to ask to get the conversation rolling. They have been written from a female perspective, just switch them around if you are a guy and want to use them. If nothing else it will get you thinking about your own questions – which are always better.

Here’s 21 questions to ask a guy or a girl to get you started

1. If you’re a waiter and a customer was super rude, would you spill food accidentally on them or think about doing this?

2. What was your favourite Halloween dress up costume as a child and why?

3. If you had the chance to choose 5 people to invite to dinner – real of fictional – who would you invite and why?

4. If you could suddenly become the invisible man, where would you go and what would you do?

5. If someone made a funny comedy movie about your life, which part of the story would be the funniest and why?

6. What was your fondest television character when you were a young child? What was it that you liked about them?

8. What do you regret not doing the most in your life?

8. What’s the most hilarious experience you’ve had in your entire life?

9. Have you ever had a date with a person that is much fatter or slimmer than you and when you saw them for the first time what did you think?

10. What age were you when you had your first proper date and did you get to kiss them?

11. What was the worst lie you have ever told in your life? Did you get caught out?

12. If you instantly turned into a woman just for a day, what would you do with your day and why?

13. When you meet someone for the first time and you do not like them what would you normally do?

14. What is more important to you in a woman – good looks or intelligence?

Time to get a little more personal! Maybe you should wait till you have had a few more drinks before asking some of these!

15. Have you ever been caught with your pants down in a public place – if so what were you doing?

16. What’s the difference between having sex and making love for you and which do you prefer?

17. If you could suddenly change the age you lost your virginity, would you?

18. What’s your biggest sexual ‘turn-ons’ and ‘turn-offs’?

19. Have you ever been unfaithful to your partner and did they find out? If so, what happened?

20. Have you ever been caught masturbating? If you did, how old where you and who caught you?

21. Have you ever serial sex – with one person and then been with a different person somewhere else within the same day?

If you would like to read more fun questions that you can ask different guys then visit 21 questions to ask a guy today.

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