Attracting men

What To Ask a Guy in 21 Questions

Misty Thomas
By Misty Thomas. Updated: February 25, 2021
What To Ask a Guy in 21 Questions
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Really getting to know a new guy can be quite difficult. Any time you start a new relationship or even just a friendship, there is a bit of an awkward phase. There are ways that you can get through this awkwardness and get to know someone better, and one great way is to play the game 21 Questions. The idea of this game is that you have to pick 21 questions which the person must answer truthfully. Of course, you should pick questions that will help to reveal the persons beliefs, desires, fears and ambitions as much as possible, as the whole idea is to get to know them better - so you should choose your questions carefully! is here to give you some ideas about the best 21 questions to ask a guy to get to know them better. These questions will not only help you get to know him, but he can also ask them to you in reverse so you can open up to him as well.

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  1. Start with the basics
  2. The much deeper questions
  3. More great questions for 21 Questions

Start with the basics

If you're not sure where to start, you can always ask him a handful of questions and see where it goes from there. There are about 8 basic questions that you can ask him when you two sit down to play the game.

1. What is his favorite movie/band/sport and why?

2. What does he want to do for a career?

3. What is his favorite animal and why?

4. What is his favorite color?

5. What is his favorite food or dish?

6. What is his favorite out of beer, coffee, or wine of choice?

7. How many siblings does he have?

8. What is his most prized possession?

These are a few basic questions that can easily start up a good conversation.

The much deeper questions

There are plenty of great questions you can ask a guy and after the two of you have loosened up a little, those deeper questions will come out. If you are unsure about which deep questions to ask, we have 8 suggestions for you.

9. What was his first girlfriend like?

10. When did he first kiss a girl?

11. When was the first time he had sex?

12. When was the first time that he had his heart broken?

13. What does he think is the sexiest thing about himself?

14. If he had a chance to go back in time, would he go back to his first date?

15. What is the one thing that he wants to change about himself?

16. What are his relationship goals from now on?

What To Ask a Guy in 21 Questions - The much deeper questions
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More great questions for 21 Questions

When things start to warm up, now you can ask him some playful questions that may spark up a lot of interest. Remember, he is allowed to turn these questions around on you at any time, so if you don't want to have to answer it yourself, be careful of what you ask.

17. If he could go anywhere in the world, where would he go and what would he do there?

18. How ready is he for a commitment?

19. Is there anything that he would give up if he fell in love with a woman who hated it?

20. How close is he with his family?

21. What are his lifelong goals for work, marriage, family, or a relationship?

So there you have it, some great questions to ask in the game 21 Questions which should help you get to know someone better, and even find out things like whether they are afraid of commitment or how compatible you both are. Have fun!

If you want to read similar articles to What To Ask a Guy in 21 Questions, we recommend you visit our Sentimental relationships category.

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What To Ask a Guy in 21 Questions