25 Questions to Ask a Guy to Get to Know him Deeper

During the early stages of the relationship, it’s normal to ask your guy some questions that will help you get to know him better. It’s also a good way to get him to talk to you, as communication plays a very significant role in strengthening relationships. Understanding what makes him happy and what pisses him off can also guide you in your actions and behavior towards him.

Some relationships don’t last because due to lack of communication. There are a lot of cases where people got married because they thought they found their one true love, only to realize after some time that they actually don’t know their spouse really well.

Here are some questions you can ask to get to know a guy deeper:

1. What do you think is your greatest achievement?

Any guy would love to talk about his biggest achievement as it can be seen as a form of success. Encourage him to share his story and make him feel more confident about himself.

2. What’s your family like?

You may or may not have met his family yet, but it would be nice to get to know his family and relatives, and the type of environment he grew up in. It’s always nice to hear stories about the people who raised him, the values he learned from them, and some memorable experiences that he had with his family when he was young.

3. What makes you happy?

Try to find out what makes him smile and what brightens his day. You may be one of the reasons behind that brilliant smile of his.  

4. What do you think about having children?

If you want to know if he wants to have children or not, this is a very good question to ask. His response will tell you if you are on the same page when it comes to building a family.

5. What are you scared of?

You’ll know that a guy trusts you when he’s not afraid to tell you his biggest fears. His answers may be as simple as his fear of heights or as deep as his fear of losing someone special.

6. What’s your best childhood memory?

Some guys don’t want to talk about their childhood memories, but if your guy starts talking, you have to pay attention. You’ll get to know what kind of childhood he had and it may help you understand him better.

7. If you could go back in time, what’s one thing you’d change?

Well, now it’s time to take a trip down memory lane and let your guy answer this question.           

8. What are your personal goals?

Let him share his goals and dreams with you. Let him know that you will always be there to support him no matter what.

9. How would you describe yourself in 3 words?

A guy who can describe himself in 3 words seems like he knows himself well. You’d also love to hear about how he describes himself.

10. What movie would you like to watch over and over?

This question will let you know the type of movie that he likes. You may also change this and ask about his favorite sports, books, hobbies or anything that you’d like to know about him.

11. Who’s your greatest role model?

It could be his parent, his older brother, a world leader, or an athlete. Knowing his role model will also let you know what kind of man he wants to be.

12. What’s one thing you’d want to change about yourself?

Nobody’s perfect and there’s bound to be something that a guy wants to change about himself. It can be a habit, a part of his body, or even his personality. Listen well and you’ll discover a lot about him.

13. What’s one thing you would not change about your life?

There are some things that we won’t ever change about our lives. Get your guy to talk about this and it will give you an idea about something that he really likes or something that he appreciates in life.

14. What’s the best advice you’ve ever received?

You can talk about the best advice that he has ever received from anyone. He might even share with you how this advice changed his life.

15. What’s your ideal job?

Your guy might have a nice job, but it doesn’t mean it’s his ideal job. Let him talk about his dream job.

16. What stresses you out?

Knowing what stresses a guy out can also help you think of ways to reduce his stress.

17. What’s the worst thing you’ve ever done?

He can give you silly answers, or share with you a deep, dark secret. Either way, don’t take it too seriously and just enjoy your conversation with him.

18. Where do you see yourself in 5 years?

A girl loves a guy who knows what he wants. And it’s even better if he’s working on reaching that dream. You can be there to support him as he chases his dreams.

19. What was the most embarrassing thing that’s ever happened to you?

You can have a good laugh together after hearing some embarrassing and awkward stories from him.

20. What things are you most passionate about?

A guy will definitely appreciate you taking an interest in the things that he’s passionate about. It doesn’t mean that you’d start playing basketball or start doing the same activities that he likes. It’s about showing him that you care about the things that matter to him. 

21. What’s one thing you’ve really wanted to do for a long time but haven’t done yet?

He might consider trying it with you. You can create some good memories and perhaps even discover a new hobby together.

22. What’s one regret you have?

Let him share with you his regrets and frustrations, and you’ll feel closer to him more than ever.

23. What is your strangest habit?

You can get some pretty funny answers. Not all conversations have to be serious.

24. What are you most insecure about?

Generally, people may feel hesitant to talk about their insecurities. If a guy doesn’t hesitate to answer this question, good for you. If he feels uncomfortable, let it go and just move on to the next topic.

25. What’s your philosophy in life?

This question may sound too serious, but you’ll know a lot about a guy based on his answer.

There you have it. These questions can help you dig deeper into a guy’s soul. Use them to make him communicate with you and create a stronger bond.

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