What Deep Questions To Ask A Guy

You’re probably wondering, “Why should I bother to ask deep questions?”

The reason is simple: they’ll help you get to know him better.

After all, it’s easy to get caught up in the everyday chatter of life or only see what others want you to see. But when you ask deep questions and listen attentively, it can make a huge difference in how well you know someone and even how long your relationship lasts! So if you want something more than just small talk and surface-level conversations, then read on for some tips on how to have great discussions with your guy.

How To Ask Deep Questions That Will Keep Him Interested In Talking To You And/Or Dating You

What do you most look for in a partner?

The answer to this question will tell you whether or not he’s looking for a serious relationship and/or if he’s had his heart broken before. If he says that there’s nothing significant about the person, then you know that he just wants to hook up with whoever is available, which isn’t necessarily a bad thing. On the other hand, if he says that there are qualities or traits that are important to him in a partner (i.e., someone who is kind, loving), then it could mean that this guy is looking for something more than just sex right now—and maybe even marriage!

If your date mentions any deal breakers when it comes to partners (i.e., “They must be funny,” “They must be smart”), then it might give you insight into what they’re looking for in potential mates as well as how they feel about these characteristics themselves. This could help you determine whether or not pursuing things further would even make sense at this point (because maybe their vision of themselves doesn’t match up with who they actually are).

What’s the one thing about yourself you would like to change?

What’s the one thing about yourself you would like to change?

Asking this question allows the person to reveal something they might not be comfortable saying otherwise. Perhaps they want more friends or a better job, or maybe they’re unhappy with some aspect of their appearance. Whatever it is, it’s likely that by listening to your friend explain why he feels that way, you can offer helpful suggestions as to how he could make those changes happen. For example:

  • I’m tired all day every day and don’t have enough energy for my kids!
  • Our children are only one and four years old—how do I find the time?
  • Do with what you have! You may need help from others (like me) but focus on quality time with them instead of quantity time. Maybe hire a babysitter once a week so both parents can get some alone time together too…

What was the best phase in your life?

If the guy you’re talking to is like most people, he will have had a few phases in his life that were particularly good or bad. Ask him what the best phase was and why. The worst phase? Why was that? What would he do differently if given another chance? If you could change one thing about your life, what would it be? What do you hope your life will look like in 10 years?

What was the worst phase in your life?

You may have heard the phrase “hindsight is 20/20,” which means that people tend to be more objective and wise about past events after they’ve happened. That’s because it’s easy to see things in a new light when you’re looking at them from the perspective of someone who is older and wiser.

So, if a man has had some tough times in his life, maybe he’ll have some important insights for you as well. Maybe he’ll tell you something like:

“The worst phase in my life was when I didn’t know what I wanted out of my career. It took me years to figure it out and now that I do know what I want, it’s much easier to achieve.”


“The worst phase for me was when my wife left our marriage because she said she couldn’t stand being around someone who didn’t love their job anymore.”

If you were given three wishes, what would they be?

What would you wish for? If you could have three wishes, what would they be? They can be grandiose or small. Like wishing for world peace or a million dollars, or maybe something as simple as meeting your soulmate.

If you had the power to change the world in any way, how would you use it? What do you feel most grateful for in your life?

What is your favorite animal, and why?

This is a great question to ask a guy because it will give you an idea of his sense of humor and personality. When he answers the question, listen carefully for the way he describes his favorite animal. If he chooses something common like a dog or cat, then it’s likely he has been asked this question before and knows how to answer it concisely. A man who chooses something exotic or unusual may be someone with more depth who can tell you what makes him different from other people.

Why did my boyfriend choose “the platypus”? His response was: “I have always liked animals that are kind of strange and unique in their own way.” This led into a discussion about why we love each other so much—because we both appreciate things that make us stand out from the crowd! I think this question would also come in handy if you want to know what kind of pet your date might want (no matter how goofy).

Are there any causes that you strongly believe in?

Are there any causes that you strongly believe in?

  • What is the cause, and what does it do for people?
  • How would you like to see them handle the problem?
  • Is your approach realistic and effective, or are you just saying “I want to help” without a plan of how to go about doing that?
  • What are YOU willing to do in order to make this happen (i.e., donate money or time)

How do you want to be remembered by others?

“How do you want to be remembered by others?”

This question is a great way to get to know someone, and it can help you understand their values and beliefs. You should ask this question if you’re curious about the type of legacy someone wants to leave behind, or if you have been trying to figure out what your own legacy might look like. It’s also useful for finding out how much thought someone has put into what life means beyond just living it day-to-day.

Get To Know Him Deeply

These are the deep questions to ask a guy to get to know him deeply. If you want to know how he thinks and feels about his past, or what his goals are for the future, these deep questions will help you understand him better than ever before.

You can also use these for deeper insight into yourself and your own life as well!


In conclusion, I hope this article has been helpful for you. If so, please share it with your friends and family.

Thank you for reading.

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