Best Questions To Ask A Guy To Understand Him Better

There are so many ways to get a guy interested in you. However, it’s a vastly different prospect when you’re talking about trying to actually understand him, and that requires a deeper interrogation of his inner self. Obviously you don’t want it to seem like an FBI interrogation, but asking some pointed questions can let you know more about him and who he is deep down. Here are some of the best questions to ask a guy to understand him better and bring you closer together.

  1. Where do you see yourself in five years? If he’s an ambitious guy, he won’t be satisfied with where he is in life right now. He’ll always be striving for more, going after his goals and working to improve himself. With all being well, where does he see himself in five years’ time? This gives you insight into what matters to him and the plans he has for his life.
  2. What’s on your bucket list? We all have things we want to do someday when it’s possible. Whether it’s traveling, running a marathon, learning how to paint, whatever — there have to be things that he’d like to try, master, or accomplish in the coming years. What’s on his bucket list? What’s on yours? Discussing this can help you determine long-term compatibility and can be one of the best questions to ask a guy to get to know who he is deep down.
  3. How would your best friend describe you? You know how he’d describe himself because he’s likely told you that already, but how would his best friends describe him? Would they say he’s stubborn, loyal, hilarious? Encourage honesty here (and feel free to ask his friends one day to see if those descriptions match up).
  4. What’s the best thing about your life right now? Sure, he’s always striving for more, but there must be things about his life that he loves right now. What’s something that makes him happy or proud about where he is? This will tell you what he values and
  5. Which family member are you closest to? Is he super close to his mom because she raised him as a single parent? Is his brother his best friend? His sister? Finding out his relationship with his family is important, especially because if you end up together long-term, they’ll be your family too.
  6. What’s your idea of a perfect first date?  This is one of the best questions to ask a guy because it tells you what his views on dating and relationships are. Is he into super romantic dates like candlelit dinners or is he into something more action-packed like bowling or go-karting? This helps you understand what to expect from him in your relationship and also gives you some great ideas for future dates.
  7. What’s one thing you would change about your past if you could? Yes, everything happens for a reason, but there has to be something in his past that he wishes never happened or wishes that he could change. What is it? The answer to this question offers insight into his character in a way that other questions on this list can’t.
  8. Which of your five senses would you give up if you had to and why? No one wants to do without any of their senses, but if he had to give up one, which would it be? This is one of the best questions to ask a guy because it’s seemingly pretty fun but can actually tell you a lot. For instance, would he never give up his hearing because he loves music too much? Is he a foodie who can’t imagine living without his sense of taste?
  9. What’s the hardest thing you’ve ever done? The tough times we go through are the ones that truly shape who we are deep down. What’s the biggest challenge he’s ever faced and how did he overcome it? How did it make him feel once he was out the other side?
  10. When was the last time you cried and why? Guys aren’t known to cry very often, so chances are the last time he shed a tear, it was for a significant reason. Find out why and what was going on at the time. If you find out he cries a lot, you can pretty much bet on the fact that you have a sensitive guy on your hands.
  11. What do you do for fun? Ask him about what he likes to do in his spare time. It might, on the surface, sound like just small-talk, but there’s more to it than that. You learn things about him and you can attach an action to it. You can either research his favorite football team, watch matches together, or, you can build dates around it. This makes your relationship personal from the start by asking the right questions. You cut straight through the wasted time and get invited to watch him play basketball in his rec room. He will view you as part of his daily routine, not just a message to remember to reply to at the end of a long day.
  12. What’s your background? This is the time to drive through those smaller questions. It sets up how you talk to him, and how you view him in the context of his experiences. If you start out by asking him about his education, or the town he lived in, that’s a great passion point. You won’t run out of questions or things to say because these are big life events. You’ll both have memories for days to discuss. As well as this, it’s not an intimate question so you don’t have to worry about it not being appropriate or anything.
  13. What drives you? This is a slightly bigger question. It’s asking your crush to reflect on their life and times and think about what gets them out of bed in the morning. They might realize something about themselves that they didn’t know before. Or, something that they didn’t articulate before now. You will probably do the same in return. That’s important with relationships – you should grow together. Push each other.
  14. What’s your most treasured memory? This doesn’t necessarily have to be a positive memory. Or one that he really thinks about. But he will know what the answer is, in his gut. This is the value of engaging with that stage of asking each other questions. You know that this person is important to you, so you want to know as much as you can about them. It might be a painful memory or one that really defined the direction that their life took. But it’s a privilege to be in these kinds of conversations.
  15. What are your biggest, craziest dreams? Does he have something that drives him? Some career ambition or personal goal? That is something that can be so attractive. That sense of aspiration and ambition prove that he’s got something about him and wants to make something of himself. It also lets you know who he is at his core. For instance, he might be an accountant by day but wish that in another universe, he could have joined NASA and gone to space.
  16. What’s your worst mistake? This is a question to ask when you’ve maybe had a few drinks and it’s the wrong side of midnight on a Saturday in December. You can tell him yours so that it’s equal. You will feel a strong sense of intimacy during these moments.
  17. What are you looking for in life? This is one of the biggest questions that you can ask someone. Why not be bold and ask it early on in your relationship? You’ll understand how his mind works. That will help you meet his needs later on, and in turn, communicate that you need certain things too.
  18. What’s the best place you’ve ever traveled to? This is a great way of introducing some positive memories and nostalgia to the situation. Particularly, if you asked these questions chronologically… This will get them smiling and will give you travel inspiration. How can you lose?

Just ask whichever questions you are interested in hearing the answers to. Focus on what you would want to be asked, not just superficial nonsense. That’s how you get really productive, memorable conversation going to feel closer.

Hannah has a Masters degree in Romantic and Victorian literature in Scotland and spends her spare time writing anything from essays to short fiction about the life and times of the frogs in her local pond! She loves musical theatre, football, anything with potatoes, and remains a firm believer that most of the problems in this world can be solved by dancing around the kitchen to ABBA. You can find her on Instagram at @_hannahvic.
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