Good Questions To Ask a Guy

Good Questions to Ask a Guy

Looking for questions to ask a guy? Men are notoriously poor communicators in relationships. While it’s true that not all men suffer from this unfortunate state of being, the reality is that a majority of men have difficulties answering direct, personal questions that are not about something practical or external to them.

Guys are often on the defensive when questioned, sometimes worried about how they’ll be perceived and other times just unable to give what they feel is an acceptable answer.

Learning great questions to ask a guy is all about finding ways to get that boy that you’d love to know better to open up a bit and reveal things about him in a genuine conversation.

Men are always trying to impress other people with their answers, so the challenge is to ask questions that are thought-provoking and that inspire him to really think hard about how he feels. Getting to know a man is probably one of the hardest things for even the best women to do and can honestly take years.

A typical man is a bottomless pit of insecurity, contemplation and complexity of character. You’ll have to probe over years to get to the bottom of it, but if you think it’s worth it, keep reading to find out what questions to ask a guy if you really need to know what makes him tick.

Importance of Asking a Guy the Right Questions


Getting a guy to open up is all about asking the right questions. That can mean a number of different things, and there are several aspects to doing this correctly. Below I’ll review a couple of steps and things to watch out for when picking the right questions to ask your guy.

Make sure you follow them or you might end up offending him, putting him on the defensive, or making him more reluctant to give you honest answers in the future.

Start Shallow, and then get Deeper: Men hate being asked deep or highly personal questions out of nowhere. Men know that a lot of women are insecure about relationships and that women want to be reassured of where they stand in a relationship.

Men are different though! A man can go years without hearing “I love you” and he’ll still be convinced by the way you act that you feel exactly the same as the first time you said it. If you want your man to reassure you or talk about his feelings for you, asking him a big question right away can put him in defensive mode from the start.

You always want to start off with some lighter questions to set the mood for an intimate conversation. This has two effects. Firstly, you’re warming him up for more intense questions by getting him involved in a conversation.

If you’re already engaged in a conversation, he can more easily share his thoughts as you move on to more important or meaningful topics. Secondly, you’re showing him that you’re able to have a sensitive conversation without being judgmental or manipulative. This point is so important that it deserves its own section!

Listen without Judgment: Men are good at being honest when they’re not being judged. Sometimes they’re too good at being honest! When you ask a guy a question about himself, something that makes him vulnerable or puts him on the spot, it’s incredibly important not to make him feel like you’re judging him for his answer.

You may very well be judging him, but know that the end result, if he feels judged, will be the closure of lines of communication in your relationship. Men are defensive creatures.

They are naturally protective, both of themselves and of others. If a man thinks that you’re emotionally vulnerable to his honest answers to specific questions, he will almost definitely start lying about those things to avoid conflict.

As an example, imagine a man has a favourite personal hobby that you think is silly or a waste of time. If he tells you his hobby and you make him feel like an idiot, what he’s most likely to do afterward is hide from you the fact that he’s engaging in that hobby.

Do you want your man to go through his life with you ashamed about what he likes to do?

I know a woman who dates a younger man. Once she asked him if he ever thought about marriage – they are reaching an age where it’s more of a focus for her. Once he said no, she got upset with him until he ultimately agreed that he was thinking about it just to avoid the conflict.

He might have been happy with the relationship up to that point but hadn’t thought about marriage, not liked the idea for personal reasons, or had another issue, but because of that reaction, he actually changed his opinion because it caused a disruption in his normal life. This, I know, led to resentment in the relationship.

Listening without judgment means letting your man talk out his answers and address his feelings. You can ask questions but take care that you’re not really trying to convince him that he’s wrong or to see things from your point of view instead. Was the point ever to argue?

Empathize, Appreciate and Relate: These are three ways that you can encourage open communication between yourself and your boyfriend in the relationship.

Whenever you ask a question, try to consciously do two or three of the above, and your boyfriend will feel safer communicating with you about things that are personal or serious for him. Empathizing could just mean saying that you understand or that you see his point and validating his opinion on a topic or answer to a question.

This sends the message that you respect and value his opinion. Men also love to be appreciated. Let him know how grateful you are that you’re able to get honest answers from him, that he makes an effort to engage with you and that you can have interesting conversations.

Make him feel like you’re lucky to have the chance to get to know him. Finally, relating to him can be another way to make him feel more comfortable and validate his opinions. Explain how you agree or disagree but make sure to say that you understand where he’s coming from so it doesn’t feel like an argument.

Focus on where you see eye to eye and smile when you have something in common or when a question was answered just how you expected.

Strategy for Good Questions to Ask a Guy


Getting a guy to engage with you in 21 questions or another game about getting to know each other is sometimes easier said than done. Try to start the game in a quiet and safe place where you can spend a long time together uninterrupted.

Guys are more likely to feel vulnerable if you ask questions in a public place where others might overhear them. Remember, a lot of men are socialized to believe that revealing their emotions makes them weak and feminine.

While that belief shouldn’t be encouraged, we should still make sure that we acknowledge it and try to accommodate it. We can’t change a belief system by just abandoning it right away; it’s important that we engage with it and try to actually heal it.

You can change your boyfriend’s mind about how he should behave by interacting with him in a supportive and tactful way, but you should recognize what his starting point is for openness and communication and respect that at the same time.

Aside from that, try asking things in a way that give him a lot of options for how to respond. That way, he can decide his level of comfort when answering the question. You may also want to ask some either/or questions to make it more fun and give him some tough choices.

Take a question of marriage for example. Instead of asking “Do you ever see us getting married?” you could ask “At what age do you see yourself getting married?”

This is basically the same question but feels less threatening because you’re asking him to evaluate his own life trajectory, not your relationship. You’ll also be able to isolate whether his objections to something like marriage are personal issues (they most likely are) or issues related to your relationship.

Chances are that he loves you and wants to be with you, but may have difficulty forecasting commitment into the future.

Asking questions strategically means asking them in a non-threatening way, being tactful with how you treat the information you get and using them to create understanding between the two of you, not to polarize you or drive you apart.

The most important elements are making sure that he knows it is okay to answer questions honestly. Anytime you feel that your partner answered a question honestly, it’s because he was able to trust you and open himself up to you.

That fact alone, and not always his answer, should be evidence of the great bond you share in your relationship.

A Word of Caution for Questions to Ask a Guy


It’s always possible to get too personal when asking a guy questions. Try very hard not to push him to reveal something that he isn’t comfortable with, regardless of how curious you feel at the time.

Everybody has secrets that they don’t want to tell or stories that they may not feel comfortable repeating at that specific time. It’s important to be aware of this and not to force or pressure someone into telling you something they don’t want to share.

When you get upset or angry because somebody won’t tell you something that makes them feel weak or vulnerable, you’re really being a bully. More importantly, you’re being manipulative, and if your goal is to foster great communication then you’ve failed at it by becoming that.

It’s an easy line to cross though – you probably know that this person is protective of you and wouldn’t want to see you upset, so you’re really causing them distress with your behavior. Part of being an adult is learning to control your emotions.

You don’t throw tantrums anymore or scream and cry until somebody picks you up or brings you food, so why would it be appropriate to emotionally blackmail a friend or partner into giving up something they aren’t comfortable with?

Show how mature you are by being a positive communicator and respecting the boundaries that other people have. The greatest benefit of this is that once someone realizes that you can respect those boundaries and that you’re okay with hearing “no”, you’ve actually gained more of their trust and they’ll probably tell you what you wanted to know anyways!

List of the 20 Best Questions to Ask a Guy


Below is a list of some of the best questions to ask a guy that will promote great conversation, help you get to know him and help him open up to you in ways he may not have before.

This list obviously isn’t complete, but serves as a great starting point for getting a guy involved in more deep conversations about his personal life. You can bring up these questions during a game like 21 questions or casually when you are hanging out with him, even in an intimate setting.

These questions are great for pillow talk or for casual hang-outs. Feel free to make full use of the questions listed here and come up with your own ideas as well.

  1. Would you rather be smart and occasionally moody or blissfully ignorant and happy all the time? Do you think that empathy for others is a good thing, even if it causes you to suffer?
  2. If you could have one power or ability like a super-hero, what would it be? It can be anything from traditional powers like laser eyesight to something mundane like the ability to perfectly open a milk carton every time.
  3. Have you done anything that you regret? What is your biggest regret in life?
  4. Can you remember a time that you felt very guilty? Why did that happen and what did you learn from it?
  5. If money was no object, what would be your dream job? If you’re not sure, what parameters would it have? Would you have a lot of freedom or a lot of structure? Would you work in a team or by yourself? What would you want to achieve?
  6. What television show or event is so important that you would switch your schedule in order to watch it live? (You can offer to watch it with them because now you know how important it is to them).
  7. What’s your favourite hobby or extracurricular activity? How often do you do that thing? Do you wish you had more time for it?
  8. What is the nicest thing anyone has ever said about you? How did it make you feel?
  9. Do you have any superstitions or rituals that you follow or have followed on a regular basis? Do those things give tangible results for you or do you just do them because of superstition?
  10. If you had all the money and any job you wanted, where in the world would you choose to live? Would you choose for the food, the climate, or for another reason? How do you think your life would be different from how it is now?
  11. Describe your entire life in a five or seven word sentence.
  12. What was the last book you read? How did you end up choosing to read it? Did you like it and would you recommend it for someone else?
  13. What are your three biggest weaknesses or character flaws? How do you think you developed those attributes? Have you ever tried to change them?
  14. If your life was a movie, what genre would the movie be in? Would it be a drama, a comedy, or an action flick? Which actor would play you in the movie?
  15. If you could have a threesome with two celebrities, who would they be and why?
  16. If you could eat just one meal for the rest of your life, what would it be? Do you think you would love it or would you go crazy from how repetitive it would be?
  17. Are you more of an early bird or a night owl? What are your ideal working hours or studying hours? When are you most productive and at what times are you terrible at getting things done?
  18. What is your biggest fear? Have you faced that fear before or do you know why you developed it? How do you cope with it?
  19. If you had just a week left to live on earth, what would you do differently? How would you spend your last day?
  20. What is your funniest or most embarrassing childhood memory? How old were you when it happened and what do you remember about it?

Post your comments and leave feedback below… Thanks for reading Questions to Ask a Guy

Pin It on Pinterest

Share This Wisdom

Help others change their lives!