Getting the Answers You Crave: 30 Questions to Ask a Guy

Getting a productive answer out of a man is all about phrasing the question right. Do you know what questions to ask guys to get the answers you want?


Guys are not always deep thinkers. In fact, when it comes to most relationships, the fewer questions asked, the better. If you are not getting the answers that you want from your boyfriend, chances are good that he may not really understand what you’re asking. Having communication limitations, he may not even know himself what he is feeling or how to express it.

Instead of asking open-ended questions, phrasing your inquiries in the correct way may elicit the information you are looking for instead of leading to an argument or going around in circles without ever getting to what you want or need to hear. Below are the best ways to get some of the answers you crave. To box guys into thinking concretely, ask the following questions to force them into telling you how they feel. [Read: 14 awkward questions you should never ask a guy]

#1 Did I do something to upset you? Sometimes what you say and what he hears are two different things. Asking him point blank whether there was something you unwittingly said that made him upset will clear up any misunderstanding that you have about what you said or meant. [Read: How to apologize and say sorry to a lover]

#2 Are you ready for a long-term relationship? If he isn’t ready for a long-term relationship, then that really is something you need to know upfront. [Read: 8 genuine signs he wants a serious relationship with you]

#3 Am I making you uncomfortable? When a guy doesn’t know how he feels or what is being said, he will often feel “uncomfortable.” Pressing him further is only going to frustrate both of you even more.

#4 Do you feel successful at your job? If you want to know how work is going, try asking him about what successes he has had, not whether it is fulfilling to him or not.

#5 Why don’t you want me to come to family gatherings? If he never invites you to family get-togethers, don’t wrongly assume it’s because he doesn’t want you there. Instead of making assumptions, clearly communicate your concerns with him. [Read: 7 clear signs it’s the right time to meet the parents]

#6 Where do you see us in two months? Putting a definite timeline on things can keep your question from being overwhelming or too encompassing. The more specific you can be with your question, the more likely you will be to get a reasonable answer.

#7 What do you think I think of you? Sometimes the problem is not what he thinks of you, but rather what he thinks you think of him. Clearing up any insecurities that he has about himself will help him to open up and see himself the way you see him.

#8 What do you think I want from you? Getting your expectations for the relationship all out in the open is the best way to clear up any misunderstandings that may be coming between you. [Read: How to manage your expectations in a relationship]

#9 What did you just hear me say? Talking to a guy can be like playing operator. What you say and what he hears are rarely the same thing. If you say something and he doesn’t answer you, then ask him to repeat what you’d just said. You will probably be shocked at what he repeats back to you. [Read: Why do men hate talking on the phone?]

#10 What did I say that made you mad? If everything is going along fine in your conversation and then he suddenly withdraws, it’s important to find out what it was that you said to put him on the defense. Asking for something specific that upset him can help you get to the heart of the problem.

#11 Am I making you feel smothered? Sometimes we apply pressure without even meaning to. Often, the more you question him, the more he will retreat. Ask him if he just needs some time to cool off and regain his thoughts.

#12 Do you think I am on your side? This question will remind him that you are not enemies, but two people working together. [Read: How to build trust in a relationship and make it last]

#13 What do you think of me? This question will make him think of the positive things about you instead of the negative things that he may be ruminating over.

#14 Do you need some time to think before you answer? Women want answers… NOW. If you know that in time he will answer your questions, then it can be helpful to just walk away and wait for a time when he can answer you thoughtfully.

#15 Am I around too much? Give him the opportunity to be honest and tell you when he needs some space from you or the relationship. [Read: 10 obvious hints guys give when they want more space]

#16 Is there something I am preventing you from doing that you want to do? He may be harboring some resentment about something he intends to do that he assumes you won’t let him. Give him the opportunity to voice his needs and to clarify what he wants.

#17 Does having me around make your life better? Wording your question this way can help him to more clearly decide if having you in his life is mostly positive or mostly negative. [Read: 13 strong signs your relationship is built to last]

#18 What are the things that I do that annoy you? If you don’t address those things that may be irritating him now, they will only continue to grow and will turn from a molehill into a mountain.

#19 Is there something you need to hear from me? He may need to hear some specific words like “I love you” or “I want to be with you.” You may feel them in your heart, but sometimes they just don’t come out of your mouth. [Read: When should you say “I love you” for the first time?]

#20 Is there something you aren’t telling me? This question opens the door for honesty.

#21 Are you afraid of telling me the truth? He may not be telling you his feelings out of fear of reprisal. Give him the floor to say what he needs to say. [Read: How to stop lying to yourself and to your partner]

#22 Do you want to be with me? A straightforward and direct question, but it is one that he surely can’t dodge or shirk.

#23 What things do I do that you like? Not only will this make him consider what you do for him, but it will also tell you what you should keep doing to make him happy. [Read: How to make your man happy in 20 little ways]

#24 If you wanted to tell me something, do you think you could? It’s important to know whether or not he feels that he can be honest with you.

#25 Do you know how I feel about you? You love him, it’s obvious… to you. Make sure to look him in the eye and be truthful about your feelings for him. [Read: 25 ways to make your guy feel appreciated and cared for]

#26 Do you know what I want from our time together? He may think that you are looking to have kids, the white picket fence, and the vows exchanged, when all you really want is good sex, fun at the bars, and a Saturday night on the couch. This will allow him to clear up what he wants and what you want, too. [Read: 16 signs you’re not ready for a serious relationship]

#27 What would you change about me if you could? If it only took a little bit of change and effort on your part, wouldn’t it be worth knowing what he’d like from you?

#28 If I stopped asking you questions, how would our relationship progress? What he may not understand is that you aren’t asking him questions to annoy him, you are asking them because you simply don’t know the answers. [Read: 13 small changes that greatly improve your relationship]

#29 Do you see a future with me? This question will tell you whether you are a “fine for now” girl or a “future wife” girl.

#30 Do you think we are a good fit? Asking him this question will tell you whether or not he thinks you are the one for him, while also giving him enough wiggle room so as not to hurt your feelings.

[Read: 60 get to know you questions for a new romance]

If you are banging your head against the wall trying to get your guy to answer seemingly simple questions, you may not be phrasing them in a way that he can understand. The key is to ask nonthreatening and specific questions that will get you the answers that you need.

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Julie Keating

A writer isn’t born, but created out of experiences. No lack of subject matter, my life reads more like fiction than anything that could have been imagined...

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