What if you knew what men secretly wanted but they could never tell you

It’s simpler than you think and I’m here to tell you how.

Questions To Ask a Guy – 10 Relationship Experts Share Fun, Interesting & Personal Questions To Get To Know Him

by Anita Gadhia-Smith – PsyD, LCSW-C, LICSW, Peter Jones – LMFT, Ed.D, MA-MFT, Rachel Orleck – PsyD, Larry Blackwell – LCSW, AADC, Rachel Elder – LMHC, MHP, Rebecca Lanier – LMFT, EdS, MEd, Tracy Kelly – LMFT, Heather Petitpas – MEd, LMHC, Charlene Benson – LPC, CSAT, CMAT, Michelle Henderson – MA, LMHC

Questions To Ask a Guy

“Good communication is as stimulating as black coffee and just as hard to sleep after.”

~ Anne Morrow Lindbergh

Anne Morrow Lindbergh Good Communication Quote
Rebecca Lanier

Two necessary ingredients of a healthy relationship are play and adventure. 

Humans have a core drive to seek adventure, novelty, and newness. With this need for adventure comes play, humor, and laughter. 

If you want to get to know your man better, ask him this question: “What makes you feel the most alive and the happiest?”

Discovering what activities, interests, places, and experiences make your man feel most alive and happy will give you a window into what lights up his soul. 

You’ll learn when and where he is most engaged in life, most present-focused, and most connected to himself. This question will also give you insight into his values, ethics, beliefs, and priorities.

If he is able to answer this question easily and thoughtfully, it’s likely an indicator that he is in tune with himself and knows what brings him happiness and fulfillment in life. 

Chances are he makes regular time for play, adventure, and fun and balances this with other aspects of his life. 

If he has difficulty answering this question or gives a blasé response, your antennas should go up. 

There could be several reasons for this vague response. 

  • Maybe he’s never been asked this question and doesn’t know how to respond, 
  • Maybe he doesn’t regularly have fun or engage in things that make him happy, 
  • Maybe he has little self-awareness or doesn’t participate in his own self-care, 
  • Maybe he’s embarrassed to share his answer with you, or 
  • Maybe he’s so consumed with work that play and adventure are not important aspects in his life. 

Regardless of his response, follow up by asking him to tell you more about the significance of his answers and why they are meaningful to him. 

You could also invite him to share a memory connected to his answer or describe how it connects to his childhood or background. 

The research on marital satisfaction tells us that fun, play, adventure, and humor are key elements to sustaining a happy, healthy long-term relationship. 

So, if there is a potential future with this man of yours, you’ll want to know what makes him feel most alive and happy and move towards creating a shared vision that will support and honor your love in the years to come. 

Rebecca Lanier, LMFT, EdS, MEd – www.rebeccalanierlmft.com

Peter Jones

You are asking your date to make a selection from their experiences and make a link to who they are now. 

It thus is an opportunity to self-define. 

Self definition is both a crucial indicator of maturity and a way to know what someone is committed to, thus are willing to be held accountable for in future behavior. 

There’s no mistaking that this question has an interview quality. 

Dating is a kind of interview and you should want know how they make sense of and make use of their experiences as raw material for learning and growth. 

This capacity will be at the center of handling difficult times together. 

The question is flexible because it doesn’t specify whether it’s a romantic relationship, although many or most people will hear it that way. 

Asking about relationship failures gives you an opportunity to see if they understand that failures are always co-constructions—we are always at least partly responsible for the fate of a relationship. 

It probes for reflectivity, and if they aren’t ready for it, it gives you an opportunity to see to what extent they can think on their feet. 

Some of course will fail or choke at the slight increase of pressure in such an interview style question, possibly because they are slow processors and or are feeling nervous on this occasion, and that slows them down. But slow processing is not about intelligence so you might not want to rule them out just on that basis. 

The question is also less demanding than “why did you your last relationship end,” which is putting too much belief in the idea that we can ever know what happened fully. 

Thus it can be a set-up. At least early on, you can benefit instead from asking for reflection on the value of failures to shape one’s way of being in the world.

Peter Jones, LMFT, Ed.D, MA-MFT – www.westhartfordholisticcounseling.com

Dr. Rachel Orleck

I don’t know about you, but I want to date a man that reads. 

Reading is so important, not just to know that he is literate. When evaluating for long-term potential you want to know that they have interests outside of video games, drinking beer, and work. As a woman in the modern age, it’s important to know that this guy can keep up with you and continue expanding his mind.

Long term relationships rely on couples being able to connect with each other and continue to learn from each other. 

Couples that have their own interests are able to share a passion with their partner that can keep the spark alive and ongoing connection.

The worst thing that could happen is that you become attracted to a man only to then realize that you aren’t able to continue to connect with him long term.

Ask this question early. 

Not only will you discover if he has a lifelong interest in learning, but you will also discover his interests. This will open up conversation to learn more about his passions. With one seemingly benign question, you can learn more about his personality, his friends, his family, and how he grew up.

You can then decide if your interests and lifestyles are compatible for the long haul, or if it’s best to have a great date and then let him go.

Rachel Orleck, PsyD – www.relationshipswithgrit.com

Larry Blackwell

When I was a young guy I was terrified to talk to women. I remember thinking, “I don’t know what to say.” I accidentally stumbled on the solution however which has actually served me even to this day as a therapist. The solution by the way works for both men and women. 

You see my fear stemmed from my belief that I needed “to know” what to say. 

That is, that I had to be ready to manage the conversation regardless of where it went. Well, that’s impossible because there can be as many variations of the conversation as there are people in the world, so what was I supposed to do? 

The answer actually is quit simple. You ask them about themselves.

If your just meeting a guy and want to break the ice, compliment him. It should be sincere but not creepy. “ I really like your shirt” or “I like your haircut.” etc. 

If he says thanks and turns away you have only made a polite comment without actually putting yourself out there. 

If on the other hand he is interested he will respond positively by turning toward you. Now that he is facing you, your thinking, “now what?” 

Don’t worry it’s not that hard. 

After introducing yourself just start asking him about himself. “What do you do?” is a great place to start. He knows it’s small talk but the fact that he is still standing there says he’s interested. 

Ask him open ended questions about himself. 

Open ended questions are questions that don’t have yes or no answers but questions that allow him to talk more and share more. For example don’t ask, “do you like your job” but “what do you like about your job?” 

If you are finding him interesting he will know it and your interest will subconsciously encourage him to share more. 

All of us like to be heard and when we receive someone’s undivided attention it validates us as human beings. If you’re feeling a connection then just go with it and let the conversation unfold. 

For example if he tells you he likes his job because he gets to be outside, you can simply say, “why do you like working outside?” 

Your simple questions if asked sincerely will encourage him to share more and more about himself. 

Now, ideally he will return the compliment and ask you about yourself. 

If you pay attention you will quickly become aware if he is sincerely listening to what you say or not (does he look distracted or is he totally focused on you). 

If he isn’t sincerely listening he might not be the guy for you, but if he is listening then relax and enjoy the conversation.

Larry Blackwell, LCSW, AADC – www.fightdepression.co

Rachel Elder

Exploring his job role can give you insight to a few areas of his identity and development. 

Asking this can help you see if he has aspirations, is driven, has goals, or has passion. It will also give you a look into what is motivating for him. 

If you’re looking for someone who is action oriented and motivated, explore the journey he took to get into his role as it can often reflect whether he is action oriented and motivated or not.

Rachel Elder, LMHC, MHP – www.rachel-elder.com

Laura Streyffeler

Ask about the people who are closest to him. His friends, family and past relationships? Ask him about his parent’s relationship? 

Watching the relationship (or lack thereof) between his parents, set the blueprint for what is “normal” in relationships. 

Yes, that perception can change and grow, but watching his parent’s relationship, or lack of relationship, is the foundation for what an intimate partner relationship looks like to him. Remember what is “normal” in many relationships, is not always healthy. 

Ask him about his friends. 

People are generally a reflection of the handful of people that they choose to spend the most time with. 

  • How does he talk to and about his friends? Are his friendships long term or does he just “hang with” whoever is around? 
  • Are his friend’s people who will be more likely to rise him up, or bring him down? Does he, and/or his friends, drink or use drugs? 
  • If so, how often, how much, and how comfortable will you be spending time in this environment…or will he want to “just go out with the guys” and this will all be time spent away from you? 
  • Does he want to be a “big fish in a little pond” or is he okay with being one of the crowd? Is he a loner? 
  • Does he like to spend large chunks of time by himself? Does he spend time with his friends in person or on-line playing video games or on social media? 
  • Does he need to post his life, or now yours, on social media? Are you okay with that? 
  • Have any, or most, of his friends been in trouble with the law? How do you feel about that?
  • How do his friends treat their girlfriends/wives? Do they speak kindly and respectfully toward and about them? Are they faithful? Did he ask or want to meet your friends? 
  • If he does, is he the same person in front of them as he is when you are alone? Does he say nice or “no-so-nice” things about them when you two are alone? 

This could be a reg flag for isolating you from your support system later. Pay attention… 

Most importantly, ask him about his past relationships. 

Remember that I said “ask”, not “grill” him about his past relationships. The best predictor of future behavior is past behavior. Does he speak kindly about his ex-girlfriends or does he refer to the as “crazy, ex-psycho bitches”. 

If it’s the latter, run! 

If/when the relationship ends, and he likely will not take any responsibility for what went wrong or why it didn’t work and he will describe you the same way, with those same words to his next girlfriend. 

This blog focus was on what to ask, but I need to add that the most important measure in getting to know who a person really is, is not only by the way he answers the questions that you ask, but in how he listens to you when you speak. 

Whether you are asking him questions, or most importantly, when you disagree with him or his opinion. 

  • What does he ask about you? 
  • Does he seem genuinely interested or just making conversation? 
  • Do you feel heard, respected and validated when you speak? 

Before you get to know him, know yourself, what you want and don’t want. 

In addition to asking him questions, share whatever you feel comfortable with about yourself and see how he responds. 

Pay attention to what he says and what he doesn’t say in response to the questions that you ask him, and the people who are around and important to him. 

Laura Streyffeler, PhD, LMHC, BCETS, CCDVC, CCFC – www.drlauracounseling.com

Tracy Kelly

This question explores what the man values, as well as what you can expect from him in a relationship. 

If his top priority is God or some type of spirituality, this will let you know how he approaches life. If one of his top three priorities is family, this is good to know if a family is what you want and something you value as well. 

Your top 3 priorities as well as his do not have to be exactly the same, but they should be aligned in how you focus your energy, behaviors, and intention. 

If he one of his top 3 is security and he focuses on saving every dollar he makes, and yours is not, this could create problems later on with how money is saved and spent as a couple and family.

Dr. Tracy S. Kelly, LMFT – www.DrTracyKelly.com

Anita Gadhia-Smith

Asking this question will tell you a lot about what he values in his life and what is important to him. Shared values are the most important ingredient in assessing a relationship and whether your relationship can evolve and move to a deeper level.

The type of priority that he has will also tell you what sort of person he is. 

If it is a superficial or external priority, like money, that tells you that he is focused on achievement, competition, and external success. He might be someone who is driven by needing to prove himself, which could reflect a deeper sense of insecurity. 

If he tells you that his highest priority is family, that is a different sort of person. This is not to say that money might not also be important to him, but his highest priority tells you the most about who he is. Someone who values family first, will probably be loyal and solid in a relationship.

Anita Gadhia-Smith, PsyD, LCSW-C, LICSW – www.drgadhiasmith.com

Heather Petitpas

This question, or some form of it, can be revealing to ask a new dating partner. 

Finding out what his intention is behind dating can help you see if there is compatibility right off the bat. 

Based on his answer you can learn a lot about where he is at in his journey. 

His answer may reveal if he is looking for something casual and fun-to meet someone to go out with, engage in intimacy and perhaps enjoy activities with. 

If you want to keep things simple as well and his answer aligns with what you want then you guys could be off to a great start. 

You may be compatible in other ways as well. 

If he replies that he is serious to find something long term then you are learning that he is ready for commitment and settling down. 

If this is where you are at then continuing to date him may feel like a green light-perhaps you two will be a good fit in other areas as well.

It makes sense to have fun in the beginning of dating-to keep things light. 

Yet it also makes sense to not waste your time-to date from a pool of people who want what you want right off the bat. 

Learning the answer to this question soon will help you set the expectations realistically as to what dating will look like with this person. 

You can then continue to learn more and have fun as you have an idea as to whether this will last one night, a few months or perhaps the rest of your life. 

Heather Petitpas, MEd, LMHC – www.tissuesfortheissues.com

Charlene Benson

First, his response tells me if he is adventurous. 

It also gives me a hint about how much freedom and encouragement he’s had growing up to think and imagine. Someone living in a very controlled environment doesn’t have an opportunity to develop creativity in that way. 

Having him tell you what he’d do provides insight into his most passionate interest. 

Maybe you’d like to join him on the adventure, or maybe that’s not something that would interest you at all.

Gaining understanding about his motivation gives you a peek into his character

It offers a clue about what drives him and his tendency to either think of himself first or others first. It also could spark further conversation about travel, activities you both like, and opens the door to deeper understanding of what makes both of you tic.

Charlene Benson, LPC, CSAT, CMAT – www.bensontherapist.com

Michelle Henderson

Asking this question tells you two things. 

First, it tells you if he is ambitious and motivated. 

Lots of people have goals but hearing what (if anything) he’s doing now to get there tells you how serious he is about working on himself and reaching the goals he is setting for himself. 

Second, it gives you a clue as to if your goals are similar. 

It could tell you what type of work he wants to do, where he wants to travel, or if he sees himself settling down anytime soon. Hopefully his goals intrigue you and turn you on (even if they’re different from yours) instead of leaving you confused and disinterested. 

And if he doesn’t have any goals? This could be an early sign that his life is stagnant and not going anywhere.

Michelle Henderson, MA, LMHC – www.nextchapter-counseling.com

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The TRUTH About Why Men Pull Away

If you want to trigger strong feelings of attraction and adoration in your man, you have to know how to get on the same frequency with him.

The key is understanding men on a deep emotional level, and how the subtle things you say to a man affect him much more than you might think.

If you’re frustrated with your man going cold, losing interest, or pulling away, then this video is a must watch.

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