Interviewing Prince Charming

Guest Writer

Today’s guest is a special friend: David from The Blue Orchid of Texas. We visit each other’s blogs and enjoy interacting on Studio30 Plus. David always leaves wonderfully insightful and often funny comments here and I love our interactions elsewhere.

Anyone who has spent 60 seconds on David’s blog knows he loves women. But if you spend more time, you realize it’s not in an objectifying way, he simply worships women on all levels. David is a kind, thoughtful, bright man who has a way with words. The advice David gives today on Naked Girl is excellent example. After you have read this piece, please visit his blog and follow him on Studio30 Plus.


Over the last few weeks I have sensed a real need to speak out about the complex and often challenging subject of relationships between men and women. While it’s true that the subject is vast and often shifting rapidly based on individual preferences between the sexes, I believe that there are in fact some foundational starting places that need to be talked about. Trust me, I’m a romantic at heart and truly love happy endings but at the same time I have found them to be rare. That’s not bitterness speaking but experience of seeing and often being in the shoes of failure to thrive in relationships. And I have seen one too many “train wrecks” occur with women friends who didn’t see the train on the tracks until it was too late to avoid. You know, it is often said that first impressions are everything and I believe that in a sense that is true but even more so, I believe that when we are brave enough to ask the “hard questions” and listen actively and deeply, then we have an opportunity to both avoid unproductive and unfulfilling relationships and hurting the feelings of others who may be making assumptions of us that will remain unmet. Personally, I’ve found that the best part of relationships are found in the discovery and in the journey with others and not in just painting a pretty picture of a sunset together that may never be seen.

Truly, we are each relational creatures and we thrive and grow best when we are in relationships with other human beings. Yes, we are entirely capable of living alone and being single but I believe that our nature is best realized when it is engaged in dancing with the heart of another person. That said, how do we ensure that we are matching ourselves well with others who should share our heart’s desires? Is it having the ultimate profile on Perhaps, but what if we were able to seize the opportunity to ask the right questions before the relationship even began? One of the things that have suffered in the world of relationships between men and women over the last few years is that as a culture, we seem to have lost a practical understanding of what dating is really about. Dating has now morphed into a relentless pursuit for making it work with the one you just met and not a gentle and fun time of exploration of many potential loving relationships. That’s why we see so many people going from one long term relationship to another one instead of many people engaged in a fun dance of discovery to find the “right one” for them. We have also begun to overlook the importance of asking the right questions in the beginning of a relationship before it is too late. Why wouldn’t we want to know answers to our hearts questions? Are we afraid of conflict or losing interest in the guy who just asked us out? Seriously, wouldn’t it be far better to have one date that didn’t “go anywhere” than months of time and energy vested in something that ended badly for everyone?

This piece is written in honor of all women everywhere, whom I simply adore. It is my hope to provide you with some practical and nuanced questions, answers and guidance into the “real world” thinking of men and it is my deepest desire that you will use some, or all of it to take good and reasonable first steps in determining if the guy you just met will be someone who might be more than just a fun date. Is he someone who you need to let go of politely but quickly or could he be a man whose eyes seem to reflect the souls of your unborn babies?

Just keep in mind that these are merely suggestions or guide posts perhaps for you to use to craft your own insightful questions. I think the most important thing is to just ask some questions up front and not lose the moment in making assumptions. Certain surprises later may be “less than ideal”. For what it’s worth my sweet darlings:

Can I ask you some questions?”

Tell me what you think of kids and old folks“.

Are you serious? Why not start with “Do you want to have kids?” OK, here’s why I think that question – or some variation of it – matters very deeply; it matters because it goes straight to the heart of who this man is. Is he in the deepest place of his spirit, someone who truly cares about the weakest, the most vulnerable and often least valued of human persons? Because if he does value them then it’s probably a safe bet that he has a life-view that sees all people as unique human persons worthy of respect and honor instead of merely as people having little value or significance. And if it’s the latter then you may want to know that he probably on some level views those “little people” as objects. If you suspect that then your response should be, “Good luck and good bye dude.”

What would a fun date look like for you?”

 True he doesn’t know you yet and that is actually a good reason for you to ask this sort of question. You don’t want him telling you what you want to hear in any kind of manipulative way. You do want to see if he is creative, intuitive and adventurous to a degree that is comfortable for you. Let him show you his imagination and then see if it is a destination that you would like to visit with him.

 “Who are your heroes?”

 Right, it’s another heart question and really important. His choice of heroes or lack thereof will reveal much to you about what he considers to be of great value, honor and respect in life. Does he strive inside for higher and grander things? Would he have the heart’s motivation to defend you, protect you and guard you from forces and people that may harm you? From the core of his manhood, who does he look up to and respect? Who does he want to be like?

 “Tell me about something you find beautiful.”

This is a question that could reveal to you if he has a heart of virtue, creativity and the quiet space in his mind that can appreciate lovely things great and small. Is his view of the beautiful things in life shallow and surface or is there depth there and a nuanced view of life’s treasures? Does he see beyond the surface and into the depths of things? If he sees beauty in many things in life, then he is very likely to cherish you on days even when you may not be at your best. You want your man to see you as the intricate and delightful work of art that you are.

What are some things that make you happy?”

Here’s another question to peel back the layers of a man and see what he loves and appreciates. Is he complex and mysterious but still happy with simple pleasures in life? Or does he require more stimulation than you do to have fun? What you want to avoid is someone who not only challenges you but could end up either wearing you out or wearing you thin because he’s really a dud. It’s a subjective question, true, but we are looking at compatibility for the two of you. Even if what makes him happy is different from you, does he still have the certain spark of life that you are looking for?

Do you have any best friends?” and / or “Are you close with your family?”

I heard it once said that the most mature of persons are those who no longer believe that life is a play in which they are the main actor but see themselves as just delighting in being a part of it all; as encouragers, servant leaders and friends to many. Is he comfortable enough as a person to be free in giving himself away in friendship and in the sometimes challenging and frustrating world of family relationships? If he has no friends, nor any real family relationships, then what leads you to believe that his relationship with you will be open, honest and engaging?

What’s the funniest thing that’s ever happened to you on a date?”

Several parts to this question come into play; first, is he able to be humble and reveal awkward things with a sense of humor? Is he mature and balanced in his ability to place himself properly in the sometimes silly moments of living? Secondly, does he take himself so seriously that he can’t even see the crazy and absurdness of some situations? Finally, does he have enough confidence and experience with women to be gentle and lighthearted about dating?

A man falls in love through his eyes, a woman through her ears.”

Woodrow Wyatt






3 responses to “Interviewing Prince Charming”

  1. I SO needed to read this today. Thank you, David!

    1. Naked Girl in a Dress

      Isn’t it a great piece Kimberly? It’s a great starting point when getting to know someone new. Had I asked these questions early on with some of the guys I have dated, it would not have progressed. Learning the answers after your heart is committed isn’t the right order.

      Good luck to you with dating!

  2. Ok, I have to play devil’s advocate here. I think all of this is sound advice, for the most part, but I feel as though the tone suggests this sort of “search for the man who will take care of me/worship me/see no wrong in me.” I don’t see anything about equality here.
    “Would he have the heart’s motivation to defend you, protect you and guard you from forces and people that may harm you?”
    That’s what weapons and kick-boxing are for.

    “You want your man to see you as the intricate and delightful work of art that you are.”
    No. I want my man to see me as the delightful partner and human that I am. I am not a work of art any more or less than he is.

    “What you want to avoid is someone who not only challenges you but could end up either wearing you out or wearing you thin because he’s really a dud.”
    I agree with the wearing thin part. But… CHALLENGE ME. WEAR ME OUT. Make me want to strive for better, push harder, try things I’d never done before, or maybe been too scared to. You want the potential to introduce each other to new things, not just sit comfortably in the like-minded parameters of your lives. There needs to be newness and adventures. You have to challenge each other in order to grow.

    Don’t get me wrong. I LOVE the idea of asking questions in a way that helps you get to know one another. But I think that what you’re suggesting we ferret out of the answers is a little bit on the “put us on a pedestal” side. And I know you don’t objectify, and that’s not what I’m feeling here. I feel it more in a shiny night/distressed damsel sort of way. And I don’t think that’s realistic. I don’t want someone to come along and treat me like a flower. My relationship is amazing because he DOESN’T do that. We are friends, partners, lovers, caretakers…all on equal footing.