2285. Shyness Helps Uncover His Character

Her Highness Peach Blossoms, in a delightfully honest expression includes this, “I question why I can’t seem to go beyond the initial attraction with a couple of seemingly Mr. GoodEnoughs. Modesty, attractiveness, being restrained doesn’t seem to stir men to do more.”

Her Highness That Horse is Dead agrees, “It sounds like you and I are of a similar pattern. I’m introverted and shy and so I always thought that my efforts to show a man my interest (while maintaining modesty and restraint) were perceived loud and clear. What I’ve come to realize, however, is that my idea of “loud and clear” may be like an iceberg to a man ….”

In both cases, I conclude this. The guys grow bored because they aren’t challenged. Gals don’t ask questions, never put men on the defensive from which they can rise to the challenge and recover, apparently ‘win’, and thus add merit to their opinionated sense of great worth to the gals. Ask more questions and the guys will pay more attention and enjoy more encounters that are hopefully dates.

Gals should remember this, braggarts grow bored listening to themselves tell different gals the same stories. If gals ain’t unique, vaginas are all the same.

Neither gal mentioned above stresses her uniqueness and guys lose interest. Others have similar problems and I think I’ve finally identified a solution. You ladies keep too much to yourselves just when the occasion calls for the opposite. You let guys drag on and on about their accomplishments and promise of worthiness to you—aimed at getting you in bed of course—while you entertain yourself as being the object of each guy’s apparent attention and hopefully affection. Sorry, men don’t work like that.

Modern women use a weak strategy aimed at benefiting guys and causing disadvantage for ladies. I propose something else.

As a smart date you let the guy talk about himself, which is superbly wise, but you go too far. You are entitled in all dates to mention a few subjects to help you identify both his character and his worthiness to you for future dates. If you do as I advise below, he will also make a much faster and easier assessment of your worth to him and vice versa. What I propose below is designed to keep him on your side until you decide he is or isn’t Mr. Good Enough.

Women need a new strategy in order to put all men in their proper place in the hierarchy of the genders. All that men tell you is self-serving and—of necessity because of both masculine adolescence and women’s eagerness to believe—half of it is crap. I propose such a new strategy and hope to describe it simple enough to be easily adopted.

Major female interest. Any successful relationship requires, and every relationship expert is capable of putting her man off balance from time to time. That’s not when he’s most vulnerable because he may get honked off. But it’s when he’s more easily read for what and who he is and could possibly mean to her.

Purpose. With just a smidgen of determination, shy ladies can overcome hesitancy, enlarge their courage, and gain a wealth of knowledge about a man merely by asking specially designed questions. Doing so provides a better eval of his worth to her; it enables her to indirectly expose character traits that remain purposely obscured or hidden when he does all the talking.

Method. She now and again asks specific questions that neither disturb the flow of conversations nor upset his apple cart. She patiently and pleasantly just inquires about his past, personality, habits, and opinions. She challenges him to describe himself in ways that inform her rather than keep himself focused on what he thinks are impressive about himself.

Pay attention, ladies. Your challenges to him make you unique. Oh, he may not like you for it, but you need to be unique from other women for his thoughts to ever turn toward marriage.

Questions you may ask. (Numbered for easy reference.)

  1. So far in life, what’s your greatest achievement? What are you proudest of?
  2. So far, what’s your biggest mistake? What are you least proud of?
  3. Where did you get your work ethic? (If he doesn’t understand the term, he doesn’t understand the role of work in his life, so dump him soon.)
  4. How did you earn spending money in your teens?
  5. How did you work your way through college?
  6. Are you still in touch with your teen/college friends? Do you assemble regularly? Would you like to?
  7. Have you ever had a girl as best friend? From kindergarten to college. No love or anything, just a friend? What made her so valuable to you?
  8. How would your family have responded if you had gotten a girl in trouble in high school?
  9. Were you able to save money in your teens? Buy your own car?
  10. What roles do you inherit as a survivor if your parents die suddenly? Siblings? Estate settlement? Inheritance?
  11. If you could have any car in the world, which would you choose? Why?
  12. If you could live anywhere in the world, where and why?
  13. Ever consider entering politics? If so, where would you aim your main effort?
  14. Who do you love most? Your mom or dad? Why?
  15. Nothing personal and I just mean in an academic sense, but who taught you how to love someone?
  16. No details please, but if you have been dumped, whose fault was it? Not why, just who?
  17. Did your grannie play a part in your upbringing? Influence you much?
  18. What or who has influenced you the most in life?
  19. If you were God, what would you fix?
  20. Do you live up to something or someone bigger than yourself?
  21. What do you think is the most important or dynamic trait of a gentleman?
  22. If all men were gentlemen, what would women be like?
  23. If all women were ladies, what would men be like?
  24. What and why were your best and worst subjects (not teachers) in school?
  25. Who and why were your best teachers in school?
  26. What’s the most vital ingredient to raise a good child.
  27. Do you agree or disagree? Children should be raised to be good adults more than to be good children.
  28. If you had to do school over again, how would you do differently.
  29. Imagine yourself as a military man; how would you feel?
  30. Would you rather be a cop or a soldier?
  31. Thinking of the military, what service would you most likely join?
  32. Would you rather be a father or grandfather?
  33. If you were very rich, how would you point your life? In what direction?
  34. What is more important? How much money you have or how much control you have over it?
  35. When and how are you the most valuable to yourself?
  36. What would you do if an ex ratted to friends that you lack sexual ability?
  37. Not how many you want or don’t want, but what’s the max number of kids you think you’re capable of raising? Not financially but emotionally.
  38. While growing up, do you think you learned how to father children?
  39. While growing up, did you observe by example or have a role model for how to husband a wife?
  40. What does loving someone mean to you?
  41. How do you handle yourself when you have to deal with people who appear to be much smarter than you? How about dumber?
  42. How much crap are you willing to take from a boss? At what point does your integrity refuse to take more?
  43. If you married, what would you consider normal if your wife cheated on you?
  44. If you married, what would you consider normal if you cheated on your wife?
  45. Whose your favorite hero or role model in life?

And you ladies invariably respond with this. “But I could never say such things.”

And I say, then find some other questions that you can ask. Your relationship success from time to time will depend on your ability to put him—apparently very innocently—on the defensive and enabling him to talk his way away from whatever made you want to change the subject.

You don’t have to use all 45 of those questions to uncover the character of a man of interest. But you need to use some or others of your own choosing. Without your uncovering his character to your examination, three shortcomings arrive unhindered into every relationship: a) You won’t be unique enough for his learning to respect and like you enough for deep love to develop. b) You won’t truly know the man you marry. c) You will find marital misery long before marital happiness.

Attention, ladies. I know you will strongly object and eagerly withdraw from what I just wrote. It’s too big a change for anyone to adopt out of the black and white of so much info. Accept the spirit and test out parts of it for yourself. See if you don’t get more affirmation from guys than previously. I write from the ideal, you need to convert it to whatever is practical for you and you alone.


Filed under courtship, Dear daughter, feminine, sex differences

16 responses to “2285. Shyness Helps Uncover His Character

  1. That Horse Is Dead

    Sir Guy,

    I must say the thought of sitting across from man of interest and asking, “What would you do if an ex ratted to friends that you lack sexual ability?” causes my face to flush just thinking about it:) Maybe you could create a “Is He Mr. GoodEnough?” iphone app that we can pull out while on dates with pre-loaded questions! I would definitely download it. There was an interesting article that ran in the NYTimes, “To Fall in Love with Anyone Do This” back in February 2015. It reports about an experiment done to see if two complete strangers could fall in love with each other by answering a series of progressively intimate questions. A little different than what you are saying here, but I think it is worth a read.

    Your Highness That Horse Is Dead,

    I chuckle at your flushed face; you won my heart.

    Now, let me counter with this. You date a guy of interest. All he wants to do is impress you that he may well be the greatest lover of all time, but without ever being direct about it. He wants you to conclude without his risking overstating and offending you.

    You want to keep him awhile but not unless he changes his attitude. And so you very innocently and indirectly squeeze this into the convo. “Did your ex really mean what she said to so and so? Something about your describing what you can’t produce. Not sure what she meant, but does that reputation bother you?”

    He will change the subject and his attitude, and you’re back in control of the convo. So, don’t arbitrarily set yourself against anything; you may find a need for it when least expected.

    I regret total inability to even begin to make an iphone app. Can’t imagine how it could be used much less made worth the effort. You see, I don’t believe in rules. I believe in you having unique knowledge out of which you select what’s serves your best purpose in each situation.


  2. My Husband's Wife

    Dear Sir Guy,

    Just getting back into the WWNH loop and was sorry to hear that you’ve been experiencing back issues. I wish you well and hope that you’re on the mend as I understand that sort of pain to be excruciatingly painful…and stubborn! From my end, it looks like you’re still firing on all cylinders despite the pain as the articles have been fantastic —especially this one. WOW!

    This article is so in important on “HOW” to date to find out the character of a man. I believe you could also say it’s “finding out what makes a man tick” or “peeling back the layers of the onion to see what’s inside.” This way of questioning puts the woman in the position where she’s the buyer and in charge of the relationship (as the expert). She’s evaluating whether this man is worth her time and effort moving forward. She’s assessing red flags and probing deeper to see if he has major character flaws that she can’t live with and therefore it’s in her hands whether to continue or put him back in the parade.

    I would also say from prior experience (success + failures dating) that when I was able to dive into these sort of questions you cite uncovering character (probing deeper into personality) I was always asked out…and then asked out again when I continued to do so on the date. I would always be the one to end it if he didn’t measure up. When I was unable to do this (too “in love” / nervous that I couldn’t effectively lead the conversation in this manner) the dates always flopped and no call back…if I ever even got the date. I can recall those dates where I was only able to speak of superficial things such as the weather and classes and current events. BORING!!!!!!

    My husband would also affirm that he likes it when someone does this sort of probing/challenging of his personality. He’s told me before that he appreciated the fact I wanted to find out and know what made him tick.

    I also thought it interesting that you noted that men get tired of bragging about themselves. I can see that these sort of questions would be welcome as they pose an interesting challenge to them—to go into a deeper emotional range is something that needs to be effectively drawn out. I also believe this is a great way to build an emotional connection between people without sex involved. And he sees the woman who has this real sort of interest in him—what’s inside—as well, fascinating.

    To me, this sort of questioning is also just a part of naturally being interested in a fellow human being, whether male or female. It’s always interesting to find out about others, what motivates them, why they believe and do things they do, what was their past like, etc.

    Sir Guy—thank you for connecting the dots here. I believe it will truly help many women figure the way to show interest. I had never thought of it this way before so my eyes have been opened. Truly something women have never heard before.

    Your Highness My Husband’s Wife,
    Your understanding far exceeds my hopes of trying for clear writing. Thank you.

    • Jen

      “To me, this sort of questioning is also just a part of naturally being interested in a fellow human being, whether male or female. It’s always interesting to find out about others, what motivates them, why they believe and do things they do, what was their past like, etc.”

      I could not agree more! Though bashful by nature and even stressed by social situations, what makes people tick has always intrigued me. I asked many of these very questions (though the ex ratting one…no…eep! Though I can see where it might occasionally come in handy) to many dates until I found my own Mr. Goodenough. It just seems so normal to do so. Isn’t getting to know someone in order to determine their worthiness the point of dating? (It seems to me that, really, many of these questions are just good to have ‘in pocket’ for social interactions if one is quite shy.)

      Alas, I know of one woman who jumped into a marriage without even, it seems, considering any of these things and she and her *entire family* are now paying the very heavy price. Very sad.

      Finally, I too have been out of the loop and was sorry to see you’ve been ill, but am glad you’re on the mend, Sir Guy. Hope the recovery continues!

      Your Highness Jen,
      I’m 80-90% recovered but it continues to affect my work schedule, just a little, tho.

    • Peach Blossoms

      Sir Guy,
      I’ve been wondering – is it usually safe to assume that if a man doesn’t ask that many questions in turn, that he’s not interested in the woman? Or is this kind of quizzing more of a feminine way to communicate? I read somewhere else that men aren’t inclined to prompt each other with questions when they talk. I thought that was quite an interesting observation.

      Your Highness Peach Blossoms,
      In general, yes to all three questions.

  3. Krysie869

    Best post yet! I believe I have this problem!! Thanks for being part of the solution!

  4. kapri20

    Excellent post! I too tend to end up in attentive listening mode even though I am not shy at all! I am going to practise.

  5. Peach Blossoms

    Sir Guy,
    Thank you for the advice and for making me laugh! 🙂
    This MGE and I texted quite a lot in the beginning and I asked him some questions that made him remark on how I seemed to like asking tough questions over texting. But I pulled back from texting because that’s *all* we were doing and I was actually a little confused about why we were talking in that manner (asking probing questions) if it wasn’t going anywhere (from what I could tell). Or maybe I was/am naive. He followed suit and well, we haven’t had much contact after that.
    Anyway, this will be my “homework” for now!

    Your Highness Peach Blossoms,

    Drop him these words in a text and see what happens:

    “I made a mistake. I interpreted your texting as lack of character that I seek in a man. I should have told you instead of just keeping it to myself. No response required.”


  6. Miss Gina

    I love this, Sir Guy!

    Lady MHW has said just about everything I wanted to say in praise of this article. It’s a gem!

    However, I would just echo the idea that men *like*–no, men need– a challenge, in every area of life…at least the type of man worth having. If she is not a challenge, she isn’t a prize!

    Having once been the queen of wallflowers, this fact would have struck terror into my heart years ago. Now that I’m older, though, I realize that a sweet, quiet girl who isn’t afraid to put a man on the spot in conversation is VERY intriguing to a man. “How can she be both?” he thinks. She becomes a puzzle he wants to figure out. Men love puzzles!

    Your suggestion of asking questions ingeniously puts a lady in control of the situation without requiring too much personality change if she is on the shy side. Pretty soon the guy will figure out that she is screening him, and it triggers either the need to measure up or the need to get lost.

    Also, she is requiring something in return for her attention. As you mention often, men value what they earn….great strategy.

    Your Highness Miss Gina,
    Much wisdom, sweetheart. Keep it flowing in this direction.

    • SouthernBelle

      Sir Guy,
      I understand “men value what they earn” as it relates to tangibles…job promotions, trophies for sports achievements, applause for building things, etc. but I don’t understand what a man considers “investment” when he’s dating other than spending money (tangible) on her. Could you please provide some examples of less obvious things a man considers investment that I may be overlooking and not giving him credit for.

      Your Highness SouthernBelle,

      That pretty lady Curlyblondy saved me. Just below she cites these that she remembered were posted in #252. Ain’t she sweet? I thank and quote her for saving me the research time.

      “Men appreciate what they pay for, and the more dearly they pay, the greater their appreciation. Pay, that is, with their interest, focus, time, manners, sacrifice, energy, laughter, fun, games, promises, mistakes, affection, commitment, politeness, devotion, and especially worry about losing her.”


      • curlyblondy

        “Men appreciate what they pay for, and the more dearly they pay, the greater their appreciation. Pay, that is, with their interest, focus, time, manners, sacrifice, energy, laughter, fun, games, promises, mistakes, affection, commitment, politeness, devotion, and especially worry about losing her.”

        a quote i remember reading, from post 252! 🙂

        Your Highness Curlyblondy,
        Thank you, darling, for doing the right thing at the right time. I love it when pretty women save me a lot of work.

  7. Peach Blossoms

    Dear Sir Guy,
    I just tried out the questioning spirit and had a quietly animated discussion with a man. I just wanted to share with you my happiness at being able to inaugurate this type of questioning as a topic of conversation naturally. I heard what he had to say about his personal belief system for the first time. Thank you for the ideas!

    Your Highness Peach Blossoms,
    You’re welcome. I love it when pretty women are pleased with themselves.

  8. Meow Meow

    Just reread these and it reminds me these are good questions to get to know any man better….be he dad, uncle, a kid, a friend, boyfriend/husband etc. Some of these I never even really asked my hubby! (And should have—would have prevented lots of miscommunication over the years!)

  9. Lady Penny

    Sir Guy and Ladies,

    I have two questions.

    The questions above are all stated as direct questions. My first question is, is it better to ask them that way or indirectly? For example:
    Me: So far in life, what is your greatest achievement?
    Me: I wonder what your greatest achievement in life is so far.

    Also, in what kinds of situations would a lady ask a man a question, directly and indirectly.

    Your Highness Lady Penny,

    It depends on what a gal is after. The context here is early encounters, dating, and early courtship.

    If you’re screening and need to apply a little pressure, use direct questions. Otherwise, indirect is usually the most respectable and inviting for a guy to speak up, to talk about himself.

    Direct questions put men on defense. Indirect ones tend to invite them to open up. Shy women do better with directness; it emboldens them. Outgoing women do better with indirect questions that kind of slow them down to listen.
    The context here is natural behavior. Directness challenges and invites competition. Most guys don’t appreciate it from women, including wives. Men won’t compete with their own woman; they fear losing and they can’t stand to lose to the weaker sex. Men presume they possess and should protect character strength, dominance, face, dignity, and other such traits that women lack but respect in men.


  10. Femme

    Dear Sir Guy (and Ladies),
    I went out with a few girlfriends recently and as I am the only one without a man at the moment the other women proceeded to give me advice as to what to do to snag one.
    They all agreed I didn’t need to work on my appearance (which I thought might be the problem) but I lacked “chatting skills”.
    At first I was apprehensive because even though 2 of the friends are married and 1 has a live in boyfriend, none of their relationships is necessarily what I would eventually want for myself, but then I gave their advice some thought, which brought me to this blog entry.
    I think it’s a BRILLIANT idea (if I can pull it off that is – but I intend to try). It does seem scary as it almost sounds like a job interview… but too much is at stake here to be shy I guess.
    My question is: what do we do with the data that we get by boldly asking the above questions.
    How do we glean a man’s character from the responses.
    For example, if a man was brought up without a father present, and consequently didn’t have a good role model for fathering and husbanding, does it automatically disqualify him?
    I’m thinking especially about my son’s generation – with the current divorce rate, many young men will fall into this category. My son included.
    What if a man didn’t have a good relationship with his father because the father is/was an alcoholic?
    What if a man has been closer to his mother than his father because the father was a workaholic and never had time for the son? He would have a good work ethic I guess but otherwise?
    Some questions also seem a bit obscure. Like the amount of money versus control of it and the father/grandfather question.
    I would be grateful if you could clarify this.
    I think an app would be great Sir Guy but in the meantime we can just print the questions out and read occasionally… Then they will hopefully pop in our heads when needed.

    Your Highness Femme,
    The questions are primarily to escape shyness, secondarily to keep a man talking about himself (it earns his respect). Third, screening determines his suitability for living with you and not the source of his unsuitability. Focus on him in the present and not on his past, which will be needed only if you intend to marry.

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