Be Bold! Dating Advice For Insecure Young Men

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“What does she see in him?” Both men and women ask this question when they see a man of unremarkable appearance with a strikingly attractive woman. Sometimes the quality is money, sometimes status, sometimes a good sense of humor.  Perhaps it is great charm, a good heart, or a rare temperamental match. The explanation can be found in a resemblance to a father or mother figure, as well. But what is often unseen is perhaps more important than any of these qualities: boldness.

A man who has confidence and acts boldly will find a companion, period. He may be a boor or a clod; he may be self-involved, dishonest, or have poor personal hygiene. Unfortunately, there will be some companionable soul who responds well to his strength, confidence, and persistence despite all these negatives. A young man should not let this person’s coarseness obscure the fact that such brutes still have something to teach him: prospective mates will admire your willingness to take the lead, to act, and to attack problems in a seemingly fearless display of self-assertion.

Scientists suggest that a tendency for women to be attracted to strong men is the evolutionary product of prehistoric life, when a woman needed a male’s protection and ability to carve out a living, especially when the female was pregnant or the children were small. That didn’t make such men “nice,” but it did make them essential. The good news in 2012 is that you needn’t and shouldn’t be some version of a caveman in order to find a way to a woman’s heart; and that women can do quite well without a man.

Even today, however, the boldest men are the types who keep knocking on a door until the door sunders under the assault; or display the cleverness to find another path to their goal when the door fails to give way. They can be admirable in their ingenuity, less so in their bullheadedness. Not every woman will appreciate those who behave as if they were cartoon caricatures of a “macho-man”, but a few will succumb to them. They might not be well-liked, but their relentlessness, their strength of will, their “not to be denied” single-mindedness doesn’t require a standing ovation. And that indifference to the admiration of others is by itself a quality that produces a quantity of admiration, at least from a few potential companions.

The take-away? Show some persistence. Expect some rejection. The strongest men aren’t impervious to the injury that comes from being set aside, but it doesn’t cause them to abandon hope. Some confident women will be won-over by a man’s constancy and pluck. Others will see it as obtuse — not “getting it” — or  stalker-like. Don’t be a stalker, but do show that you can take a punch without breaking down or running away.

Some men accept that they won’t win all the females they pursue, but take the regrettable attitude that “a woman is like a bus — if you don’t catch this one there will be another one along in 10 minutes.” Callous? Yes. Offensive? I think so. But — and this is the point — it is an approach to dating from which an insecure man can learn, while avoiding what is most reprehensible in these alpha males. To put it another way, don’t treat every lass as if your life would be incomplete without her after knowing her for only two weeks.

To succeed with women one needn’t be like the overconfident souls who are too full of their own self-importance and who too easily objectify women — the men who think that one female is easily replaced by another. Yet the shy, hesitant man should not assume that his many good qualities will be sufficient by themselves. Thoughtfulness, intelligence, the ability to make a good living, and perhaps even good looks can be insufficient without the addition of confidence, decisiveness, authority, and the capacity to take some chances. Lacking these, celibacy is more likely than celebration with a co-ed.

“Faint heart never won fair lady” or so the old saying tells us. A man must craft the hardiness required to take a blow, get up off the floor, and come back for more. His personal sensitivity and fragility can disadvantage him if taken too far, however good may be his heart. Cleverness and decency might not overcome a lack of will — of will power: the quality that makes one person a winner and another a loser, even though the loser might have better ideas and be a finer human being. A man who is too hesitant or expects the woman to make decisions for him risks not finding a mate, while the more decisive man will.

As I have written elsewhere, insecure young men need to ask themselves some questions: do you routinely efface yourself and place yourself at a disadvantage — letting others go first, speak first — reluctant to raise your hand? Do you hesitate to take your turn? Are you extremely self-sacrificing? Insecurity can make you wait and wait until the opportunity before you is behind you. Excessive deference displays little regard for yourself, even if some amount of it is often a sign of good breeding and consideration for others.

Of course, there isn’t (or should not be) shame in being an insecure young man. I dare say, most young men start out as insecure. But if you accept your position as a second-class citizen, shy away from challenges; let other, lesser males get to the front of the dating queue again and again, then at some point you have earned your loneliness. If you think that you must first make more money, get your degree, build your body, learn more about the social graces — all that is fine. Do learn what you can. But you still need the hard experience of actual contact with women; and you will probably have to practice a more assertive stance before you have perfected or achieved all the rest. The strength of your will grows with the use of your will, just as a muscle grows with proper exercise.

Take things (and women) on. Show initiative. Many of the fairer sex are waiting for a man to do this, not wishing to carry a relationship on their shoulders alone. They are probably scarier to you than reality justifies. More than a few lack certainty about what they want in a companion until a man offers a relationship-vision that is acceptable; persuades the female not by florid oratory, but by the radiation of personal strength and conviction.

There is a quality of robustness in this that needn’t and shouldn’t be abusive. Lead and there will be followers. Even better, show that you have strength and find a companion who matches you and with whom you can have a co-equal relationship. Look inside and find your ambition, your courage, your unconquerable determination to master your relationship fears and boost your confidence. Get therapy if that is what will assist you to become the person you wish to be — to get beyond awkwardness and social anxiety.

I am not suggesting that you be a brute. But you must be a man, young man.

For a few instructive personal examples of what I’m talking about that don’t have to do with the pursuit of women, see He Who Hesitates is (Sometimes) Lost.

The above photograph is a Be Bold Wikipedia coffee mug, taken on October 4, 2010 by LiAnna Davis and sourced from Wikimedia Commons.

He Who Hesitates is (Sometimes) Lost

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Fear and hesitation go hand in hand. They hold you back, creating a slow motion to your progress (see above) and sometimes no progress at all. The trick is to separate the two, to recognize that you needn’t wait until you are free of fear in order to act. Indeed, if that were the case, most of the people whom we consider brave would still be waiting for the moment of bold action that earned them the appellation “hero.”

Years ago I heard a panel discussion on the subject of Wagner’s opera cycle The Ring of the Nibelung that actually touched on the issue of courage and decisive action. The experts focused on the character Siegfried, who is described as someone who has never known an instant of fear in his life. Should we therefore consider Siegfried’s fearless behavior to be indicative of heroism and bravery? The panel in question concluded it did not. After all, they reasoned, how can one be a hero without fear to overcome? Only a fool would rush to action without being aware of the attendant dangers. But a brave and courageous man would know the perils facing him and choose to act in any case.

Most of us won’t face dragons or fire, of course, but we still will all have numerous chances to act decisively or to hold back. Here is a trivial, but instructive example from my own life. In college, I was fulfilling a PE requirement by taking fencing. Now, I wasn’t a very good fencer, despite being a reasonably good athlete. And, my heavy academic course load didn’t permit me the luxury of spending time outside of class to practice fencing. Thus, in the first seven matches I had against my classmates, I won only three, a pretty mediocre showing.

Nonetheless, I was competitive enough to want to win more often, so I reasoned that there just might be a way that wouldn’t take time away from my other studies. I realized that I was a relatively tentative fencer, and so I decided to become more aggressive. I set myself the task of getting in the first “touch” as soon as each new match began. The strategy worked. Of the next 17 matches, I won 14. I was almost always able to get a 1 to 0 lead within a few seconds of the start of the competition by catching my adversaries off-guard. Yet, despite my new found success, I was really no better at fencing than I’d been when my record was three wins and four losses. I was simply less hesitant, more aggressive.

I once had a biology professor named Hudson who conducted the “Quiz” portion of his classes in a way to encourage behavior similar to my fencing experience. You were graded on the number of questions you answered correctly and lost points if you answered the interrogatories wrong. Hudson asked the questions aloud and it was a race to get your hand up first and have him call on you to answer. Naturally, you had to make a quick decision as to whether you had the right answer. Very fast indeed. Those who hesitated were, as the saying goes, “lost.”

But how does this all apply to daily life, the life outside of the university. You might say that “normal” life is less competitive than my examples suggest, but is it? To answer that question, ask yourself how often you hesitate to do things, take chances, give public voice to concerns that might engender disapproval, avoid tasks that are difficult or challenging? Do you ask out the beautiful woman, or do you wait until you feel “ready,” only to watch someone else beat your time in getting her attention? Do you, at least sometimes, see a crisis as an opportunity? Or do you hold back, put things off, wait and hope that another or better time for action will come? Sometimes it will, but sometimes it won’t.

If your “default” strategy, your habitual tendency, is to wait, you have a similar problem to those whose standard operating procedure is to act impulsively, without thinking. It may be the case that “fools rush in where angels fear to tread,” but it is also true that you are an equal fool if you forever hold back, hesitate, and watch the moment pass or see someone else “seize the day (carpe diem).”

What I am talking about is fear and the uncertainty that fuels it. When we are fearful and decide not to take action, most of us feel an immediate sense of relief. That relief reinforces our hesitation, while simultaneously depriving us of the opportunity to succeed in the endeavor. Soon enough the relief will pass, but not the self-doubt and lack of personal esteem and confidence that might have been won by an effective action.

The danger in allowing too many chances to pass by is a life of “quiet desperation,” a life on the sidelines, watching others play the game, but not playing it ourselves. And, at the end of life, regret for the opportunities passed and the chances not taken is more likely to be troubling than the failed efforts made. Beware the heartache of the words “what if?” True, acting boldly often fails; but, it also sometimes succeeds.

No wonder, then, that musicians spend relatively little time passively listening to music. They are too busy making it.

Make music of your life, then. Let the trumpet announce (or remind) the world of your presence. Sing your song. And if you cannot, find a therapist who will give you the tools to beat back your fear and help encourage you.

The above image is an Animation of Newton’s Cradle created on August 8, 2006 by Demon Deluxe and sourced from Wikimedia Commons.