Most Common Male Insecurities: Why You Shouldn’t Let Them Define You

Student: “Hey Rob, I’m 30 years old and I’m balding, do you think girls will think I’m too old?”

Rob: “You’re at your prime right now. You’ve got a great fashion sense, you’re in really good shape, and you have nicely trimmed stubble.”

Student: “Hey Rob, I’m in my mid-20s right now and my biggest anxiety is a girl wouldn’t want to have sex with me after we’ve kissed, I feel like she’ll run away after she’s seen how small my penis is.”

Rob: “If she kissed you already, has reciprocated your advances, and is comfortable with you, that is not likely, the size of your dong doesn’t matter, you’re putting too much unnecessary pressure on yourself for something that’s as natural as breathing, sex in real life is nothing like what you see on PornHub.”

Student: “Hey Rob, I didn’t get that promotion at work today, women will never want to go out with me because I’m not making that 6 figure salary that I was supposed to get after being promoted.

Rob: “When I was in college I was broke as hell and yet I was still dating pretty girls. I’m building a business right now and I can’t always afford to go out for dinner yet I’m still dating pretty girls. My point is your self-worth shouldn’t be attached to your bank account, if she cares about your income you’re probably courting the wrong person.”

No matter who you meet in life, there’s one truth that’s as true as the law of gravity: everyone has insecurities, it’s normal and it’s human. Some are better at managing it than others, and the ones who are better at managing insecurities are perceived as being self-confident.

It should come as no surprise that confidence is a big deal when it comes to success in dating. Confidence after all, is sexy. The problem is that confidence has been put on this pedestal as an unattainable thing or something that is as mythical as charisma, either you have it or you don’t.

I can assure you that like anything else, confidence can be learned and developed. It all boils down to understanding what you believe about yourself, breaking it down to the core, and actively challenging it. While it might not come easy, with enough work and consistency it can be honed and developed.

Even after years of working on myself, challenging my self-limiting beliefs, and overcoming a lot of those insecurities, I still have new ones pop up that constantly challenge me to keep going and improving. The only difference now is that I can be transparent and acknowledge it to myself and the world around me, be okay with it, and actively work through it. I don’t let it consume me, define me or my character, or stop me from pushing forward and growing.

After a few years of coaching and helping men and even women overcome their insecurities, I’ve come to realize that 90% of it is all mental, with only 10% being physical.

Confidence, especially how our modern age defines it, can be hard to come by. There is a whole industry built on confidence-boosting and quick fix solutions to the problem of not having any. If you don’t believe me go to your local newsstand, turn on the TV, or look at how businesses advertise their products online.

The advertising industry is built around tapping into some fundamental human need and insecurity and having that specific product pitched at overcoming that insecurity and being the solution to that specific problem. Don’t get me wrong, I’m not saying to be cynical and skeptical of every product that you see. What I’m saying is to just exercise a little common sense, critical thinking, and curiosity.

For example, If I hadn’t stumbled upon the ad on Google for Craft of Charisma or went to their Meetup lectures a few years ago, I wouldn’t be writing this article, and I’d still probably be consumed by my insecurities and never take proactive action towards improving myself or my situation in life.

After a few years of doing this, I’ve coached men from all walks of life, from your stereotypical tech nerd to someone you probably wouldn’t expect to have any issues in terms of self-confidence and dating… a Men’s Health cover model.

I can tell you that men are more sensitive than what our current culture gives them credit for. For all the perceptions about manliness and being macho, and how men don’t worry about the same things that women do, I’ve come to realize that the male ego is pretty fragile.

As men, we may be able to endure the ball-busting insults and friendly trash talking that is often part of male friendship, but there are certain areas that are just considered off-limits. They’re emotional generators of anxiety that wrecks a man’s self-esteem, causing him to spend hundreds if not thousands of dollars on sleazy products pitched as magic fixes. Case in point, the male enhancement pills you find behind the counter at your local convenience store.

Now, I’m going to list a few of the most common insecurities that men have, and offer constructive and seemingly common sense solutions on how to deal with and overcome them. As I’ve always said to you in the past, it’s my job to be brutally honest and straightforward. Don’t take anything personally and always remember to be objective with the advice I give.

Self-awareness is incredibly important if you’re trying to build your self-confidence. Take a good look at yourself in the mirror and acknowledge whatever you’re feeling insecure about. The first step to becoming confident is acknowledging whatever it is that’s holding you back, being okay with it, and taking ownership of it.

By taking ownership, I mean you should accept whatever it is you’re insecure about, and if it’s something that can be changed, then actively work on improving upon it.

Most Common Male Insecurities

Body & Physique

As a former fat kid, I can relate and empathize with men who have an insecurity regarding their body. With all the fitness magazines, advertisements of muscular men getting all the ladies, fat-shaming, unrealistic standards that Hollywood has instituted with their male leads, Instagram shots of guys with perfect abs and chiseled physiques with equally appealing female counterparts by their side, it can be an intoxicating feeling getting that validation of being ogled at by women.

The old adage that men are visual creatures whereas women are more emotionally and intellectually stimulated is not necessarily true. We’re all attracted to these traits, and women like the visuals too. If you don’t believe me, ask any girl how they feel about Magic Mike, or if you’ve got enough cojones, go to a male strip club and watch how the clientele reacts as the show starts.

As men, we’re always worried about being too fat, too skinny, too hairy, too short, too tall, not lean enough, not muscular enough, too vascular, not vascular enough… you get the point. Go to your local gym, pay close attention to the gym rats, meatheads, and guys spending so much time in front of the mirror to match that ideal. Women do it too, and it’s both irrational yet understandable, as we all want to be accepted, loved, and admired to a certain extent.

Dealing with Body Insecurities

I’m going to be brutally honest with you. For a very brief period in my life, I made extra money keeping my shirt off and wearing a bow tie during my former days as a bartender. Sure, it was fun at first being validated and objectified by the women. But over time it got pretty damn uncomfortable getting groped constantly, having to talk like a phone sex operator all the time, and having women lick shots of vodka off my young and hairless 20 year old abs.

It was nice being really lean and making money from that, but I was completely miserable just living off of chicken, broccoli, egg whites, and water. These days I prefer to just be fit and still be able to eat cheeseburgers and pizza. I’m not as shredded as I used to be, but I’m okay with that. There really wasn’t much of a difference anyway. Women still want to date me, and I’m pretty comfortable just being healthy.

Most guys think women, especially really pretty women, are only attracted to those super ripped guys, but in fact the opposite is true. Women’s physical standards aren’t really that unrealistically high. Sure it helps to be fit, but its not the be-all end-all.

I remember this time back in college when I was hanging out with one of my female friends. She’s really pretty and was part of one of the hottest sororities on campus. She told me that her ideal guy was someone who had the build of Tony Soprano and the same force of presence. At first I was surprised that she’d find big, chunky, hairy, and balding men to be attractive, but after taking a moment to think about it, it made sense.

I dug a little deeper into it and she told me that she was attracted to guys that reminded her of her father. If it wasn’t the physical traits, it was the personality that was the biggest selling point. This little tangent wasn’t meant to bash on fit people. The point is, you don’t have to go overboard and take t to the max unless that’s your career or you’re making a living off of it. Being in shape helps, but it’s not everything.

The most important takeaway here is that you should train to feel better. Exercise is a meditation and stress reliever in itself. Change your priorities and train yourself to be healthy and feel good. We’re all not going to have perfect chiseled physiques like the people you see on Men’s Health. But if you feel healthy, look healthy, and feel comfortable with yourself, that’s all that really matters.

Emotions are contagious. If you feel good about yourself, she’s going to feel the same way. Accept who you are, and don’t live up to some bullshit ideal to look or feel attractive. Everyone is built differently. Accepting your build for what it is while making an active effort to be “healthy” will do wonders for your self-esteem and confidence. Wear clothes that fit properly, groom yourself well, and most of all, don’t do it to look good, but rather to “feel” good!


For ages, men have tied their identity and self-worth as a “provider.” Their ability to care for and financially provide for their mate and family has been a measure of masculinity. As a result, men place an unnecessary amount of importance on their material and financial wealth. Go watch or listen to mainstream music where the bulk of the story revolves around the importance of material wealth.

Don’t get me wrong, that doesn’t mean I’m saying to drop everything in your life, give up all your worldly possessions, shave all the hair off your body, and embrace the lifestyle of a monk. At the same time, money isn’t the be-all end-all. I love money. I love the financial security it brings, the experiences it can buy, and the power it has to help my loved ones and the people around me. But you don’t have to be crazy rich to find love.

Dealing with Money Insecurities

Don’t tie your self-worth or self esteem to money. I view money as an extension of my happiness and as a result of the hard work and hours I’ve put into acquiring it. Take a look around you, we just recovered from one of the harshest economic crises since the Great Depression. We’re all trying to get by and live comfortably. Any woman worth going out with and dating would understand that.

If the girls you’re dealing with on a regular basis look at your bank account and not at your character or value as a person, you really ought to rethink what you’re looking for, quit dating shallow and materialistic women, and look for quality women that appreciate a man who has more going for him than just the size of his wallet.

Now don’t take the view that money isn’t everything and use it as an excuse to be lazy. If you’re struggling with your finances because you’re lazy, irresponsible, and have no dreams or ambitions, that’s an incredibly unattractive trait no matter how much you’re making.

Don’t use this as an excuse not to invest in yourself either. There are plenty of ways to look good in your clothes and groom yourself well on a budget. Research on Google and YouTube and spend your extra income on classes or some form of self-improvement. Whether it’s books, learning a new skill that’ll get you out of your financial rut, or a class like the ones we run to help you get out of your dating rut, remember to invest in your growth, not things that’ll mask your shortcomings.

Always remember that romance is more than material wealth. It’s about adventure, fun, spontaneity, and a positive attitude. I’ve gotten plenty of dates while being a broke college kid, and now as a broke entrepreneur working towards a dream and bringing a vision to life.

You can date without killing your wallet. I’ve had random and spontaneous dates ranging from a day at the beach, a spontaneous picnic in the park, running errands with a girl, sneaking into places, and cooking dinner with a girl at my place or at her place, followed by Netflix and a bottle of wine I “borrowed” from a Christmas party I went to.

Museums are amazing places for dates that are pretty low-cost and classy. You can also browse around on Eventbrite or Meetup to find fun events that range from free to just a few dollars if you live in a major metropolitan area.

My point is, don’t tie your confidence to your finances. As long as you’re working towards your dreams and ambitions, and working on yourself, any woman worth your time will be won over by your confidence, personality, care, wit, humor, and charm.

Penis Size

I guess if you had a top 10 list of male insecurities, this would be at the top. The size, width, and shape of a man’s penis is probably the number one source of male insecurity, and we’ve got commercials, ads, and male enhancement pills to prove it. Uncircumcised or circumcised, straight or curved, hairy or clean, every man has had the thought of how his manhood measures up and whether he’s normal or not.

Penis size has been associated with sexual desirability. A man who has a chode is just not a manly as a man who needs to put on magnums. If you’re not hung like a moose, you’re doomed to a lifetime of shame, laughter, and the butt of every single joke from women whom you’ve never even slept with in the first place.

Dealing with Penis Size Insecurities

I’m Asian, and for the longest time we’ve been associated with being effeminate and being very simple people with very small penises. But I still go on dates with pretty girls and have plenty of fun, and many of my former clients who are Asian have really attractive girlfriends. A wise man once said, it’s not about the size of the ship, it’s all about the motion of the ocean. If you’re insecure about the size of your penis, then try challenging that belief.

I read in an article somewhere to prove to one of my classes that penis size doesn’t matter that much. The average length is somewhere around five inches erected when measured from the base, and 1.5 inches in diameter. Bigger doesn’t automatically equal better. The longer your penis is, the more likely the odds are that you’re going to end up bumping your partner’s cervix, which is not fun for her.

If you feel like you don’t measure up, there are some things you can do to make it look bigger that don’t involve penis pumps or penis enlargement surgery. Losing weight will make you look bigger as the pads of fat around it shrink and pull back. Manscaping helps too. Just grab a trimmer or take it off, and it’ll make it stand out and look larger.

But the best thing you can do is accept what you’ve got, be happy that it works, and learn how to use it well. As I said before, it’s about the motion of the ocean. Many women out there aren’t much into hung studs. Men tend to think size is all that matters, but they lack the skill or finesse to make sex fun and pleasurable.

A man with a more modest penis is far more likely to figure out how to use it properly. Two hands, a can-do attitude, and a little bit of kinkiness will be in higher demand than a hung stud that’s got no skill or finesse and treats it like an industrial drill creating an artificial cave.

Male Pattern Baldness

I can’t speak for balding men or people who have lost their hair, as I was fortunately blessed with a thick mane (Thanks, Grandpa!) But if I did ever lose my hair, I would do one of two things: completely own my baldness and go with a Statham, or get a hair transplant.

A lot of men place such importance on having a full head of hair, maybe because they feel that balding is a sign that they’re long past their youth. In reality, male pattern baldness is incredibly common. If you think it’s a big deal, first go ask 100 women if they think it matters. A lot of them most likely won’t care.

Dealing with Baldness Insecurities

Remember what I said about getting a Statham? I was referring to Jason Statham. That guy is the epitome of manliness, and his partner Rosie Huntington-Whiteley is one of the most desired women to walk the face of this Earth. Bald is sexy.

The best thing you can do as a man is not hide it with a smelly toupee or a bad comb-over. Own that baldness and grow some stubble or a nicely-trimmed beard. You can’t fight genetics, but you can certainly fix and improve your lot. So forget about the Rogaine and the hair growth pills. If you can afford it, get a hair transplant.

Sexual Ability

Sex causes an absurd level of anxiety in men who’ve never done it. This anxiety can lead to performance issues, even in men who are more experienced in the bedroom. We’re forever worried about when we should expect sex or whether we’re pushing too hard or not enough for it. We think about and obsess over the amount of partners we’ve had, or how we compare to our lover’s exes and the amount of partners she’s had.

It gets even more insane and unrealistic when you throw porn into this already troublesome mix. Now we’re not just worried if we’re the best lover she’s ever, had but men are worried about stupid things like whether to aim for her face, the volume of their ejaculate, and once again… penis size.

Dealing with Sexual Ability Insecurities

Listen, nobody’s asking you to paint a Warhol with your love juice and your cock as the brush. If you can do that… well, you’re simply not human, and I don’t mean that as a good thing. First things first, STOP WATCHING PORN! It’s okay to indulge once in a while as a harmless vice like your occasional drink, cigarette, or blunt.

But my point is, porn is nothing like the real thing. It’s exaggerated, uncomfortable sustaining those ridiculous positions, and completely unrealistic. Basing your ideas and expectations on sex from porn is a bad mistake. Remember that every woman is different, with different tastes and kinks. Want to know how to make it fun for both of you and memorable for her? Just ask her what she likes, pay attention to her signals, and respond accordingly.

Sex is supposed to be fun and awesome for everyone. This isn’t the Super Bowl or a UFC Title Fight. It’s sex, and it’s as natural as eating and breathing.

Accept who you are, challenge your beliefs, grow, change, and evolve. Everyone has insecurities, both men and women. It’s a normal part of the human experience, but always remember you can make your lot better and be proactive in challenging it. You don’t have to let insecurities consume you or define your character or your identity.

‘Til next time… Take care for now, we’re always here for you guys!


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Rob Virges

Hi, I'm Rob and welcome to our website!

In the last decade I've been coaching men (and women) in the art of connecting and finding love. I can tell you I've been referred to as "an asshole with a heart".

Just like other men who've been trying to figure out and understand the dating game, I used to be socially awkward. I'm a former Dating Mastery Program alumni and CofC apprentice with a decade worth of experience under my belt as a student, coach, and lifestyle mentor. My background is in applied psychology and I utilize a combination academic theory, research, and practical application towards our coaching.

I'm not a creepy pickup artist. I'm a normal guy that's competent, confident, and comfortable with women. My job is simple and that's to understand, nurture, support, motivate, and help you achieve and possibly realize the best version of yourself so you can authentically express yourself, connect with women (or men), and help you achieve whatever your dating goals may be in the most holistic, comprehensive, and practical manner.

Welcome to Craft of Charisma, The #1 company for teaching people to authentically connect, love, and nurture healthy relationships that can last a lifetime.

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