The 5 Most Common Insecurities In Men (And How To Overcome Them)

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It should come as no surprise that confidence is a big deal when it comes to success at dating. Confidence, after all, is sexy.

The problem of course, is that confidence can be hard to come by. Confidence boosting is a big-money industry these days. Even the Pick-Up Artist community is flooded with products designed to help men with what they call “inner game” issues. But for all for all of the times we wrestle with issues of deservedness or a scarcity mentality, there are certain areas where men are just especially vulnerable.

Men are more sensitive than culture gives them credit for. For all of the proclamations of manliness and machismo and how men just don’t worry about the same things that women do, the male ego is surprisingly fragile. We may be able to endure the jocular insults and shit-talking that are often part and parcel of male friendship but there are certain areas that are just off-limits. They’re little emotional Van Der Graaf generators of anxiety that serve to wreck a man’s self-esteem, prompting him to throw hundreds or thousands of dollars towards any snake-oil or hokum that promises to fix the issue.

“Now with 100% more bullshit!”


The problem is, of course, in your head rather than on it… or in your shorts, for that matter. But let’s look at the top 5 most common insecurities in men… and talk about how you can overcome them.

#5: Your Body

For decades, feminists lamented the damaging power of the Male Gaze and the toll that it’s taken on women’s self esteem and health, and it seemed to be profoundly one-sided; Naomi Wolfe wrote in The Beauty Myth that men would never fear being objectified in the way that women are.

Fast forward 20 or so years and suddenly eating disorders and body dysmorphia are on the rise in men1 and liposuction is one of the fastest-growing plastic surgery procedures performed on men. Men have suddenly realized that – contrary to a lifetime of being told that men are visual while women are intellectual – women like to look too. For the first time in generations, women are openly ogling men the way that we’ve been drooling over women and it makes us profoundly uncomfortable. And now that men have realized that women are having the screaming thigh-sweats over Ryan Gosling’s abs, we feel like we’re not measuring up.

God fucking damn it, it’s not fair!

We’re worried that we’re too fat, too thin, too hairy, too tall, too short, too… something. And it’s driving us to dangerous levels of desperation trying to match up with a societal ideal.

How To Get Over It:

Well to start with, eat healthy – decrease the level of simple carbohydrates, up your intake of green leafy vegetables, avoid excess fats and sugars and processed foods – and start getting more active. A healthier diet and increased exercise will increase your baseline health and make you feel better over all. It doesn’t necessarily mean you have to hit the gym – and in fact, there are plenty of people who are just not suited for traditional exercise routines. If you’re the sort of person who couldn’t dream of spending 20-30 minutes on the elliptical runner every day, find another way of getting active that you enjoy. Play pick-up games of basketball after work. Join a dojo and start studying martial arts. Get into swing or salsa dancing. Work towards a goal such as the Couch to 5K program or train for the zombie apocalypse by training for the Run For Your Life races. Your local gym will also have any number of classes; don’t dismiss them as being “too girly” – that Pilates class will beat your ass into painful submission and laugh at you all the while.

Of course you also have to realize that just because you’re eating right and exercising doesn’t mean that you’ll magically become a Men’s Health cover model. To start with, you’re restricted by your genetics and build – not everybody is going to have those perfect six-pack abs no matter how much they work out. In addition, those shirtless dudes you see in ads, on covers and in the movies don’t live the same lifestyle you do. Their job is literally to look good – their day to day life is entirely structured around the routines and meals that it takes to look like that. You simply don’t have the same time to commit that they do.

Not to mention how much of it is smoke and mirrors. You’d be amazed what you can do with basic make-up tricks, lighting and dehydration long before you get into Photoshop.

What you need to do is learn to accept who you are -and, more importantly – that you don’t need to live up to some bullshit ideal in order to be attractive. Just as men love a wide range of body types and shapes, so do women. There are women out there who like big, burly, hairy, men. There are women who like skinny ectomorphs. Accepting your build for what it is, instead of trying to force yourself to live up to a physical ideal that you literally cannot match, will do wonders for your esteem. Wearing clothes that fit properly will help improve your look no matter what kind of body you have.

And let’s face it: if a woman’s into you enough to come home with you, she’s not going to worry that you’re not a cinema idol. By the time sex is in the equation, it’s fait accompli.

#4: Your Finances

For generations, part of how men have identified themselves has been as The Provider – your ability to care for and support your mate has been a measure of manliness since time immemorial. As a result, men as a group put an inordinate amount of importance on money and material goods; witness every song or music video whose main narrative is “I’m so fuckin’ rich I can have any woman I damn well feel like.”

Now let’s be honest: money may not buy you love, but it certainly improves your bargaining position. There’s no denying that material wealth is attractive, even if the woman in question isn’t a gold digger.

To be fair, money *does* make being a dickbag more tolerable to women.

Obviously, 99% of us2 aren’t crazy rich and we never will be, but somehow there are still people who aren’t Donald Trump who are having plenty of dating success even with their middle-class lifestyles. You don’t have to be crazy-stupid rich in order to find love or a relationship.

But what if you’re not even middle class? What if you’re stuck with public transportation, a minimum wage job, a shitty apartment  and a “ramen-five-nights-a-week” diet? What then? How can you expect to find a girlfriend then? What woman is willing to put up with riding the bus to your very-occasional dinner out and your once-a-month-maybe movie date?

How To Get Over It:

First of all, look around. The economy is in the fucking tank. We’re all floundering around trying to find work and having to scrape to make ends meet. We’re all having to deal with tight financial times, and any woman worth dating is going to understand that. If the women you like are looking as much at your bank account as they are at your personality, you really need to quit dating shallow materialistic bitches and date women who appreciate a man who has more going for him than a fat wallet.

Now, if you’re doing badly, financially, because you’re lazy or have no ambition, that’s one thing. That’s an unattractive trait no matter what your take-home pay rate is. Women like a man who not only has goals and ambition but who is actively working towards them. Drive and determination are incredibly attractive traits.

Being on a tight budget doesn’t mean that you can’t look good or treat a woman to a good time. To start with, you can find awesome clothes on a budget. Learn to harness the power of the Internet – you’d be surprised at the discounts that you can find with some Googling and a little skill on eBay. Learn how to work the sales. And again: make sure your clothes fit. A proper fit makes all the difference.

Never forget: romance is more than material goods or price. It’s about spontaneity, personality, atmosphere and attitude. You can date without breaking the bank; there are plenty of dates that are awesome that won’t cost you a small fortune. A romantic home-cooked meal by candlelight will mean more to the right woman than impossible-to-get reservations at that exclusive French bistro. Museums and art galleries make for amazing low-cost dates that are classy as fuck. You can also find a surprising number of free or low-cost events in your town, especially if you’re in a college town if you do some research.

Don’t worry too much about your finances. Any woman worth your time will be won over by your caring personality, wit and charm and sexiness.

Speaking of which…

#3: Your Hair

The level of importance men put on their hair would astound most women. We like to pretend that all the care we put into our hair care is to shake our heads a couple of times on the way out of the shower, but a man’s hair is one of the most visible symbols of his potency and masculinity.

Which of course, means that thinning or receding hair is proof of God’s hate.

A man with thinning hair or a receding hairline  – or worse, one who’s bald – is seen as a man who is long past the flush of his youth. He’s someone whose best years have passed him by and is now left with nothing but comedic attempts to try to disguise his loss with gimmicks, props and medication. The image of a balding man is one of comedy and impotence as he tries to disguise his pate with a creative arrangement of what little hair he has left. We laugh at the Hair Club for Men commercials that run on late night TV. “I’m not just the president, I’m a client” is a punchline, right up there with a man losing his toupee at a critical moment. Even the ancient Romans had a saying: “Never trust a bald man with hair.”

If you don’t have a head of thick, luxurious hair, you’re just less of a man, right? Right?

How To Get Over It:

Allow me to introduce you to my counter-argument. Mr. Statham, meet my readers. Readers, Mr. Jason Statham.

“Feck ahf!”

Let’s not kid ourselves: bald is sexy.

The cause for the most common cause of male hair loss isn’t known; it’s theorized to be a combination of genetics and hormonal levels in men. The best thing that you can do if you’re faced with hair-loss is face it like a man.

You can always take the medical route;  Rogaine can slow the loss and Propecia can help you regrow your hair – if you’re willing to risk the potential side-effects, which include depression, erectile disfunction and a decreased ability to ejaculate, which sound like a cure that’s worse than the disease.

If you have a nicely shaped skull – one that’s fairly symmetrical without any dents or bulges – you can always bite the bullet and shave your head. It will take practice and daily maintenance but many, many women appreciate the feel of a freshly shaved scalp. If you don’t want to go the full-shave route, do your dignity a favor and start adopting a short hair style; a close crop will minimize the appearance of balding and provide the illusion of volume. Don’t make the mistake of trying to grow your hair longer and fluff it in order to try to hide your bare patches; you’re not fooling anyone and it just looks silly.

While you’re at it, consider facial hair: a short, neat beard or goatee will pull attention away from your crown and towards your face instead.

#2: Your Sexual Ability

Sex causes an absurd level of anxiety in men. We’re forever worried about when we should expect sex or whether we’re pushing too hard for it. We obsess over how we measure up to a woman’s past lovers or how many partners we’ve had versus how many partners she’s had. Spit or swallow? Did we get off too quickly? Did she get off at all? Are we rocking her world or is she just counting the ceiling tiles? OH GOD OH GOD OH GOD.

It gets even more insane when you throw porn into the mix. Now suddenly not only are we worried about whether we’re the best lover she’s ever had but men are worried about such things as whether to aim for her boobs or her face or the volume of his ejaculation. That’s right, if you can’t paint a Jackson Pollock on the wall with your sperm, you are not a man.

You can thank me for that mental image later.

How the hell are we supposed to get our freak on if we’re too busy worrying about being labeled “Two-Stroke Tony” to all of her friends?

How To Get Over It: 

Well to start with, quit assuming that porn resembles real sex at all. Fucking in porn is  kabuki – it’s an incredibly stylized and exaggerated performance and the only relation it bears to actual, every-day sex is that tab A goes into slot B. Trying to translate porn sex into the real world is an exercise in pain and frustration… literally. Porn actors have to position themselves into incredibly uncomfortable poses in order to be open to the camera and the “money shot” only developed because it was a way of confirming that yes, the male actors are actually ejaculating at all. Basing your ideas ande expectations about sex from porn is a mistake.

Becoming a masterful lover has two major components: you need to be patient and willing to take direction as needed. Everything after that is just a matter of practice. Every woman is different and will have different requirements for proper bed-rocking-brag-to-all-her-friends-later-sex. Want to know what it takes to rock her world? Ask her what she likes. Learn how to read her signals and respond to them. If you’re trying to use your patented swirly-go-round technique and she’s giving you the tap, trying to push you away or clamp her legs shut, then don’t ignore her. Just because your last girlfriend loved that trick you did with your thumb doesn’t mean that every woman will and trying to power through someone’s “fucking stop” signals is only going to ensure that you’re never invited back for another go-round.

Oh, and when in doubt: more foreplay. Always err to more foreplay.

But while we’re talking about sex, let’s talk about

#1: Your Penis

The size and shape of a man’s penis is the number one source of any man’s insecurities and fears and we all have the clogged spam folders to prove it. Circumcised or natural, growers or showers, curved or straight…  every man alive has had anxious questions as to how he measures up and whether his is unusual or otherwise just wrong. Penis size is popularly associated with virility and sexual desirability. A man with a small penis is just not as “manly” as someone with a ten inch monster. If you’re not long, hard as steel, ramrod straight and aiming straight at the ceiling, you’re just an evolutionary dead-end, doomed to a lifetime of pointing and derisive laughter from the hordes of women you will never, ever be able to satisfy. Am I right, or am I right? Back me up here guys.

How To Get Over It:

Well, let me start out by introducing you to a friend of mine. Mr. Jeremy, if you would please…


Really, his existence alone should kill the myth that penis size somehow automatically translates into sexual desirability or manliness.

Look, cock size is subject to the same whims of fashion and popular culture as everything else. Just as there was a period where plump women were the height of beauty, there have been long periods in Western culture where a smaller, uncircumcised penis was the ideal; larger penises were thought to look grotesque and to be a sign of low breeding and intelligence while circumcised penises just looked weird.

The hard (ha!) and fast truth is, the average penis length is 5.1 inches erect when measured from the base and approximately 1.5 inches in diameter. Bigger doesn’t automatically equal better in this case; the longer a penis is, the more likely the odds are that that you’re going to end up bumping up against your partner’s cervix, which is not fun for her. Girth is actually far more important for sexual pleasure; all of the important nerve endings are actually located near the front of the vagina and clustered in the clitoris.

If you feel like you don’t measure up – as it were – there are things you can do to make it look bigger. Losing weight will make you look bigger as the pads of fat around it shrink and pull back. Think of it like tides; when the tide rolls out, the beach looks way bigger. Similarly, some judicious manscaping of your pubes with a body hair trimmer will make your penis stand out and seem larger. You can’t actually increase your penis size through surgery or medication; the pills are bullshit and the surgery involves cutting the ligaments that connect your penis to your abdomen which will make it harder for you to maintain an upright erection.

Getting back to Mr. Jeremy: he may have a giant cock, but there are also porn stars who have contracts that specify “No bestiality, no gangbangs, and no scenes with Ron Jeremy.” Yes, there will be size-queens – both men and women – who will judge a man by his cock size. Let’s be honest: you don’t want to date them in the first place even if you’re hung like a bull moose.

The best thing you can do, however, is to accept what you’ve been gifted with and learn how to use it. Many women out there actively dislike men with huge cocks. These hung studts tend to think that their size will do all the work for them and slam away mechanically without any skill or style at all. A man with a more modest endowment is far more likely to know how to use it properly. A man with two hands, a tongue and a can-do attitude will always be more in demand, sexually, than somebody who thinks that pounding away like a piston in an industrial film is the end-all/be-all of sex.

Which would you rather be? The guy with a huge penis who doesn’t know what he’s doing or the guy with a more modest endowment whose partners brag about every chance they get?



  1. although frankly, calling it cutesy names like “manorexia” or “bro-lemia” really minimize the seriousness of the issue, for both men and women []
  2. Hey look, I’m relevant! []

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