Why Men Can Suck At Dating

Written By: Jeffrey Craig

 About four years ago, I ended the longest relationship of my life. Throughout my whole college career, I never really experienced dating because I was only with one person. Once that chapter of my life came to a close, I was faced with a harsh reality. As a newly single man in the world, I hadn’t the slightest clue on how to attract or date women.

Completely lost on how to live as a single man, I sought out guidance from friends and peers. It was through this search that I discovered the art of “pickup.”

In the beginning, I immersed myself in the pickup culture. I read every book, watched every video, and went out every single night to clubs and bars. Soon, I was a pro. Dating seemed easy. I was constantly meeting girls and receiving validation from those who surrounded me. However soon, I began to realize something. None of these women stuck around.

I decided that pickup was not a good long term solution, so then I attempted to be the nice guy. Sadly, this didn’t work either. Women could see my insecurity and need for validation.

I went on to spend the next several months jumping between these two extremes. I would be the bad boy one day and the nice guy the next, even after failing at both. Disappointed and discouraged, I went back to searching for the answers.

The next couple years were spent researching the dating world and investing a lot of time self-reflecting. The result was a disappointing, but obvious conclusion.

Men SUCK at dating.

This may seem a bit harsh, but it is the ugly truth of it all. Although men themselves are partially to blame, society plays a crucial role in the demise of men in the dating world.

Although there are numerous reasons why men suck at dating, there is also a spark of hope.

First, lets get into the good stuff. Why do men suck at dating?

Pickup Game

Developed in the late 90s, the pickup culture really began to take off in the early 2000s. The art of “pickup” contains a series of social techniques catered toward teaching men how to manipulate women into sleeping with them.

Yes, I used the word manipulate. At first glance it just seems like pickup teaches men social skills in talking with women, but really, it centers around using women’s own insecurities against them. It tricks women into believing a man is someone of value when in fact, they are being inauthentic the whole time.

Pickup did well, for a while. This industry generated billions of dollars worldwide from men wanting to become a modern day Casanova.

Eventually, things began to backfire. Men were sleeping with women, but still weren’t happy. They gained confidence with women, but were not confident in being themselves. Men were getting dumped by their girlfriends once they found out it was all a facade. Women began to learn about pickup and the tools of manipulation. And soon, the pickup game lost its fire.

I personally got sick of putting on a mask of who I was every night to gain a woman’s attention. Any girl I attracted using pickup wasn’t really interested in me. Instead, they were interested in the person I was pretending to be. They were attracted to the lines I used, the way I dressed, the pseudo persona I presented to them. Feeding off women’s insecurities wasn’t fun either. I would wake up the next day feeling like a horrible person. There is no joy to be had by bringing someone else down.

Still, despite my realization and the realization of many others, some men today still attempt to use the old techniques of pickup, only to find that they rarely work. And even when they do, it still doesn’t bring them satisfaction.

Mr. Nice Guy

In order to combat the the misogynistic nature of the pickup culture, a more recently developed trend among the male dating culture has developed, the “nice guy.” The nice guy is the proverbial floor mat in the relationship. He hopes to win a woman’s love and affection by submitting to her will.

The nice guy has great intentions, but sucks at dating because he is not being authentic. He is overly considerate and fails to take initiative when the opportunity to make a move arises. The nice guy exists on the opposite side of masculinity by becoming overly sensitive and submissive.

When I was the nice guy, I would spend the whole date asking about the woman. I would have her tell me her life story. I would flood her with compliments. I would let her pick the date venue. As they caught wind of my nice guy vibe, they would instantly lose interest and respect toward me.

The problem with a nice guy is not that he cares, but that he cares too much. The whole weight of a relationship is put on the woman. The nice guy needs her constant approval and acceptance in order to feel satisfied. This is an immense amount of pressure to put on a woman and also screams codependent.

As a result, most nice guys get gently placed in the friend zone by the women they date. This is where they remain with the constant hope that one day their nice guy approach will finally get recognized and they will receive the love and acceptance they so desperately need.

Online Dating

With the constant rise in social media activity, online dating has now become a socially acceptable form of communication for men and women. With this overwhelming burst in popularity, women everywhere are drowning in messages from hundreds of men a day, all fighting to gain their attention.

I remember being so discouraged by online dating in the beginning. Knowing that these women had their pick of the litter was a difficult pill to swallow. I was in competition with men who had six packs, fancy cars, and considerable wealth and prestige. Instead of recognizing my own value, I thought I had to be extreme with my profile and introductions in order to stand out from the crowd. It appears I wasn’t alone.

The reason men suck at online dating is because they are still trying to use the techniques of pickup. With the internet at their fingertips, a simple Google search leads men to pickup material that teaches them tips on how to gain a girl’s attention on dating sites. Some people out there are still trying to capitalize on men who are desperate to gain success in online dating. Pickup has evolved into the social media realm. Books on pickup techniques for Tinder, Plenty of Fish, etc. are gaining traction daily, despite the fact that the past has proven these techniques don’t work in the long run.

The result is numerous men running the same lines on the same girls over and over again. This prevents them from standing out. Instead, they blend in with every other guy in the crowd. To top it off, even when they do make an impression and land a date, the girl is disappointed to find that the person who attracted them online is not who they are in person.

It is challenging enough to gain the attention of a beautiful woman online who now has instant access to her pick of the litter. Men are simply shooting themselves in the foot by adopting practices that have been proven not to work.

Societal Stigmas

Another reason men suck at dating is because they have embraced society’s standard of masculinity. Just like women, men face an immense amount of pressure to embody what it means to be a masculine male.

The result leaves men believing that they will only find happiness and self worth by sleeping with as many beautiful women as possible. They have been conditioned to think that one can only reach fulfillment when they live the life of a playboy.

Where society shames women for their sexuality, it exploits it for men. Men are told that the desire for a meaningful emotionally committed relationship is a sign of weakness. Yet they are praised by society and their peers when they succeed at bringing a woman to bed with them.

Men hide what truly lies in their heart out of fear of being ridiculed. And instead, they wear a mask hoping they can convince the world and themselves that this is what they truly want.

Most Men Are Still Boys

Many men suck at dating because they are still a boy. The newer generation of men have been robbed of their proper right of passage. They have not truly experienced the internal transition from boyhood to manhood. Instead, they have been fed false rights of passage that have led to negative consequences in their dating life.

These “boys” have been told that manhood starts the first time they have sex with a woman, when they start their first job, when they buy their first property, and the list goes on. However, these are all external experiences. Not one of them require any internal change.

At the all boys Catholic high school I attended, boys were desperate for a right of passage. They would put an immense amount of pressure on themselves to have sex, grow facial hair, and show off their (or their parents’) financial status. They didn’t have a rite of passage so they looked toward society’s definition of what a man is and emulated that instead.

A true right of passage only occurs internally. It is an enlightening, an awakening, a spiritual transformation of the self. Without this internal awakening, men continue to live as boys.

Low Self-Esteem

Despite the confident facade that they project out into the world, most men actually have a low self-esteem. There has been an overwhelming surge in physical, social, and occupational expectations in men.


Men have been told that they will not be appealing to women unless they look like they belong on the cover of a fitness magazine. The result is men dedicating most of their day to obsessing over their physical appearance. Even the men who achieve an impressive physique still compare themselves to men who are even more “ripped” than they are. The expectation for physical perfection leaves men feeling undesirable or instills the belief that their only desirable trait is their physical appearance.


Men have also been conditioned to be the alpha-male of their social circle. This has been around for years, yet has gotten progressively worse over time. Men have been told that their appeal is based on their position in the social hierarchy. As a result, men submit themselves to pissing competitions to prove their masculinity. The unfortunate aspect of this is that by proving how alpha they are, they actually are proving the opposite. Instead of men showing their masculine superiority, the reveal just how insecure they are about themselves and just how desperate they are to gain social approval.


With the rise of women in the workforce over the last several years, men are under more pressure than ever to be financially stable. For decades, men dominated the workforce, being the sole breadwinners of the household. The ability to provide for the family was a testament to a man’s masculinity. Now that women are working high paying jobs, that masculinity is being challenged. For years, men have been told that their value is based on income. Now, men are so desperate to be considered desirable, that they are sacrificing their own dreams and passions for a higher paycheck.  These men fantasize about the celebrity lifestyle. They associate financial income with desirability. Instead of working at something they love, they are working to earn love. When these men fail at reaching financial success, they are left feeling emasculated and empty.

Why do you ask does this have anything to do with why men suck at dating?

Well, these expectations men put on themselves result in a low self-esteem. When men don’t have the million-dollar job, the perfect body, and social superiority, they are left feeling unworthy of a woman’s love. Women have an amazing ability to sense insecurity and these men show their hand without having to speak a word.

The Underlying Message

So now that we know why men suck so bad at dating, what’s to be gained from all of this? If you take a step back and take a look at the big picture, there is one common thread found in each section.

Men need to define their masculinity for THEMSELVES.

From learning how to date women to defining what it is to be a man, the main reasons men suck at dating is due to what society has told them to be.

Men suck at dating because they are inauthentic. They lack a sense of purpose, confidence, and self-compassion. They have been fed that their heart lies to them and that masculine stereotypes hold the key to self-fulfillment. Yet, time and time again, this is proven to be false.

The true answers lie within each man. When they look inside themselves, they will find who they are, who they want to be, what brings them fulfillment, and how they express their masculinity to the world.

When men free themselves from the shackles of societal expectation and allow themselves to embrace who they truly are, they will no longer find dating to be difficult, but actually fun.

Dating is about connecting with women, getting to know one another, and discovering a partner they are compatible with.

Self discovery will not make a man more desirable to all women, but that is not the point. Instead, by living as who they truly are, men open themselves up to attracting the RIGHT woman. By defining masculinity for themselves, men are granted the freedom to approach dating for what it truly is, a valuable and enjoyable experience.


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