Why It’s So Hard: The Guide To Modern Dating

When you think about it, despite feeling difficult, the problems men struggle with in dating sound pretty trivial.

For instance, men have been walking and talking their entire lives, yet walking up to an attractive woman and opening their mouths to say “Hi,” can feel impossibly complex to us. Men have been using a phone since they were children, yet the agony some men go through just to dial a woman’s phone number, you’d think they were being waterboarded. Most men have kissed a woman before and they’ve seen hundreds of movies and instances in real life of other people kissing, yet as she stares dreamily into his eyes hour after hour, he tells himself he can never find the “right moment” to do it.

Why? It sounds simple, but why is it so hard?

There are men who have built business empires, gone to war, played violent sports, climbed mountains, written novels — and yet the mere sight of a petite woman in a sexy dress sends their hearts racing and minds reeling.

Dating advice often compares improving with women to improving at some practical skill, such as playing piano or learning a foreign language. Sure, there are some overlapping principles, but I can’t imagine a grown man trembling with anxiety every time he sits down at the keys. And I’ve never met a man who became depressed for a week after failing to conjugate a verb correctly. They’re not the same.

Generally speaking, if someone practices piano daily for two years, he will eventually become quite competent at it. Yet a number of men continue to go out meeting woman after woman, going on date after date, year after year and seeing little to no progress, little to no change, and continue to remain alone.


What is it about this one area of life that the most basic actions can feel impossible, that repetitive behavior often leads to little or no improvement, and that our psychological defense mechanisms run rampant trying to convince us to NOT pursue what we want?

Why dating and not, say, skiing? Or even our careers? Why is it that a man can conquer the corporate ladder, become a militant CEO, demanding and receiving the respect and admiration of hundreds of brilliant minds, and then at night cower and stutter his way through a date with a beautiful woman?


As children, none of us get 100% of our needs met. This is true of you. It’s true of me. It’s true of everyone. The degree of which our needs aren’t met varies widely, and the nature of how our needs are unfulfilled differs as well. But it’s the sad truth about growing up: we’ve all got baggage. And some of us have a lot of it. Whether it is a parent who didn’t hold us enough, who didn’t feed us regularly enough, a father who wasn’t around often, a mother who left us and moved away, being forced to move from school to school as a child and never having friends — all of these experiences leave their mark as a series of micro-traumas that shape and define us.

The nature and depth of these traumas imprint themselves onto our unconscious and become the map of how we experience love, intimacy and sex throughout our lives.

If mom was over-protective and dad was never around, that will form part of our map for love and intimacy. If we were manipulated or tormented by our siblings and peers, that will imprint itself as part of our self-image. If mom was an alcoholic and dad was screwing around with other women, it will stay with us. If our first girlfriend died in a car accident or dad beat us because he caught us masturbating — well, you get the point. These imprints will not only affect, but define, all of our future romantic and sexual relationships as an adult.

You and I and everyone else have met hundreds, if not thousands, of members of the opposite sex. Out of those thousands, multiple hundreds easily met our physical criteria for a mate. Yet out of those hundreds of women, we only fall for a very few. Only a handful we meet in our entire lives ever grab us on that gut-level, where we lose all rationality and control and lay awake at night thinking about them.

It’s often not the woman we expected to fall for either. Susy had the perfect body. Jane had the great sense of humor and was amazing in bed. But Melissa is the one we can’t stop thinking about, the one we involuntarily keep going back to over and over and over again.

Psychologists believe that romantic love occurs when our unconscious becomes exposed to someone who matches the archetype of parental love we experienced growing up, someone whose behavior matches our emotional map for intimacy. Our unconscious is always seeking to return to the unconditional nurturing we received as children, and to re-process and heal the traumas we suffered.

In short, our unconscious is wired to seek out members of the opposite sex who it believes will fulfill our unfulfilled emotional needs, to fill in the gaps of the love and nurturing we missed out on as kids. This is why the people we fall in love with almost always resemble our parents on an emotional level.

Hence why people who are madly in love say to each other, “you complete me,” or refer to each other as their “better half.” It’s also why couples in the throes of new love often act like children around one another. Their unconscious mind can’t differentiate between the love they’re receiving from their girlfriend/boyfriend and the love they once received as a child from their parents.

This is also why dating and relationships are so painful and difficult for so many of us, particularly if we had strained familial relationships growing up. Unlike playing the piano or learning a language, our dating and sex lives are inextricably bound to our emotional needs, and when we get into potentially intimate or sexual situations, these experiences rub up against our prior traumas causing us anxiety, neuroticism, stress and pain.

So that woman rejecting you when you approach her isn’t just rejecting you, but to your unconscious you’re reliving every time your mother rejected you or turned down your need for affection.

That irrational fear you feel when it comes time to take your clothes off in front of her isn’t just the nervousness of the moment, but every time you were punished for sexual thoughts or feelings growing up.

Don’t believe me? Think about this. Someone no-shows for a regular business meeting with you. How do you feel? Annoyed likely. Maybe a tad disrespected. But chances are you get over it quickly, and by the time you get home and are watching the football game you don’t even remember it even happened.

Now, imagine a woman you are extremely attracted to no-shows for a date. How do you feel? If you’re like most men who struggle in this area of their life: like shit. Like you just got used and lead on and shat on.

Why? Because being flaked on rubs up against your unconscious fear of abandonment, fear that nobody loves you and that you’re going to be alone forever. Ouch.

Maybe you freak out and call her and leave her angry voicemails. Maybe you continue to call her weeks or months later, getting blown off over and over again, feeling worse and worse each time. Or maybe you just get depressed and mope about it on an online forum, asking for strategies or tactics to prevent it happening in the future.

Every irrational fear, emotional outburst or insecurity you have in your dating life is an imprint on your emotional map from your relationships growing up.

It’s why you’re terrified to go for the first kiss even though she’s sent you 100 signals saying she likes you. It’s why you freeze up when it comes time to introduce yourself to a woman you don’t know or tell someone you just met how you feel about them. It’s why you can’t perform when you get into bed with her or why you avoid opening up and sharing yourself with her.

The list goes on and on.

All of these issues have deep-seated roots in your unconscious, your unfulfilled emotional needs and traumas. Pick up lines, techniques and theory don’t fix them either, they merely cover them up.


A common way men bypass dealing with the emotional stress involved in dating is by disassociating their emotions from women and sex. If they shut off their need for intimacy and connection, then their sexual actions no longer rub up against their emotional maps and they can greatly diminish the neediness and anxiety they once felt around women while still reaping the superficial benefits. It takes time and practice, but once disassociated from their emotions, they can enjoy the sex and validation of dating women without concerns for intimacy, connection, and in some cases, ethics.

Here are common ways men disassociate dating from their emotions:

Objectification of sex and women. This includes, but is not limited to, keeping lay counts, flag counts, rating women they date on a 1-10 scale, tracking “progress,” calculating open ratios, close ratios, comparing notes with other men and treating it as some sort of high score on a video game.Granted, meaningless sex can be fun at times. So can a harmless brag to your buddies here and there. But viewing ALL male-female interactions through this lens is catastrophic to one’s ability to engage in emotional intimacy and resolve a lot of these unconscious problems. In fact, it just suppresses them and makes them worse.

Misogyny. Viewing women as inferior or as highly different creatures with different values, desires and emotions is a sure way to redirect one’s emotional problems outward onto the female population at large rather than dealing with them yourself. Without fail, men who treat and view women as some inferior “other,” are more often than not projecting their own anger and insecurities onto the women they meet rather than dealing with them. (For what it’s worth, this applies to some misandrist feminists I’ve come across as well).

Manipulation, lines and tactics. By adopting lines, manipulation or tactics to meet and seduce women, a man is withholding his true identity from the woman and therefore is withholding his emotional map as well. If a woman is falling for the perception of who he is rather than who he really is, then there’s far less risk for conjuring up the buried emotional stress and pain of his prior relationships.

Overuse of humor, teasing, bantering. A classic strategy of distraction. Not that jokes or teasing aren’t always bad, but an interaction of NOTHING but jokes and teasing is a means to communicate without saying anything important, to enjoy yourselves without actually do anything, and to feel like you know each other without actually knowing a thing. This is most typical of English-speaking cultures, as they tend to use sarcasm and teasing as a means to imply affection rather than actually showing it.

Stripclubs, prostitution, pornography. A way to experience one’s sexuality vicariously through an empty, idealized vessel, whether it’s on a screen, a pole, or running you $100 an hour.

Men who harbor a lot of resentment for women tend to disassociate and objectify women the most. Men who had turbulent relationships with their mothers, men who were left by their wives or girlfriends, or men who were tormented by women growing up, these men will likely find it much easier and more enticing to objectify and measure their sex lives than to confront their demons and overcome their emotional scars with the women they become involved with.

Depending on the nature of their issues with women and their upbringing, these men can become either Fake Alphas or Nice Guys. On the surface these two types of men appear quite different (one over-compensates and is domineering, the other is wussy and passive aggressive). But honestly, they’re more or less the same guy – one’s narcissistic, the other’s codependent; one gets laid, the other jerks off to Hentai between World of Warcraft sessions.

Note: This isn’t to say that many women don’t disassociate their emotions and objectify men as well. But there’s a lot more social pressure on men to ignore their emotions, particularly “weak” emotions such as a need for intimacy and love. It’s more socially acceptable for men to objectify their sex lives and boast about it. Whether you think that’s right or wrong or doesn’t matter, it is how it is.

Obviously, it goes unsaid that Pick Up Artist tactics promote objectification front and center as part of their strategies. It helps emotionally damaged men get short-term sexual results with as little hassle as possible. But PUA teachings don’t solve the root problem. They just cover it up. They’re a temporary fix at best, and even more damaging at worst.


Disassociating from your emotional needs is the easy way out. It requires only external effort and some superficial beliefs. Working through your issues and resolving them requires far more blood, sweat and tears. Most men aren’t willing to dig deep and put in the effort, but it yields far greater and permanent results.

1) The biggest misconception when it comes to working through an excess of emotional baggage is that these feelings ever completely go away. Research and brain imaging indicates that fears, anxieties, traumas, etc. are imprinted on our brains in similar ways that our physical habits are. Just like you’ve developed a habit of brushing your teeth every time you wake up, you have emotional habits of getting sad or angry any time you feel abandoned or unwanted.

The way to change is NOT by removing these feelings or anxieties altogether, but rather consciously replacing them with higher order behaviors and feelings.

This can ONLY be accomplished through taking action. There is no other way. You cannot rewire your responses in healthy ways and confront your insecurities if you aren’t out there actively pushing up against them. Trying to do so is like trying to learn how to shoot free throws left-handed without ever actually touching a basketball. It just doesn’t work.

If you have a habit of flipping out and leaving angry voicemails every time a woman doesn’t call you back, you don’t get rid of the anger, but rather channel that anger into a better and healthier activity, like say, going to the gym, or painting a picture, or punching a punching bag.

2) Anxieties can be overcoming through utilizing implementation intentions and progressive desensitization. For instance, if you have a problem getting sexual or making the first move with women, start with baby steps. Tell the next woman you go on a date with that she’s sexy. Once that feels comfortable then challenge yourself to have a conversation about sex. After that challenge yourself to hold hands with a woman. Then challenge yourself to kiss a woman.

I’ve set up online programs that utilize progressive desensitization to help men overcome their anxieties around women.

Obviously this takes time and requires consistently facing situations which make you uncomfortable, but that’s the idea. You must overlay old emotional habits of fear and anxiety with new healthier ones of excitement, boldness and assertiveness. Mentally train yourself so that any time you feel anxiety, you force yourself to do it anyway.

3) The final step — once you’ve learned to channel your negative emotions in constructive ways, once you’ve eaten away at your anxieties and are able to often act despite them — is to come clean with women you see about your needs and start screening based on them.

For instance, I’ve always had a fear of commitment and needed a woman who was comfortable giving me space and some freedom. Not only do I openly share this with women I get involved with now, but I actively screen for women with these traits.

Ultimately, your emotional needs will only be fully met in a loving and conscious relationship with someone who you can trust and work together with – and not just your emotional issues, but hers as well. We unconsciously seek out romantic partners in order to fulfill our unfulfilled childhood needs, and to do so cannot be completely done alone.

This is the reason that honesty and vulnerability are so powerful for creating high-quality interactions – the practice of being upfront about your desires and flaws will naturally screen for those women who best suit you and connect with you.

This kind of authenticity changes the whole dynamic with women. Instead of chasing and pursuing, convincing and persuading, you focus on consistently improving yourself and presenting that self to the women of the world. The right ones will pay attention and stay. And whether you spend a night or a year with them, this enhanced level of intimacy and mutual vulnerability will help heal your emotional wounds, help you become more confident and secure in your relationships and ultimately, overcome much of the pain and stress of that accompanies sex and intimacy.


I invite you to post in the comments below what your emotional hang ups are in this area of your life, where they probably come from, and how you could overcome them in an open and honest way.

As an example, I grew up in a broken family where all members isolated themselves and we communicated our emotions very seldom. As a result, I became highly sensitive to confrontation and any negative emotions of others. I became the consummate Nice Guy and for years struggled to assert myself in my relationships and around women. In fact, I objectified my sex life quite a bit and adopted some narcissistic behaviors in order to push me through some of these insecurities.

My fear of commitment is undoubtedly rooted in my parents’ divorce and my knee jerk reaction for years was to run away any time a woman attempted to get close to me. I slow eroded that fear by opening myself up to intimate opportunities little by little over a long period of time. I was incapable of becoming intimate with a woman unless I had an escape route (i.e., she had a boyfriend, or I was going to move to another city soon, etc.).

Spending all of my adolescence living alone with my mother has made me particularly sensitive to female affection, and like a smoker rationalizing reasons to smoke one last cigarette, I have often rationalized myself into intimate and sexual situations with women who I perhaps should not have been with or didn’t actually like as much as I thought I did.

This is my emotional map — at least part of it. These are the hang ups and issues that I’ve battled and slowly beaten back with years of active effort. These are the realities that I express openly and seek out the proper women who can handle them.

What are yours? Thought Catalog Logo Mark

This post originally appeared on POSTMASCULINE.

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