This Is Why You Fail (Or: What’s Holding You Back In Dating)

Let me paint a common story for you: It’s been a while since you’ve started trying to get better at dating and it seems like you’re no further along than you have been before. If anything, you’re actually getting worse. The more posts you read, the more approaches you make… none of it seems to be working. You’ve plateaued. You’ve stalled out. You’re not getting any responses from your online dating profile. You’re getting nowhere meeting people in person.

You’re angry.

You’re depressed.

You’re frustrated.

The longer this goes on, the more you’re becoming convinced more than ever that this whole dating/sex/talking to other people thing is something that other people do and you’d be better off weighing the pros and cons of a monastic life of quiet desperation and a poetic death via alcoholism interspersed with self-pitying and slightly arch animated gif parades on Tumblr1.

“Thanks Doc, you’re really helping here.”

In short: you’re failing miserably and you don’t know why.

Trust me, I know that feeling; it’s something everybody goes through when you’re trying to get better at anything, especially something as personally defining as dating and relationships. As far as I could tell, I was doing everything right, so why the hell was I fucking up every. God. Damn. TIME??

Well, as it turns out, it wasn’t a case of my technique being bad2 or women being bitches or any number of other things I told myself to explain my failures away. I was sabotaging myself in a number of ways that I didn’t even realize… and until I took the time to recognize this and actually address these issues, I was never going to get better.

Over the years I’ve seen these issues crop up again and again; I’ve seen them in friends, in the letters I’ve gotten as Dr. NerdLove, even in myself in different aspects of my daily life. The things that hold us back in dating almost always systematically bleed into the other parts of our lives as well and it’s only when we can be honest with ourselves, confront and address these issues that we can manage to move forward and start making the progress we know we can achieve.

So I want to present a list of the most common3 reasons why you fail.

You’re A Bundle of Negativity

As I’ve mentioned before: negativity is a self-fulfilling prophecy.

An attitude of “This sucks, this will never work, I’ll never_______, only _____ people get to do _____,” only guarantees that you are indeed correct; it won’t ever work, nor will you ever do whatever it is that you’ve been hoping. They’re self-limiting beliefs – beliefs that you allow to take over your life and restrict you from achieving what you hope to achieve. Your attitude literally limits you because you make it come true.

When you tell yourself that you will never ________ because only X guys do _______ and you’re not X, you’re artificially cutting yourself off from any and all possibilities. If, for example, you believe that only “alpha” – for a suitably mistaken definition of “alpha” men get women, then that will be part of your reality. Not because it’s true but because that’s what you believe; everywhere you go, you will find continuous “proof” that this is true. Nothing but miles and miles of assholes with the women you want as far as the eye can see…

Or so you think. Your negative belief is causing you to fall victim to a common fallacy  known as “confirmation bias” – the tendency to only notice or pay heed to that which confirms your pre-existing belief. If you believe no woman could possibly find you attractive, you will elide over all evidence to the contrary – women flirting with you, giving you the “come-hither” stare or even just smiling at you – and focus like a laser on every incidence of negativity. You will see every interaction in the worst possible light: “she doesn’t like me, she’s clearly repulsed by me, she’s only being polite, I’m misreading the signals”

This apparently unending stream of reinforcement will only serves to perpetuate a vicious cycle; your self-limiting beliefs cause you to overlook evidence to the contrary, thus reinforcing the belief which, in turn, continues to make it impossible to see the truth. Your negative attitude will seep into everything you do; it will affect your attitude, your self-image, even your posture… all of which will serve to work against you.

You need to make an effort to be positive.

“OK, I’m positive this doesn’t work.”

Breaking negativity can be difficult; it takes time and effort to willfully decide to take a positive attitude and belief and stick to it. But the fun thing about confirmation bias? It works both ways. Believing in yourself – that you’re attractive, that you have a lot to offer others, that you can and will succeed – can actually help you.

Just ask yourself: would you rather a world where everything confirms your worst fears or your fondest fantasies?

You’re Trying To Be Someone You’re Not

There’s a reason why “just be yourself” is one of the most annoyingly useless advice cliches out there. After all, it’s likely that “being yourself” hasn’t exactly gotten you to where you want to be.

But there’s a point to it.

When we look at people who have something we want – whether it be material success, a skill or talent or even just a hot girlfriend – it’s only natural to try to be more like them. Whatever they’ve got going for them worked for them… why shouldn’t it work for you? And after all, whatever you’ve been doing hasn’t exactly been working out for you so far.

The problem with this approach is that, frankly, that’s not who you are. Trying to be someone who is diametrically opposed to who you are inside is a recipe for frustration and failure.

Nowhere was this more apparent than in the early days of the Pick Up community, when people assumed that one of the secrets of success with meeting women is to “peacock”; that is, dress up in exotic or even outlandish ways in order to get attention. Suddenly, you couldn’t swing a dead cat in a bar without hitting someone trying to rock a fuzzy top-hat and black nail polish or a shiny silk jacket, spiky earrings and New Rock boots.

Er… not that I would know anything about that.

The problem of course is that while Mystery was able to get away with dressing like a Hot Topic jumped him in a dark alley, he’s a professional magician; dressing weird comes with the territory. Everybody else was hoping that their outfits were going to do most of the heavy lifting for them and generally looked like idiots.

Similarly, it’s inadvisable for an introverted person to try to force themselves to act like an extrovert, especially in the dating scene. It’s incongruent with who they are; they’re quite literally pretending to be someone they’re not in hopes of better results. Not only will others feel the unnaturalness of their pose, but the stress and strain of keeping up the act only serves to wear them down faster, leaving them drained and upset… and not any closer to finding a date.

Not everybody is built to be a club-hopping player – and yet that’s what PUA culture directs men towards. Not everybody is cut out for traditional monogamy, for polyamory, for kink, for vanilla sex… but that doesn’t stop them from trying to force themselves into the model because they think that’s what they should be.

Using someone as a role-model is a good idea and one I advocate. However, too often we tend to try to model ourselves after what we think we should be like, which is often at 180 degrees from who we really are. Trying to fit into a personality type that’s so diametrically opposed from our real self is like trying to force yourself into shoes that don’t fit; you’re uncomfortable at best and the potential benefits are vastly outweighed by downsides.

When you’re trying to build the life you’ve always dreamed of, you need to do so in a way that’s harmonious with who you are at your core. You need to find the path that works for you4 , not for who you think you’re should be.

You’ll Take Anyone.

There’s nothing less appealing to a potential partner than feeling as though that they’re nothing more than a warm hole or body that’s filling a slot marked “girlfriend”. The more desperate you are to get what you want, whether it be sex or a relationship, the more likely it will slip through your fingers.

The metaphorical scent of desperation is the antithesis of attraction; much like negativity, it suffuses everything about you, from the way you speak to the way you act. It’s an ugly and unappealing. It screams of low self-esteem and equally low regard for the person on the receiving end of their attentions. After all, when you’re coming off as desperate, you’re telling the everyone around you that you don’t care for them as a person so much as what they represent: a featureless mannikin dressed up in entitlement and frustrated desire.

It can be tempting to rationalize this away: after all, why wouldn’t someone take being desired as a compliment? But then: when you say anyone will do, you’re saying that you don’t give a damn about the individual. They could be swapped out for the nearest stranger. Nobody likes feeling like an interchangeable, anonymous cog, easily replaceable and ultimately unmemorable.

On a practical level, desperation hurts you in a multitude of ways. You’re less likely to meet someone you would actually find success with as you blunder through looking for the first person to say “yes”. Even worse, your odds of turning a potential “yes” into a definite “no” skyrocket by pushing too far, too fast. Your desperation will cut you off from potential partners – the ones who would consider you will be turned off when they realize that any warm body will do and still more will assume that there must be a reason why you’ve been refused so often.

In short: your own desires are sabotaging your efforts to slake them.

As paradoxical as it may seem, you will never have better success at getting laid or finding a relationship by not desiring it.  Think of it as an exercise in zen: only in being desireless can our desires be fulfilled.

What is the sound of no hands fapping?

By being outcome independent – taking the focus off of finding sex – you are better able to relate to a potential partner as an individual rather than a walking, talking masturbation sleeve. You will be able to be in the moment and to appreciate women for who they are rather than what they represent. Your body language won’t tell her that you’re seeing validation through sex or that you’re measuring your self-worth whether or not you have a girlfriend.

The Tao of Steve had it right: you get laid more by not trying.

You’d Rather Argue Than Try

There will always be those who will say that they want to improve… but they’ll argue with every single suggestion or piece of advice they’re given. There’s always a reason why they already know that this, that or the other thing simply won’t work and that their initial belief is right.

To which my usual response is “how’s that working out for you?”

This tends to be classic ego-protecting behavior; we value being proven “correct” – and thus, sheltering our egos from the admission that perhaps we were wrong – even over getting what we supposedly want.

Yes, “we”. I used to be a classic example of this sticking point. No matter how badly I wanted to get better with women, I was steadfast in my belief that I was right all along and that it was the world that was wrong. Nevermind that I was the one looking for help in the first place;  I would argue and nitpick and try to catch anyone who would help me out in logical inconsistencies in order to prove the rightness of my position because I was right, dammit! 


Small wonder that it took me so long before I could make any progress. And no, it wasn’t working out terribly well for me.

I’m a fan of the (admittedly, medically inaccurate) saying: “the definition of insanity is doing the same thing over and over and expecting different results”. When the same behavior and efforts result in failure over and over again, it should be a signal that it’s time to try something different. There is value in trying a new approach – even if it feels as though it’s “not you” at first. Just because something is the way you’ve always done things doesn’t mean that it’s the right way.

“It’s not who I am” can be as much of a crutch as it can be an assist.

If an approach isn’t working, then it’s time to try something new and learn from the results… and then apply those results to your next attempt until you find one that actually works.

You Don’t Take Responsibility

This is a subject I’ve covered before, but it’s worth reiterating: you can’t improve until you’re willing to take ownership of your life. It’s entirely too easy to put up barriers and blame to shield yourself from responsibility. You’re not where you want to be because women are hypergamous and only want X type of men or because you’re beta or because this, that or this other thing… but it’s not your fault!

This attitude will always hold you back; until you can take ownership of your mistakes, you can’t make progress towards your successes.

Taking responsibility means removing negativity from your life. When you are able to admit your own involvement in your failures rather than finding excuses, you empower yourself to get better. You remove the pre-excuse for failure by removing “try” from your vocabulary.

“Said this before, I have. Listening this time, are you?”

You strip “can’t” from your internal dialogue. You may fail to do something. You may choose not to do something. But saying “you can’t” becomes another way of blocking yourself from making the attempt in the first place. I used to say that “I couldn’t” go up and talk to strange women, maybe get their number and a date… until I had to admit that I could, I just chose not to.

Until I was willing to take responsibility for my choice.

You Don’t Want It Badly Enough

Much like being desireless, this particular sticking point can seem paradoxical. Of course you want it badly enough! You wouldn’t be putting in all of this time and effort if you didn’t right?

But what, exactly, have you been doing? Have you been going out every weekend and trying to meet people? Have you been approaching as many people as possible? Have you been going out and making an effort to be more social at every opportunity? Have you been putting in the hours of self-reflection and study, trying to find your sticking points, break your bad habits and negative beliefs? Have you been swallowing down your fear of rejection, of humiliation and making a move even though you knew you didn’t have a 100% guarantee of success?

Or have you been doing a lot more reading and a lot less doing? Hours of research on the internet finding blogs like mine, lots of time spent talking about what you’re doing, dreaming of what your new life as a ladies’ man will be but less and less spent out practicing and taking the risks and making the sacrifices necessary to improve? Have you been finding any number of perfectly understandable reasons why you couldn’t approach the woman you had your eye on at the party? You couldn’t go out last weekend, you had too much to catch up at home. You may have only approached one woman last week, but you were tired!

The more excuses you make, more it becomes clear that you just don’t want it as badly as you think you do.

When it comes to achieving your goals, whether it’s getting better at dating, losing weight or even something like “writing that novel” or “travelling the world”, you will never actually accomplish them until you hit your tipping point. Until your goal moves from aspirational – “wouldn’t it be nice if I had/did this?”  – to necessity – “I need to do this”, you simply don’t want it enough.

Don’t get me wrong: success or failure isn’t an indicator of how badly you wanted it. This isn’t The Secret; the act of wanting something badly enough isn’t going to send out woo-woo vibes into the universe that guarantee you success and failure doesn’t mean you didn’t want it enough.

Wanting it – for whatever value of “it” you care to give –  badly enough means that you’re willing to do what it takes to get there, even if it’s going to take far longer than you’d prefer. You quit talking about writing that novel and start putting words down on paper; maybe not a lot, maybe just 400 words a day, but you do it consistently until one day… well, by God you’ve got yourself a 90,000 word novel sitting in front of you. You quit making surface changes or dieting and instead start making the lifestyle changes that lead to gradually losing weight and being able to maintain it. You start living on a ramen and miso soup diet while you sock away your money for that trip to Tokyo.

Or you start approaching 5 women every day, documenting your every interaction, gathering feedback and moving your way towards greater social proficiency.

I’ve never said that getting better at dating is easy or quick. It takes months, even years of effort and practice to break the habits and self-limiting beliefs of a lifetime. There’s a saying in PUA circles that I find apt: “The first 1000 rejections don’t count.” Until you’ve made those 1000 approaches and have gotten rejected 1000 times, you’re still a beginner, trying to learn the basics, the emotional equivalent of learning to crawl before you walk. It’s the same as making the free-throw a thousand times or practicing a single sword stroke over and over again until you’ve mastered it. You can’t sink the basket without having spent all those hours shooting and missing.

When you want it badly enough, you’ll be more than willing to rack up those thousand rejections – you’ll be ready to blast through those and a thousand more if that’s what it takes to get better. You’ll be willing to try new things, even if they seem strange or “not you”. You will be willing to go out, talk to people you never imagined you would ever approach in a hundred years even though you know that they may shoot you down. You’ll be willing to take the hits, endure the sting of rejection until you realize that rejections don’t actually hurt and you have more to learn from them than you ever realized.

And then – before you know it – you’ll realize you’re not being rejected the way you used to be. In fact, you’re starting to get more phone-numbers… and then more dates… than you thought you ever would a year ago, even a montago. You won’t be able to believe how frustrated you were, at how impossible it all seemed and how natural it all seems now.

All because you were willing to face your sticking points. Because you were willing to put in the time. You were willing to make the sacrifices and all the effort.

Because you finally wanted it badly enough.

  1. That’s still a thing, right? Tumblr’s like the new LiveJournal, ya? []
  2. although it definitely needed work []
  3. that is, the ones I’ve seen most often. This isn’t intended to be a comprehensive list. []
  4. please note very carefully that I said works. I will come back to this in a moment. There will be a quiz later. []