The Worst Dating Advice In the World (and Why It Really Works)

Worst Dating Advice and that Works?


There are a number of cliches when it comes to dating advice out there, each of them hollow and infuriating.

But none of them are quite as mystifying as the perennial classic: “The best way to find a girlfriend is to not want one so badly.”

“Don’t try so hard and it’ll happen.” “You’ll only find a relationship if you aren’t looking so hard…”

It’s gets tossed out almost as often as “Just be yourself” and is about as useful, but with the added benefit of borrowed authority and meaning by sounding like a zen koan delivered by an ancient master. “Meditate on this truth and you will understand the path of the Player, grasshopper.”

More often than not, this is the advice handed out by someone who believes in the binary state of dating skills – you’re either good or you’re not. It’s advice hinged on the idea that dating should be effortless and that attraction is magical and you can’t actually create it; your dating future is in the hands of fate, so there’s nothing you can really do to force the issue.

Thing is though – and you had to know by now that a twist was coming – they’re not entirely wrong.

The idea – that your best success comes with less effort – is sound. The issue is that most people misunderstand why this is true.

Why We Get It Wrong

The big misinterpretation of “Don’t try so hard” is the idea that you’re being told “Let go and let God” – that is, quit trying to make it happen yourself and let fate take care of you. Instead, the real idea behind it is closer to the Taoist idea of wu wei – “action without action”. Trees don’t try to grow. They just grow. Similarly, the idea behind “Don’t try so hard and it will happen when you least expect it” is “don’t try to find a girlfriend, just find a girlfriend”. 

To put it in a more easily digestible nerd form: you don’t control the Force, you let the Force flow through you. Just as you don’t try to find someone to sleep with, you live your life in such a way that people come into it naturally – including people that will want to have sex with you.

As I’ve said before, it’s the illusion of luck or fate; it’s not that the Gods have suddenly decided to smile upon you and bless you with someone who really wants to see your boner, it’s that you’ve set yourself up in such a way that these people come into your life without forcing the issue – and when they do, you’re in a position to actually act upon the opportunity.

But while it’s easy to say “go with the flow”, let’s look at some of the reasons why trying can actually make things harder for you.

1) You Want The Wrong Things

We’re less than a week away from Christmas, and less than two weeks from New Year’s, and it’s only natural for people to look at their lives right now and resent the fact that they’re single. They’re tired of being lonely, tired of looking around and feeling like they’re the last person in the world without their own little snuggle bunny. They want nothing more than to find a relationship  and they want it now.

And yet they don’t understand wy the harder they try to find one, the more it seems to slip from their grasp.

The problem is that they’re looking for something that they are confusing something that they want – a relationship – for something that they need – validation. They’ve convinced themselves that this one magic bullet is going to complete them, make them feel as though they’re no longer missing that piece in their life and now they’re whole. It’s that desire that’s fucking them over. By seeking an external solution for an internal problem, they’re trying to apply a bandage to a sucking chest wound – it might make it suck a little less for a little while, but it’s not going to fix the real problem.

You don’t want to know how long it took me to learn this issue myself.

Someone who is trying to have his emotional issues fixed by another person isn’t going to be the most confident or outcome-independent person; they’re going to be fixated on the solution to their imagined problems.

They’re treating another person as a thing, an object, a shape that can fit into the cutout marked “relationship” with the expectation that it will magically make things better. They want a girlfriend who will drag them out of their shells or make them more interesting people. They want more sex because it “proves” they’re attractive or that they’re not “losers”. They want the life that they think has been denied to them and that other person is going to be the gateway to finally fulfilling all of their hopes and dreams. You can’t fill the hole in your life with a person any more than you can with sex, drugs or possessions. 

Not even if it's really cool stuff?

This is not an attractive trait in a person, and other people can pick up on this belief very quickly… and it’s going to repel them.

It’s one of the oldest cliches out there, but you really can’t  make a relationship work if you aren’t happy with yourself. Taking time off from trying to get laid or finding a relationship in order to get your own life in order will make it much easier in the long run. A proper partner-in-crime is a compliment to an awesome life, not a prerequisite. Build a life you’re happy with and find what you need to complete yourself inside and you will discover that everything comes much more easily.

2) You’re Trying Too Hard

Yes, I know how much I’ve emphasized that getting better at dating requires a lot of hard work, and the idea that you’re trying too hard seems contradictory.

Sometimes when you’re focused on a task, it’s possible to get tunnel vision and lose your focus. You become obsessed with the minutia and repetition and lose track of the bigger picture.

How many times have you been playing a particularly frustrating video game – especially an old-school, Nintendo-hard ((I’m sorry, I’m so very, very sorry…)) game like Ninja Gaiden – and you’ve been stuck on one. Fucking. SPOTIt might be the boss that kills you with a cheap one-shot kill attack every time. It might be trying to sneak through a mandatory stealth section when you can’t avoid detection no matter what you do. It might be trying to thread the needle on a tricky platforming section that kills you every goddamn time.  

This alone is enough to send people of a certain age into a frothing rage.

You reload, replay, die, scream, reload, replay, die. Wash, rinse, repeat until you’re about to snap your controller in two. You might make a little progress only to die again and end up back where you were before… and now it seems almost random as to whether you can make it that far again. Your world narrows until nothing exists except trying to beat that section.

And then you stop. Take a deep breath and take a step back. You put it down for a few hours or overnight, come back to it fresh… and all of the sudden you blaze through that section as though it were nothing.

It can be almost any task – a painting you can’t get quite right, a section of a writing project that you’ve deleted and re-written twenty times, trying to master a three-point free-throw… or dating.

Just as your frustration with a game can inhibit your ability to play it, being too determined to get a date or get laid can inhibit your ability to let your charm flow through you. Your aggravation leaves you tense and annoyed – not only does this bleed through to your interactions with other people, but it can also leave you focused on all the wrong areas. You might be absolutely determined to go out and meet someone via cold-approach that night, but your attention is entirely on making approaches and as a result, your body language and tonality is completely off.

Think of it as trying to perform a waltz with every muscle in your body tensed at the same time. You may want it more than anything else in the world, but your own body is going to fight you every step of the way and make it harder than before, slowing you down, making you expend more and more energy and tripping you up.

Now imagine that same waltz after all of your muscles have relaxed. Suddenly what took all of your concentration and energy feels almost effortless, as though you weigh nothing at all. You glide, instead of stomping; you move with grace and poise instead shuddering and shaking as you push yourself through the steps.

Instead of focusing on one aspect – getting a boyfriend or girlfriend – take a step back and just focus on being social. Having no agenda outside of enjoying yourself and the company of others makes it much easier to let your best self shine through, rather than circling the room like a shark, looking for potential targets.

On a similar note:

3) You’re Too Focused On Results

The idea of “outcome independence” is a popular one in the dating advice world, and with good reason. By letting go of a focus on the end result – a pile of clothes at the foot of your bed, the two of you coated in the sweat of your efforts, staring at the ceiling, unable to stop grinning as you bask in the afterglow – you are freed from the hang-ups and sticking points that can trip you up.

When you let yourself get too hung up on a specific goal or a specific person, you start to give it greater levels of importance in your mind than it really deserves – and with it comes greater levels of pressure which ups the possibility that you’re going to choke in the middle, panic if things go even slightly wrong or, for that matter, psyche yourself out entirely.

Back in the early days of my transformation, I was so absorbed in the potential outcome of every interaction with women that I would have mini panic-attacks while I was talking to them. It became a question of “Can I actually manage to keep this routine going when I’m fairly certain my heart is going to explode? OH DEAR GOD DON’T LET HER REALIZE I THINK I’M ABOUT TO DIE RIGHT NOW.”

This reached it’s peak when in the course of one night, not only did I literally choke on making the approach, another time I actually threw up from self-inflicted nerves. While I was talking to a woman about why I became an artist.

"I don't think you're gonna recover from that one, buddy."

By focusing so much on the idea that I had to impress this woman right here, right now, I put an insane amount of pressure on myself. It was as though I was being called up to hit the tie breaker that would win the World Series… after having just warmed the bench for the last 25 years.

My big breakthrough came when I quit treating every woman I approached as someone I had to succeed with, whether I was defining “success” as “said hello”, “got her number” or “got her in bed”. Making the mental switch that it didn’t  matter whether I impressed her with my wit and charm or if it even went anywhere beyond a pleasant 5 minute conversation with a stranger felt like taking off a thirty pound weight vest. I didn’t  feel any self-induced pressure to make things happen; instead, I was relaxed and at ease and able to be in the moment rather than weighing everything and judging myself based upon my success or failure. The fact that I was so much more calm and chill read as confidence and I was no longer intimidated by the people I was speaking to.

And I started to have greater levels of success.

Being able to separate yourself from the outcome – to just treat each interaction with a person as that interaction, without worrying about your agenda or trying to impress them, seduce them or otherwise work towards a goal – will take away much of your anxiety and nervousness. If you don’t get her number… so what? It doesn’t matter  – that wasn’t  the point and you’re the same awesome person you were beforehand. There will be others, and you can enjoy spending time with them as well.

4) You Are Not Ready

This can be a tough one at times.

It is all too possible to let your ambition outrace your ability to match it. It’s only natural; we all want results – especially when it comes to our dating lives – and we all want them right the fuck now. It’s a part of the human condition, and if you’re like I was, you’ve been feeling this frustration for years if not decades and you want to make up for all that lost time… starting right this goddamn instant.

But like Luke rushing off to face Darth Vader before he completed his training, by going out and trying to force dating success to happen, you’re setting yourself up for failure and defeat – which can, in turn, set you even farther back than you were before.

It’s a common issue with people who’ve started working on improving their lives – they want to believe they’re further along than they really are because we want to get to that end result where all of our dreams come true. But because we’re in a rush… we fuck up. We trip over things that would never have phased us if we had spent a little more time practicing and preparing ourselves. We make rookie mistakes. We imbue things with too much importance before we’ve gained the experience and wisdom to realize how ephemeral they are.

And to make matters worse – you can find the right person at precisely the wrong time. There’s nothing more heartbreaking than a relationship with someone who you know is right for you, but the timing was wrong or that you weren’t in a position to actually make things work out… and the realization that you could have, if you hadn’t tried to force the issue and were willing to wait just a little longer.

Some things do need to happen in their own time. Not in the woo-woo sense, but in the sense that sometimes just because we want something doesn’t mean that we’re ready to have it… but we will be in the future.

I should know.

I’ve rushed into relationships with women – awesome women, women with whom I’m still friends today – because I thought I was ready when I wasn’t. I thought I had to get in and lock them down now because if I didn’t, I’d miss my chance… and in doing so, I doomed those relationships. I still had a lot of learning and growing to do before I was ready to pursue them.

By being willing to wait and – to continue abusing the Jedi metaphor – complete my training meant that when the time did come, I would be ready.

And it’s a good thing I did. There was one person in my life who – at the right time and in the right place – would be my ideal partner. If I tried to make it happen before I was the person I needed to be, it would have fallen apart.

But by waiting, growing and biding my time, I was able to be exactly who I needed to be and where I needed to be in my life to make it happen.

And it did.

I’ll have to tell you about it some time.

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