If you want to improve at dating, you need to quit looking at success stories. Instead, you need to study mistakes. You need to make more mistakes. Most people do.
In fact, that’s one of the biggest problems I see among young men. They’re afraid of mistakes. They’re afraid to fail. But mistakes are important… in fact, they may be the most important thing when it comes to learning how to date better.
See, you don’t learn much from success1. Success is great, but success rarely teaches you how to be successful. 9 times out of 10, studying someone else’s success just teaches you how they got successful. By focusing on success and being afraid to fail, you actually rob yourself of the ability to improve. You need to make mistakes in order to learn. Otherwise you run the risk of following in the footsteps of every wannabe and never-was. At best, you can follow the overnight sensation that fucked up their sophomore effort. One bright moment of glory and then disappearing into a puff of “what might have been”.
Making mistakes, on the other hand, can teach you what you need to do to succeed… as long as you know what you’re looking for.
What’s Wrong With Studying Success?
It seems counter-intuitive, doesn’t it? If you study somebody’s successes, model yourself after them, shouldn’t you be able to replicate at least some of their successes?
Not really. The only way that following in the exact footsteps of your Elan Musks or your Bill Gateses or even your Neil Strausses or the like will net you a similar success is if you actually manage to go back in time and take their place.
A person’s success tends to be contingent on a lot of factors, frequently things that you can’t account for. Trying to recreate World of Warcraft’s success – the Holy Grail of MMOs – is impossible because you have to have the exact confluence of events and timing that existed when Warcraft launched. It filled a very specific niche and created a new form of MMO experience; its imitators have since been trying to iterate on success that depends on a marketplace that no longer exists.
But just as importantly: focusing on those successes tends to blind you to all the failures. When you see a cranky old man in his late 90s smoking cigars and swilling bourbon, it’s tempting to say “well clearly tobacco and booze isn’t that bad” because hey, look at Grandpa Stereotype over there!
But you’re focusing on the one person who’s managed to live to a ripe old age despite his vices, not the mountain of corpses of people who didn’t. There are far more people who followed the same health regimen and dropped in their 50s when their livers fucked off for better working conditions. We talk about how they don’t make cars or movies or music like they did in whatever-year-you’re-nostalgic-for because we don’t have the failures any more. Everyone remembers “When Doves Cry” and “Against All Odds”; you’ll have to dig pretty damn deep to find anyone who remembers “Yo Yo Little Brother”. People still listen to Mariah Carey or Beck. Almost nobody remembers Rosco Martinez.2
The popular belief of “women love assholes” follows the same pattern. You see the assholes with girlfriends or wives (or both) and assume that being an asshole was a key part of their success. What you don’t see are all the people who got dumped for the exact same behavior, because they’re not dating anyone. The small number of successes stand out only because the failures go unnoticed.
This blindspot is known as the survivorship bias, and it gives us a false perception of reality. The fact that something worked doesn’t mean that it was the best. Many a stupid plan has been deemed brilliant after the fact because it worked despite itself.
Instead of looking at success, you need to look at failure to succeed. You need to focus on the mistakes.
Why Mistakes Are the Keys To Success
Focusing on mistakes can be difficult – especially when they’re yours. After all, most of our mistakes are painful reminders of times when we fucked up. Why would I want to, say, look back on the break-up that left me curled up in a ball for a year? What good is going to come from that?
Well, because examining that break-up would tell me exactly why it all fell apart. In this case, it was because I tried to push a relationship on someone who didn’t want one. Our relationship was never going to work because it was fundamentally flawed. I was just willing to ignore those flaws until it was too late.
But I ignored those mistakes… and that proceeded to sabotage my next relationship. And the one after that.
When we let our failures and mistakes fade into the ether, we make it harder to succeed. We lose track of the factors that make the difference between succeeding and failing. We start losing critical information – what caused this to fall apart? Why were we defeated? Why’d we get rejected?
When I started getting more adept with women, I used to focus like a laser on my successes. Whatever I did the night that I got a phone number or a kiss became my methodology for weeks. It didn’t quite hit the level of having to wear my lucky jacket… but it wasn’t far off either. Naturally, that success would be followed by failure after failure. It drove me crazy… I was doing everything exactly the same as I did before. Why the hell wasn’t I getting the same results?
Because I wasn’t succeeding, I was not failing, which is a very different thing entirely. The stars had aligned just right that night for me to pull off a Hail Mary and now I was trying to make the Hail Mary into my signature move. I was missing all kinds of critical information that guaranteed I was going to go down in flames.
One memorable3 moment came from a time when I’d thought I was doing well with a young woman I’d been flirting with. We ended up huddled up in a corner of the bar and making out. I didn’t hear from her later but, hey, make-outs right? That’s pretty damn good. That was a success, right? Except, it wasn’t. I hadn’t succeeded at all. I’d simply not failed, despite my best attempts. I was drunk, she was bored and willing to put up with my drunk ass because she had nothing better to do. I hadn’t seduced her with my wit and charm, I’d basically just annoyed her into it.
Focusing on my mistakes, on the other hand… well, it sucked. There were a lot of them. But paying attention to those mistakes, tracking them and categorizing them? That let me start seeing the patterns. I started noticing areas that I would trip up over constantly. I could see which mistakes were critical – the ones that would kill attraction – and which were survivable. The more mistakes I paid attention to, the more there was to learn.
Of course, the more I had to learn, the more I had to be willing to go out and fail.
Court Failure To Learn From Failure
One of the things that helped me get more comfortable with making mistakes was to study stand-up comedians.
Unlike most performers, comedians don’t have the luxury of working out their material in private. Musicians can practice scales and fingering and timing until they get it just right before having to perform in front of anyone else. Singers, actors… they can work in private with no audience or a very specific one. They can fine tune everything until it’s perfect.
Comedians, on the other hand, are dependent on an audience. You can’t develop comedy in a vacuum; they need an audience to in order to workshop their material. They have to go out and subject themselves to the immediate judgement of others to know whether a bit works or not. They may have struck gold on the first try, or the new joke may be elicit nothing but an awkward cough in the judgmental silence.
If a joke bombs, they have to go back and analyze just why it failed. Was it the delivery? Did they punch the wrong part of the story? Does it need to be edited down? Maybe it was just the right joke for the wrong audience.
To make matters worse, when the joke does bomb, they’re stuck on stage with everyone look at them. Now they’re in recovery mode. Can they win the audience back after they’ve fucked up? It takes practice and a quick wit to pull a dying set back from the brink. In fact, some comedians were known to go out and deliberately bomb in order to learn how to recover from those moments.
Now apply that attitude towards dating. Dating is inherently a multiplayer game; there’s no soloing a relationship.
You can theorize and strategize all you want, but at the end of the day, you’re going to have to work your material out – as it were – on a live audience. Whether you’re making a cold approach, meeting people through mutual friends or dating online, you’re going to have to put yourself out there. You’re going to have to test yourself and your game and see whether people respond.
And frankly, you’re going to have to accept that a lot of those will go nowhere. Sure, you can pray to get lucky and hit the bullseye on your first try, but the odds are against you.
You’re going to have to be willing to make mistakes. Lots of mistakes. The sooner you realize that mistakes happen, that they’re not fatal and that you can both recover from them and learn from them, the faster you will improve.
But you need to make sure you’re taking the right lessons away from those mistakes.
Making The Right Mistakes
One of the worst things you can do when you’re trying to improve your dating life is to go about it in a haphazard fashion. Randomly changing things up in hopes that you’ll stumble across your sticking points just wastes your time. More often than not, you’re going to just frustrate yourself – or worse, you’ll convince yourself there’s more wrong with you than there really is.
Instead, you need to take a methodical approach and try to narrow things down. One of the things I always tell people is to keep a dating journal – preferably a hand-written one. In this journal, you write down everything about your dating life. How many approaches did you make, how many worked? What did you say, what did they say, how did you feel?
But don’t just stick to your current efforts; you want to write down everything you can about your past relationships too. Failed approaches, relationships that didn’t work out, crushes that went nowhere, times you’d been ghosted… all of it.
When you’re writing these down, start asking yourself detailed questions. What was happening in the lead-up? When was the exact moment that they quit responding? When did you start getting the feeling that they were going to flake on you? What did you do in response? Did you get angry? Did you get needy? Did you plead or try to accommodate them?
In short: what are your mistakes?
Yeah, it can feel a little gutting to have all of your past failures laid out before you like that, but it’s important to power through that discomfort. You need to be able to face those mistakes and recognize there’s no shame in failing. The more data you have, the more you have to work with and the less likely you are to fail in the future.
It’s important to be as non-judgemental as possible as you write everything down. Listing reasons like “I’m just too ugly to date” are not only defeatist but unhelpful; it’s an excuse to not try. Instead, you want to focus on things you can change. “My face is too ugly” is a cop-out. “I need to work on my presentation,” or “I need to build on my uniqueness” on the other hand, is something you can do proactively.
After you’ve written down as much as you can, give it some time to settle before you go back to it. Take a break, do something completely unrelated and come back to it with a relaxed and refreshed brain. Then, read through what you’ve written with a separate notepad and start looking for patterns. Where do you lose the most ground? Exactly when do people stop responding? Are you able to start a conversation but have problems maintaining it? Are you able to make friends but not make a sexual connection? Do you panic at the first sign of waning interest?
These will help you figure out where to focus your energy. Not sure where to start? Not able to pull the signal out of all the noise? Here’re the most important parts of dating; start here and work outward.
But wherever you start, you need to put in the work. And that means you have to…
Give Yourself Permission To Make Mistakes
The key to learning from your mistakes is to experiment. You need to be willing to try new and different things – things that may well be outside your comfort zone.
Think of it as A/B testing; you use one approach with one person, then an entirely different one with someone else. Maybe one is your usual behavior, while the other is a more aggressive stance. How differently do people respond to that alternate take? Maybe you dress one way one night, then try a new look the next. Are people behaving differently? Are you feeling more or less confident? Use a different profile photo on Tinder. Rewrite your bio on OKCupid. Try an entirely out-of-character email on Match or Plenty of Fish.
In short: try to make new mistakes.
Yeah, you’re going to fail. You may well fail a lot. And that’s fine. You don’t need to do everything perfectly. Hell, you don’t even need to succeed. You just need to learn… but you can’t learn without taking some risks. The more comfortable you get with not being perfect and taking chances, the more you can learn.
Make mistakes – make the right mistakes – and learn from them. You may fail, but those failures are going to be what brings you your ultimate success.