You've probably heard of terms like 'fail faster' and 'fail forward.' The basic gist is that you learn from your mistakes. The only way to actually improve in the real world is by taking action. Inevitably you'll make mistakes. It's your relationship to making mistakes that will ultimately determine how long it takes for you to 'succeed.' Let's give an arbitrary definition of 'success': attracting a woman and getting intimate with her.

How many cold approach interactions do you need to have in order to even feel comfortable flirting? To no longer be nervous? 100 approaches is sometimes touted as the number by some guys. Some say 1000. Assigning a number to yourself, based on others' experiences (their rough estimates) is a bit of a fool's errand. Let's explore why.

Reference experiences desensitize you to the activity of approaching and opening women. There's no doubt about that. A wise man once said that the brain needs proof, not promises. Every time you talk to a cute woman and things go OK (she doesn't throw cake in your face), you give yourself proof. A brick is placed in the wall of self-confidence that you're building up.

It's important to acknowledge milestones when it comes to progress. Progress doesn't happen over night, as teachers have told you since childhood. However, fixation upon the end goal of progress comes with a set of problems. Let's assume that the end goal is to attract a woman and get intimate. That's what most guys want when starting out. Achieving this goal is not something that provides permanent happiness and a nirvana-like state. You won't become an enlightened Buddhist by doing what nature intended.

This being the case, you have to learn to enjoy the process of meeting women. The process of meeting women makes up a large bulk of time. It's time that must necessarily be spent in order to attract and be intimate with attractive women. The end goal moment itself may not necessarily last that long. Saying hi and getting a splash of female energy back should be fun. You can choose to see it this way. You can experience this as regularly as you're prepared to approach.

You can re-frame. You can become process-driven. There should always be a desire to achieve an end result. You should have fire in the belly. That's having full intent. However you can, simultaneously, have freedom from the final outcome: the 'end goal.'

There's a clear paradox regarding the way you have to relate to what you're doing. If you're not having fun, you won't get results. You may initially see it as if you're not getting results, it's not fun. This ego involvement will massively mess up the journey unnecessarily, when nothing was ever a big deal to begin with (as you'll find out). Really, caring too much is the opposite of what women find attractive. It sends all the wrong signals. A woman may think, "this guy doesn't get dates, because if he did, he wouldn't be this needy" (and serious).

How do you begin to solve this issue? Start by taking some of the focus off yourself and try to engage women with empathy. Do this in a way that adds value and good vibes, and isn't a quest to extract value (think creepy Golam's quest for the ring in LOTR).

Think about why women go to bars and clubs. It's to have fun, isn't it? Give them a similar experience in everyday situations. Put simply, when a man playfully teases and challenges a woman, it is fun for her. If you're so nervous that you can't do this, then you'll have to fake it until you make it. Take one small step at a time. Say hello. Say hello and smile the next time. Then say hello and smile, and make an observation. Then do all of this, but make the observation playful and tease a little. Make gradual improvement. Enjoy basking in female energy. Forget about the number of approaches (and her phone number for that matter – aka 'my precious').

You will get more and more desensitised by flirting consistently. It's similar to scuba diving. There will be a little discomfort mixed with excitement in the beginning, then the excitement will take over. Reference experiences and muscle memory ensure this. Competence leads to confidence. You can create an upward spiral.

You have to proactively think about the way you relate to this issue. "I need to have minimum 100 interactions" will become "I need to have minimum 1000 interactions" if you're making it torture for yourself. The last thing you want to do is see it as a case of just trying to get through interactions to get to the other side (nirvana, they say?).