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Stop Playing it Safe With Women

How many women dislike you on dates?

Odd question isn’t it.

But wait, Ed!

Isn’t the whole point of dates to get someone to LIKE you?


But I promise you’ll get more people liking you if you have more people disliking you.

People pleaser

Growing up I was the polite guy. I didn’t push my agenda and was always the one sitting quietly in the background.

I went out of my way to please everyone.

Everyone except myself.

I would do all this, not because I wanted to be nice, but because of a desire to be liked. It was a protection mechanism to prevent affection and love (something humans crave) being withdrawn.

When interacting with women:

  • I couldn’t decide on a date venue and would ask her where she wanted to go
  • I wouldn’t pick a restaurant in case she didn’t like it
  • I would agree with her about everything
  • I would re-arrange my schedule to accommodate her requests
  • I would travel to meet her despite it being out of my way
  • I would watch the films she wanted to watch
  • I would hesitate to kiss her on date in case she pulled away
  • I wouldn’t invite her back to my home in case she thought I was moving too fast

Meanwhile the guys who didn’t seem to care were extremely successful.

They moved through life as they pleased, saying what came into their head with little filtering, pissing people off, being rude, having a lot of fun, and enjoying life. They often had many friends and were the life and soul of the party.

They also attracted a lot of women.

The polarisation effect

man holding compass

The best politicians, musicians, celebrities and film stars are polarising. They are worshiped by some and vilified by others. And they don’t mind, because they have their core set of fans who will love them forever.

You will have far more success on dates and life in general if you polarise people.

Once I realised this I stopped trying to be liked. I didn’t need EVERYONE to like me. I just needed a few people. Be that friends, family or women I was romantically interested in.

People want to see your fire, your mystery, your passion, your drive, your anger, your idiosyncrasies, your faux-pas.

Those things make you interesting. They make you unique. They make you, you.

The real you.

Pushing it


When dating you must hold two opposing thoughts in your head simultaneously.

On one hand you need to be outcome independent. You can’t worry about how the date is going, if she likes you, or whether you’ll get another date. The more in your head you are, the more filtered you are likely to be, and the more likely you are to put up your protection mechanisms and play it safe.

At the same time, you must be aware of what you want to achieve. If you’ve just met a woman then the goal is to get her phone number. If you’ve got her phone number then the goal is to ask her on a first date. You’ve had a good first date, and now your goal is to have a second date.

And so on.

Once you know your goal, you work towards it. Effort is required. You have to push forward whenever you can.

Sometimes you won’t want to because there’s a risk you’ll lose everything.

Think of the game show Who Wants to Be a Millionaire. As the game progresses the contestant accumulates money for every question they answer correctly. At any stage the player can walk away with the money, or risk it all to win double.

Dating is the same, except there is no option to walk away with what you’ve already won.

You must either progress or lose her forever.

What tends to happen is you get to a specific level and can’t progress because you fear losing. It’s no good getting to go on a second date and then telling yourself ‘This is good enough. I don’t want to rock the boat in case she goes off me, so I’m not going to kiss her even though I want to and am pretty sure she wants me to’.

You must progress or fail. Those are the only two choices. By hesitating to progress you increase your chances of failing.

There have been so many occasions where I could have got a first date if only I’d asked the woman I was chatting to for her phone number.

But I played it safe.

There have been times I could have kissed a girl on a date if only I’d tried.

But I played it safe.

There have been times I wanted to sleep with a woman and she wanted to sleep with me, but I hesitated and played it safe.

By not playing it safe you will be rejected more and succeed more.

Going too far

Don’t read this article and think I’m advocating being aggressive, rude or pushy towards woman. Those traits may be the opposite of a nice guy, but the intent behind them is still attention.

I’m not advocated acting mean or disrespectful to your date. I’m simply saying if a risqué thought comes into your head which you find hilarious, say it. If you don’t like cats and she adores them, don’t lie and pretend you do just to win her over.

This is about freeing you up, and giving you the courage to act authentically in the dating arena.

It’s about making you comfortable revealing your masculinity, your desire to be loved, your desire to have sex with beautiful woman, your desire to lead, your desire to take on the world and achieve great things in you business and personal life. And doing so in a way that is congruent to you.

The aim is to let your true, unfiltered personality shine. Then sit back and let the other person decide if you are right for them.

Don’t be a forgettable date. Be the guy she goes home swooning over, or the guy she felt the passion of, but who wasn’t right for her. Either of these are better than the guy she shrugs her shoulders about and says ‘He was alright’.

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