The Story of a Broken Arm, The State of Connecticut, and How I Learned to Approach Women

In the summer of 2008 I tore the ligament in my right elbow mountain biking in the White Mountains of New Hampshire. Devastated that I couldn’t work as a paramedic for six months, I reframed my thinking and realized I had been given the blessing of time. Since life is all about self-improvement, I decided to work on something that had always bothered me: my lack of success with women. This is when I came up with my first blog “90 Women in 30 Days.” The premise was simple: approach three women a day and document the results. Like most men in 2008, I had read Neil Strauss’ The Game and decided to test some of its lessons on the women of Connecticut. Here are the results:

Even though women will swear to their grave that the “bad boy” thing doesn’t work, it delivers results. The reason women don’t believe this, is because why would they logically accept that something negative like a “bad boy” works on them. They key there is the word “logically.” Women don’t process men logically, they process men based on emotion — how a man makes her feel. That’s why women are capable of falling in love with prison inmates or rappers that blatantly promote misogyny. Logically, it makes no sense to waste time and emotional resources on these men, but their attraction is governed by emotion. To be fair, it’s not specifically that they like “bad boys,” it’s that they like what this archetype represents: confidence and adventure. This is where older strategies like “negging” and “cocky-funny” fall in to play, because they represent those two qualities. Beautiful women — the only women men will to risk their egos to approach — are accustomed to the world at their feet, so if someone comes along and isn’t afraid of her, she’s going to raise a perfectly manicured eyebrow.

The way to capture a woman’s heart is you have to make her feel an emotion for you. With women, there’s a constantly evolving nebulous cloud of attributes that will get her attention, but the common denominators are that you have to make them feel a sense of security and danger at the same time. I realize that’s contradictory, but so are women. The “bad boy” is adept at making a woman feel secure through his confidence and adventure through his unpredictability.

If you’re a great hitter in baseball you have a .300 average, meaning when you step up to the plate, there’s a 30% chance you’re going to get a hit. Think about that: there are dozens of players in baseball that get paid millions and millions of dollars just to succeed 30% of the time. That same success rate applies to approaching women. If you think 30% is low, then that’s because you’ve never hit on women before. There are so many factors that go in to that 70% failure rate and many of them are beyond our control (e.g. her current mood, relationship status, a bad hair day etc.). Since much of love is timing, you have to strike at not only the right time (which we can’t control), but also with the right tools (which we can control). The only way you’re going to learn the right tools though, is by constantly practicing — trial and error and tweaking your home run swing. The caveat here is that women have an incredibly attuned bullshit detector; you can’t go for the shotgun effect and just fire away hoping to hit something. This means you should only talk to the women you truly want to talk to — be genuine. With this 70% rejection rate, you can’t take it personally, because sometimes the pitcher is (currently) out of your league, and sometimes the umpire just isn’t on your side. But the more you practice your stroke and the more swings you take, the more chance you’re going to get a hit.

The biggest take away I’ve learned from approaching women — which I’ve also applied to other aspects of my life — is to act without hesitation. Smart people are really good at making simple things complicated, and it’s easy to psych yourself out when you just want to have a simple conversation with a woman. I’m a chronic over-thinker that’s prone to micro-analyzing everything, so with women, I’d rather act impulsively and improvise as I go along. It’s the same thing with going for a personal record back squat or traveling to a foreign country, I don’t let myself do too much thinking — I just jump in the water. And when you do things like this you’re going to fail a lot, but if you learn from that, then you’ll keep failing better each time. When you see a woman you want to talk to then go for it, there is no “perfect moment,” but it’s better to have tried and failed, than to have never tried at all.

I would still call myself only above-average at approaching women, but since then, every girl I’ve met, I’ve attributed to the lessons I learned from that challenge. Being reckless, being consistent, and constantly evolving from failure, has not only helped me with women, it has also helped me with life. What I didn’t realize at the time is that my journey, was actually more about self-improvement then it was about women. A lot of men just want a magical pick-up line to attract the opposite sex, but we all know they don’t work, because there is no easy path in life to the things we value. The key is constant self-improvement, which as a byproduct, is going to yield more women coming your direction anyway.

Title Photo Credit: flickr