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How Men Can Become More Confident and Successful in Asking Out Women

This is an excerpt from The Masculinist Newsletter #4.

My first set of practical improvement tips help with building the social confidence necessary to meet women.  This is valuable on multiple levels.  On the one hand, women are attracted to confident men. On the other, you actually have to have enough confidence to approach a woman and start talking to her before you can even think about asking her out on a date.

Let’s be honest, this can be intimidating. Virtually all dudes have some level of anxiety and fear of rejection when approaching women. This is one of the riskiest things you can do from a self-worth perspective. Getting the door slammed in your face is hard enough when doing cold call sales. But at least then you can console yourself that it’s not personal. But with women, it’s very difficult to not see it as personal. After all, the product in question is you. Our brains are very good at spinning out disaster scenarios of being humiliated by rejection – especially if it’s someone in our social circle, such as a church, where we assume everyone will find out we got shot down in flames. No surprise, men too often exhibit the passivity and apathy that pastors are frustrated with. They aren’t confident enough to overcome their fear of rejection.

I can’t solve all your problems with this today, but I can share two techniques I personally used that helped me gain confidence with women.

The first will help you improve your eye contact. Good, strong eye contact is critical not just in meeting girls but in every relationship, so this one can really pay dividends.

I’m a very introverted guy who traditionally scored pretty high on the geek scale. I used to be a computer programmer, which should give you an idea. I was very bad at making eye contact. My social awkwardness was so bad at one point that my boss sent me off to charm school, aka executive coaching. Here is a snippet of the feedback I got from senior colleagues (collected anonymously).

There’s something about his head. He never really looks at you, and that puts people off. It creates unease….Aaron should lift up his face and look straight on at people. He’s got a nice face but it looks at you through the tops of his eyes with his face down. Maybe he’s shy or something. That’s off-putting.

That – and much more besides I can assure you – was not pleasant to receive, but super valuable. Everybody’s got a rap sheet. The only question is whether or not we know what’s on ours.

I improved my ability to make eye contact through a simple exercise I still do today. Everywhere I go I scan the people around me and try to make eye contact with them, whether that be walking down the street, riding the subway, or shopping in a store.  In NYC people tend to studiously avoid eye contact, but I’m still often able to pull this off.

So try that exercise. Get in the habit of trying to make eye contact with the people who come within range. And here’s the key: don’t avert your eyes when they notice and establish eye contact with you. Hold it 2-3 seconds before breaking eye contact. This isn’t easy – or at least it didn’t come naturally to me.

I never played football, but I’ve read that one reason players practice hitting a blocking sled is to train themselves to make full force contact with opposing players without pulling back or flinching, which is our instinctual reaction. I see this eye contract drill as sort of like practice hitting a blocking sled. The idea is to make it second nature to be able to establish and maintain strong eye contact, by repeatedly doing it in a low risk, “practice” setting.

The second drill is to take the next step and make a habit of striking up conversations with people.  I’m less obsessive on this than on eye contact, but I’m always looking for ways to initiate brief remarks to someone. There are plenty of settings where this is very appropriate to do, such as with a clerk who is ringing you up in the story. Or just say something to the person next to you in line. Or compliment someone on the train who is wearing a particularly cool piece of clothing.  Or make a comment to someone about his dog.

Don’t try to force someone into a long conversation. Just a couple of sentences will do. Talk to everybody – male and female, young and old (though never talk to minors unless their parents are present).  Don’t worry about impressing them or even thinking about asking any of them out.  The point is simply to build the social confidence to initiate a conversation with a stranger or someone you don’t know well.  This can be awkward, but if you can’t even exchange a few pleasantries with a store clerk, how you ever going to ask a woman out?

These are just two simple and easy ways for shy or timid guys to start building social confidence – something that will pay dividends far beyond the dating world. Once you get to the point where you’re able to make strong, unapologetic eye contact, walk up to a woman, and initiate a conversation, you’ve taken the first step.

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