Sometimes, I think back to how dumb I used to be and it makes me cringe.

Back in high school, I used to have a crush on my locker buddy, Olivia. We only had a couple of classes together all throughout high school, but every morning before classes began and every afternoon when we left school at around 3:15 pm we would meet up at our lockers and shoot the breeze for a few minutes. I always looked forward to that.

Honestly, I don’t remember what most of our talks were even about. I guess that’s the thing about memories. Those small details tend to fade away after a while. I no longer remember what we used to talk about or what she wore or even what my own locker combination was. If I went back to my old high school and look at it today, it would probably be much different than how I remember it.

Details fade away, but you remember 1) the people who were there and 2) the way they made you feel. Maybe that’s what really matters.

A few years after high school I thought I would look up Olivia and ask her out. Here’s where my capacity for doing dumb things kicks in. I sent her a message over FB asking if she wanted to meet up. A few days passed and I didn’t get a response. Instead of doing the rational thing and realizing that she’s either too busy to respond or simply not interested in meeting up, I tried to play it cool. I sent her another message along the lines of,

“No response? Fine! I don’t care that much anyway.”

This brings me to what I want to talk today, how most pickup and other dating advice tend to get confidence wrong. Because it hurts a little when I remember my own lame attempts at being “confident”, but it hurts A LOT when I see other people telling men to do the exact same thing!

Let’s talk about how pickup gets confidence wrong.

You can’t cover up neediness by pretending to be confident

Mark Manson writes in Models that a man’s attractiveness tends to be inversely related to how needy he is. Your level of neediness comes out in the way you carry yourself—how you talk to her, your attitudes, your posture, your tone of voice, etc. The more needy you are, the less attractive everyone else tends to find you. Even if you don’t consciously realize it.

That’s what most pickup advice misses. They’ll tell you to act indifferent. Hold frame. Be stoic. Pretend that you care less about her than you actually do. Mark Manson calls this “performance”, because you’re just putting on a show and acting like you’re less needy than you really are.

Does “performance” actually work? It “works” in that you might be able to get a woman to stay with you in the short term. But after that you’ll begin to wonder why all of your relationships feel so unfulfilling. By putting on a show instead of working at the actual root neediness, you deprive yourself of the warmth and the secure, trusting bond that comes with a healthy relationship.

On “playing the numbers game”

Here’s another confidence strategy that I’ve seen talked about. “Playing the numbers game”. You just approach 50 or so women until the fear of rejection goes away, and the Law of Averages says that some of them are bound to go out with you. It sounds good in theory, but this strategy misses a few key things.

The biggest problem with the numbers game is that it fails to address the same underlying issues that “performance” does. If you’re coming from a place of neediness then it doesn’t matter how many women you approach. You could ask out 10, 50, or even 100  women and that neediness is still not going to go away.

In addition, by playing the numbers game you’re no longer approaching women because you’re genuinely interested in her. She’ll sense that, which stacks the odds against you. If she’s just looking for a casual fling, then you’ll possibly get a few hookups this way. However, most women who are looking for a relationship will probably just turn you down. If you’re coming from a place of neediness, this can grate on you and make you feel even more insecure, which in turn makes you even less likely to find someone to go out with. It becomes a vicious cycle.

Also, I’ve encountered over 50 spiders in my lifetime and they still scare the living daylights out of me. Just saying.

The numbers game can work if you’re already coming from a secure place and just need a little motivation to get out there and start talking to women. However, if you’re coming from a place of neediness then you’re not going to be magically cured by approaching X number of women.

True Confidence

How do you become confident, then?

One of the very best descriptions of confidence that I’ve ever seen comes from the book Mate by Tucker Max. He writes, “Confidence is the realistic expectation you have of being successful at something, given (a) your competence at it and (b) the risk involved in doing it.” When you positively influence these two factors, it naturally makes you more confident.

The way to lower (b) the risk involved in doing it is actually so boring that few people talk about it. You fill your life with fulfilling hobbies. With good friends. With a job that makes you excited to get out of bed in the morning. Fill your cup of life and make sure you’re not putting her on a pedestal.

When you have a fulfilling hobby, job, and or social/group to fall back on, you’re going to be okay even if you get rejected. This makes you less needy and more confident.

Once you have that down, you can increase (a) your competence at it. Practice talking to people and come up with a few interesting stories to share with her.

Looking back and moving ahead

Olivia still talks to me as a friend, which is surprising given how dumb I used to be back then. I’m not sure whether she’s forgotten my awkward attempt to ask her out or if she just pretends not to remember…but I really hope she forgot.

Part of me wonders why I bother doing this to myself. Why revisit these memories? Why not just leave it buried forever with all the other repressed stuff from my teen years? I guess it’s therapeutic. Writing it all down. Taking the bad stuff and putting it out there on paper. It’s better than keeping it inside, I think.

The other day I asked Olivia if she wanted to meet up again for old times’ sake. As a friend. I said that I’d be in town for a few days and that I’d enjoy catching up again, but if she was too busy then that would be okay too.

And this time, I meant it when I said that either way I’d be okay.