Article

Why Am I Confident in Other Areas but Terrified of Approaching Women?

10 min read

Almost every straight man has experienced some version of this:

You know you're competent in one or two areas of your life. Maybe you're good at your job. Maybe you're athletic. Maybe you're funny. Maybe you're a great musician, gamer, artist, or whatever else you genuinely enjoy.

Then you see a woman you're attracted to in public, and suddenly you're scared shitless to say hello.

What the hell happened to all that confidence?

You haven't lost your confidence. You're stepping into a skill you've barely practiced.

Confidence Is Specific to the Skill

Think about something you're already good at. You're alive, which means there is almost certainly something that interests you enough to spend hours doing. Maybe it's drawing, dancing, singing, lifting weights, reading, skateboarding, playing video games, or playing sports. Everyone has something.

And if you've spent years doing something you genuinely enjoy, you're probably pretty damn good at it.

Even the guy who spends hours playing video games can look at his stats and know exactly where he stands. He might have an excellent win rate, K/D ratio, ranking, or whatever metric matters in that game.

At the same time, that exact same guy might be completely incompetent at something else.

That's normal. It's part of everyday life.

I'm a perfect example. My handwriting is terrible, and I have essentially zero interest in drawing. Put me on a baseball diamond, volleyball court, basketball court, or padel court, and I'll be right at home. I've spent years playing sports because I actually enjoy them. The movements, teamwork, decision-making, competition, and pressure are natural to me.

But put a pencil in my hand and tell me to draw something?

Get ready for a disaster.

I haven't seriously drawn anything since I was forced to in grade school. Art class was a special kind of torture. If someone put a gun to my head and said, “Draw this picture perfectly,” I wouldn't suddenly unlock some hidden artistic ability. I've spent almost no time developing that skill. So how could I possibly expect myself to produce world-class artwork?

Hell, I'd be happy if it remotely resembled what I was supposed to draw. And if the colors even stayed in the lines, I'd consider it a win.

And yet men routinely expect themselves to do exactly this with women. They've never approached a woman they found attractive in public, learned how to start a conversation with a stranger, practiced handling awkwardness, experienced dozens or hundreds of different reactions, or learned how to recognize interest, disinterest, or when to leave.

Then they see an attractive woman and expect themselves to suddenly execute perfectly.

Why?

Women aren't a magically different species of human. Talking to an attractive stranger is simply a skill you've probably never developed.

The Stakes Feel Bigger Than They Are

Think about shooting a basketball. If you've never picked up a basketball in your life, I'm not going to put you on the free-throw line and expect you to make ten shots in a row. You might hit the backboard six times. You might airball the other four. You might not even know how to hold the fucking ball correctly.

And nobody would look at you and say, “Wow. You must have some serious confidence issues.” They'd say, “Well... he's never played basketball.”

BINGO.

Now imagine taking those same ten free throws while you're completely alone in an empty gym. Pretty low stakes, right? Miss? Who cares? You pick up the ball and shoot again.

Now put 20,000 people in the arena. Put cameras on you. Put your free throws on national television. Tell everyone watching that if you miss, they're going to know you missed.

Suddenly those same ten shots feel very different.

Your ability didn't suddenly disappear. The perceived stakes changed.

That's a huge part of what happens when you approach a woman you're attracted to. Your rational brain understands that you're simply walking over to another human being and saying hello. But another part of your brain doesn't experience it that way. It sees an attractive woman, recognizes that the interaction could involve rejection and social judgment, and starts screaming:

“THIS IS IMPORTANT. DON'T FUCK THIS UP.”

Historically, social belonging was crucial. Humans evolved in groups and depended on other people for safety, resources, cooperation, and survival. Being rejected or excluded by your social group could mean death. We don't live in that world anymore.

If a woman in a coffee shop doesn't like your approach, you're not getting kicked out of the tribe and thrown into a local volcano.

But your nervous system doesn't have a little notification pop up saying, “Don't worry, Phil. It's 2026. There are 8 billion people and you'll be completely fine.”

It reacts to the perceived threat. So the interaction can feel dramatically more important than it actually is.

That's why you can be completely comfortable competing in a sport, giving a presentation at work, or doing something you've practiced hundreds of times—and suddenly become terrified of walking twenty feet toward a woman.

It's not necessarily because you're secretly insecure. It's not because you're incapable of confidence. And it doesn't mean there's something fundamentally wrong with you.

You're inexperienced at a skill that your brain has decided is extremely high-stakes.

Confidence Comes From Experience

There's only one real way to change that.

Practice.

Want to get better at dancing? You have to dance. Want to get better at basketball? You have to shoot the ball. Want to get better at Modern Warfare 2? You're going to have to play Modern Warfare 2. Watching someone else play isn't going to give your hands the repetitions.

And wanting to approach women isn't enough either. Eventually, you have to approach women even with your brain actively working against you.

You can't think your way into becoming comfortable with something you've never done. You can't watch another 100 videos and expect your nervous system to suddenly say, “Alright, boys. We've completed the YouTube curriculum. We're ready.”

At some point, you have to take the shot.

And your first shot might be fucking terrible.

Guess what? That's okay.

Maybe your voice shakes. Mine certainly did. Maybe you stumble over your words. Maybe the conversation lasts thirty seconds. Maybe she isn't interested. Maybe you walk away thinking you looked like an idiot. Maybe you get her number.

So what?

You just took a shot. And you lived to tell the tale.

The next one might be slightly better. Then another. Then another.

Eventually, you start collecting something you didn't have before: data.

You learn what actually happens when you approach. You learn that some women are interested and some aren't. You learn that awkward moments don't kill you. You even start laughing at some of them. You learn that rejection is survivable, how to start conversations, how to read situations, and how to handle yourself when things don't go perfectly.

Every single one of those experiences gives your brain another piece of evidence:

I approached her.
My voice shook.
I stumbled over my words.
She wasn't interested.
And I'm still standing.

That's data.

Eventually, the thing that once felt like walking onto national television starts feeling more like walking into an empty gym. You're not walking toward that woman with zero information anymore. You've got repetitions. You've got experience. You've got evidence. You've got a database. You've accumulated data.

Maybe that's a better way to think about confidence.

Confidence: accumulated data.

Not all confidence, obviously. But a huge amount of what looks like confidence from the outside is simply someone who has done the thing enough times that their brain no longer treats it like an unknown.

Think about someone who has given 500 presentations. He doesn't necessarily have some magical personality trait that you don't possess. He has 500 presentations worth of data. He knows what it feels like when the room goes quiet, to screw up a sentence, and to answer the questions people tend to ask. He knows that sometimes a presentation goes badly and... somehow... he survives.

You see the finished product and call him confident. He sees the accumulated evidence that got him there.

My First Attempt Wasn't Impressive

And I know this because I started with almost none.

The first time I seriously tried to approach a woman, I didn't walk confidently across the room, say something clever, and suddenly become the guy I wanted to be.

I was fucking terrified.

I remember finally getting close enough that I could actually say something. And I barely squeaked out a hello.

That's it.

Hello.

My heart was pounding. My brain was screaming at me to turn around. I didn't suddenly become confident because I had discovered some secret phrase or mastered women. I had simply finally taken one shot.

And when it was over, I had something I didn't have five minutes earlier: data.

I had approached a woman. I hadn't died. The world hadn't ended. I was actually proud of myself!

That tiny piece of evidence made the next attempt possible.

Over the next several years, I made thousands of approaches, screwed up more times than I could possibly remember, had conversations that went nowhere, had conversations that surprised me, and slowly accumulated enough experience that something that once felt almost impossible became something I could actually do.

I wrote the entire story down. Not because I think everyone needs to approach thousands of women, and not because I think approaching women is some magical solution to every problem in your life.

I wrote it because I know what it's like to spend years standing twenty feet away, wanting to do something and being completely unable to make yourself move. I know what it's like to know intellectually that something shouldn't be scary while your body is screaming at you that it is. And I know what it feels like when the first tiny crack finally appears in that wall.

If that's where you are right now, I wrote the story for you.

Read the story of how I broke through the wall.

READ THE FREE MEMOIR
← All Articles Next Article →