How to build the courage to express desire
The practice of taking initiative with women and owning your space in the world
Most men have a feeling deeply rooted inside them. Unless you were the kind of man who was always picked and given attention by attractive women from a young age, you know it well.
I have done many things that people consider scary. I have traveled the world alone, tried skydiving, taken psychedelic trips, and changed careers several times. Yet approaching a woman I am attracted to still feels more frightening than all of that.
In the previous article, I covered why you need to learn how to walk away. We looked at why rejection is usually just a reaction to a moment, rather than a verdict on your worth.
Once you know you can leave an interaction at any time, the stakes change. You aren’t acting like your life depends on it anymore; you are just having a conversation.
Now we can move to the next part. You’ve lowered the risk. Now it is time to look at why you have been holding back, and how to start moving forward.
What boldness looks like with women
We often confuse boldness with aggression or some kind of forced performance. It is neither of those. With women, boldness means saying what you want or what you feel, even when you are not sure how it will come across.
You need boldness the moment you sense a gap between what you want and how you are acting. If you are attracted to someone but you act like a friend or a bystander, you are choosing safety over honesty.
A “safe” man hides his interest because he is afraid of being judged. A bold man treats his interest as a normal, human thing to express. He doesn’t need to be loud or arrogant; he just needs to be transparent.
Women are often waiting for someone to take the first step. Without your boldness, the moment often just passes.
Why do we struggle to be bold?
To understand why you freeze, you have to look at the two forces working against you. One is the deep and biological past you cannot change, and the other is the social conditioning you can choose to ignore.
The survival instinct
Our brains developed in small tribes where your place in the group could mean survival. If you were rejected by the tribe or embarrassed yourself in front of the wrong person, you risked being pushed out. In those conditions, being alone often meant you would not survive or find a mate to reproduce.
Even though we now live in cities full of strangers we will never see again, our brains still treat a simple conversation like a life-threatening risk. This is the hardware you were born with. Do not expect that to change in your lifetime. You have to learn to act while your brain is still telling you that you are in danger.
The good boy conditioning
Society built on top of that fear by teaching us to be “good.” We were raised to follow rules, be polite, and wait our turn. This works well in a classroom, but it is a disaster for your dating life. It creates a habit of waiting to be “picked” instead of being the one who chooses. You end up feeling that your desire is something you are imposing on a woman.
You worry that you are bothering her, so you stay quiet and wait for a clear sign that rarely comes.
The creep paradox
This has created a modern mess. Many men fear that their sexual or romantic interest is toxic. Because you want to be respectful, you over-correct. You confuse harassment with simple desire.
Harassment is about ignoring boundaries and making someone feel unsafe. A respectful compliment or an invitation to talk is a gift, not a crime.
Boldness requires realizing that showing your interest (as long as you are respectful and you know how to walk away) is a compliment.
How to be creepy
Most men are so afraid of being “creepy” that they do nothing at all. They think that simply having a romantic interest makes them look like a creep.
To stop worrying about this, you need to understand what actually makes a man creepy. It is not about your looks or your nervousness. It is about not paying attention to the signals the other person gives you.
If you want to be truly creepy, here is how:
Be attached to the outcome: Decide that you must get her number or you have failed. This makes the woman feel like a prize to be won, not a person to be met.
Ignore her social cues: If she is looking at her phone, turning her body away, or giving one-word answers, keep talking anyway.
Make her feel watched: Stare at her from across the room without a smile or movement. Follow her when she moves to another area.
Invade her space: Stand too close, block her exit, or touch her before there is any mutual comfort.
Refuse to leave: When the conversation is clearly over, stay there and wait for her to give you what you want.
If you are reading this, you probably do not do these things. You are a respectful man. To not be creepy, all you have to do is offer an invitation and be ready to let go of the result.
As long as you respect her space and can take a “no” without getting upset, you are not being creepy. You are just being a man who goes for what he wants.
The solution
Avoiding the “creep” label is just a matter of respecting boundaries. But to actually build boldness, you need to change your focus. Instead of trying to earn her validation, start evaluating if she is someone you even want in your life.
Take her off the pedestal
In reality, she is just a messy human like you. She has insecurities and nightmares. She wants to be comforted. She feels lonely on Friday nights. And she is probably better than you at hiding what she wants.
While you might feel judged based on your height or your status, she feels judged based on her looks. She is dealing with her own pressure and her own struggles.
Move from performing to filtering
Most men approach an interaction by trying to entertain, impress, or “win” the woman. They treat the conversation like an audition where they have to prove their worth. That is the quickest way to feel heavy and needy. Instead, start filtering.
You are an evaluator. You aren’t there to convince her that you are a catch; you are there to see if she is someone you actually want in your life.
If you don’t know your own values or what kind of dynamic you want, you will simply react to beauty and chase anyone who is attractive and available. Do the work to figure out what you want. When you know your own standards, you stop trying to “get” her and start seeing if she meets your criteria.
The courage to be disliked
If you try to be inoffensive to everyone, you become invisible. You end up being so “nice” that you are boring.
Here’s one of my favourite quote:
“You can be the ripest, juiciest peach in the world, and there is still going to be somebody who hates peaches.”
If you are not occasionally disliked, it means you are being too generic. Showing your real personality and your real opinions might lead to a quicker “no,” but it is the only way to find a real connection.
How to build boldness
Reading about this does not change your behavior. You have to put yourself in situations where you feel the hesitation and move anyway. You have to start where you are.
The habit of being social
The best way to lower the pressure is to make talking to strangers a normal part of your day. If you only talk to women you are attracted to, you make every interaction feel like a big deal.
Start talking to everyone. Talk to the older man in line at the coffee shop. Talk to the cashier. Be curious in your interactions and make small talk with people you are not attracted to. When you do this, you train your brain to realize that talking to people is a neutral activity.
You aren’t “hitting on” anyone. You are just being the kind of man who is present and social in the world. Once you get used to that, approaching the woman you find attractive (almost) becomes just another chat.
Reframing the physical nerves
When you feel the pull to talk to a woman, your body will react. Your heart will race, your voice might tighten, and you might get a bit of tunnel vision. Most men take this as a stop sign. They assume that if they feel scared, they must be doing something wrong.
Do not look at it that way. That physical reaction is just raw energy. It is your system getting ready to act. Think of it like a professional athlete standing in the starting blocks. They are not scared, but their body is completely alert and ready to go.
When you feel that tightness, don’t try to calm down. Instead, take a deep breath to maintain control, and use that energy to move toward her. Speak slowly and clearly. If you talk fast, you signal that you are anxious. If you talk slowly, you signal that you are in control of the situation.
Microdosing risk
Once you are comfortable with small talk, take the next step that feels slightly uncomfortable. If you are paralyzed by the idea of saying hi to a woman you like, start with the absolute minimum. Ask a stranger for directions to a nearby street.
When that feels easy, try a light compliment. If you are at a cafe, tell a woman you like her scarf or her coat, and then turn back to your book or walk away. You are practicing the act of expressing a preference without needing a result.
Do this over and over. By keeping the interaction short, you prove to your brain that the world does not end when you speak your mind. You are training yourself to act even when that resistance shows up.
There are no scripts
You don’t need to memorize lines. In fact, if you try to use a scripted approach, you will sound like you are acting. The best approach is one that feels like a normal social interaction. That’s why practising small daily chit-chats with strangers is so valuable.
People expect a level of politeness and directness when a stranger walks up to say hello. By following a standard and respectful flow, you avoid any surprises and let the other person know you are safe.
For example, I often hold eye contact with a woman I am attracted to for a few seconds. If she holds the eye contact, I wait for a natural moment and walk over.
I might say something like:
“Sorry I have been staring. I just noticed you have very expressive and vibrant eyes.”
That is it. Depending on the vibe and how she receives it, I might follow up with a simple question, like asking if she is a regular at this spot. But the words themselves do not matter as much as you think. Their only purpose is to keep the conversation moving and give her space to respond. This is how you find out if she is interested in continuing the conversation, and as importantly, if you want to continue it yourself.
I always remind myself that me approaching her does not mean anything yet. It does not mean I am planning a future, and it certainly does not mean I want to date her. It simply means I saw someone I was curious about, and I had the courage to express myself in the moment.
Talking to someone is not a contract. It is just a conversation. If it goes well, you keep talking. If it does not, you have already practiced the art of walking away.
The practice goes beyond dating
This boldness practice does not stop with women. If you are mindful, the same boldness you build in the café will start to show up in every other part of your life.
You learn to own your space. Every time you speak up when you would rather stay quiet, you send a signal to yourself. You are telling your brain that you are a man who does not back away when the situation feels difficult.
You get better at keeping your boundaries. If you can handle a “no” from a stranger without falling apart, you can handle a “no” from a client, a manager, or a friend who asks too much of you. You stop being the “good boy” who goes along with everything and start being the man who knows his limits.
You build the capacity to protect. If you are afraid to speak up for yourself, you will not be able to stand up for others. By practicing small acts of boldness, you learn to step in when someone else is being treated unfairly. You learn to hold your ground for your own values and for the people who count on you.
You stop performing. A man who is bold with women but stays silent when his boss insults him is not actually bold. He is just performing. Real boldness is a consistent practice. It stays with you regardless of who you are talking to.