People often ask me, “How did you become comfortable approaching anyone?”
Today, I can start conversations with almost anyone—young or old, men or women, in Japan or abroad. It doesn’t matter if it’s on the street, at the beach, in a café, or even in a noisy club. But it wasn’t always like that.
Thirteen years ago, I was a shy IT engineer who had already been working for several years after graduate school—an ordinary guy living an ordinary life. Talking to strangers, especially attractive women, felt impossible.
The First Step
During a New Year’s break, I made a bold decision: I would start talking to people on the streets of Tokyo. I thought it would be easy. How hard could it be to just say hello?
It turned out to be harder than I imagined. For three days straight, I walked around for hours without saying a single word. My mind was filled with worry—“What if people stare? What if I embarrass myself?”
On the fourth day, I promised myself I would finally do it. My heart pounded, my palms sweated, and I whispered the quietest “Hello” of my life. The woman didn’t even hear me—but to me, it was a victory. That single moment of courage was the true beginning of my journey.
Small Wins, Big Lessons
By the fifth day, I was determined to have a real conversation. I’d bought a few learning materials—PDFs and audio programs that cost hundreds of dollars—because I was desperate to change. One of them included real conversation recordings, and I practiced by mimicking every phrase.
That night, I finally approached someone who responded. I copied a few lines from the program. She smiled, we talked briefly, and though she declined to give me her contact, I thanked her sincerely.
No number, no date—but huge progress. For the first time, I had connected with a stranger, shared a laugh, and proven to myself that it was possible.
The Breakthrough
The next day, I returned to the same district. For two hours, I hesitated again. I made excuses: “She’s probably busy.” “Now’s not the right time.” But then I saw her—a stylish woman walking alone, calm and confident.
I walked up and said, “Hi.” She smiled and asked me for directions. I helped her, added a bit of humor, and before she left, I took a deep breath and said, “Hey, can I get your number?”
She laughed and said, “Sure.”
I was stunned. After days of failure, one small moment changed everything. My heart was racing, and for the first time, I felt a rush of confidence.
I’d been proud before—getting into my dream university, landing my first job—but that simple moment of connection felt just as powerful, maybe even more. That was the day I realized this journey could truly change my life.
What Those Days Taught Me
Looking back, those awkward first attempts built the foundation for everything that came later. What started as a personal challenge eventually led me to travel the world, interview thousands of people, and build a community of nearly a million followers.
But more importantly, it taught me something simple yet life-changing: courage grows through repetition. The first step is always the hardest, but once you take it, every next step becomes easier.
You don’t have to be fearless. You just have to be willing.
If this story inspired you and you’d like to learn more about how to build confidence and connect with women naturally, I share free lessons and stories like this in my email series, The Global Attraction Blueprint. You can join here: The Global Attraction Blueprint.
