Chapter 1: Confronting Approach Anxiety

In 2016, I embarked on a personal challenge to conquer my fear of approaching women. Over the course of 50 days, I made it a goal to engage with two attractive women daily. I won't sugarcoat it; it was intimidating and perhaps one of the most challenging undertakings I’ve ever faced. Each day, I felt the weight of anxiety as I prepared to approach new individuals. There were numerous moments when I wanted to give up, and I often regretted starting this endeavor. To add to the pressure, I documented my experiences publicly on Facebook and Reddit, which only heightened my sense of vulnerability.

However, looking back, that period is now behind me. The time I devoted to confronting my fears has equipped me with the confidence to approach women anywhere, a skill I truly value. This experience taught me that time is fluid and what feels permanent is often temporary. It also made me ponder a crucial question: would I prefer the fleeting discomfort of change or the lasting pain of stagnation? #youdecide

Now, let's dive back into the challenge.

Encounter 1: Beko

So today, while traveling, I noticed a stunning Japanese businesswoman named Beko. She was immersed in her music, and I learned she had recently moved from Tokyo to London. Initially, I hesitated to approach her, but then I realized that avoiding interaction was not an option. I walked over, complimented her appearance, and we struck up a conversation.

Interestingly, it seems that men in Japan typically don't introduce themselves to strangers. Beko appeared a bit anxious, so I made sure to maintain a comfortable distance while we talked. I even tossed in a few Japanese phrases I knew, which made her giggle. Beko mentioned she was on her way to meet a friend and wasn't comfortable exchanging contact information, but she was open to taking a selfie together. After snapping a quick picture, I wished her well and moved on.

Encounter 2: A Stranger

Next, I approached a woman who had a Latin appearance and was seated a few chairs away from me in Starbucks. After mustering my courage for a brief moment in the quiet yet crowded café, I finally went over to say hello. Unfortunately, she had just come from a terrible interview and needed some time to herself.

Drawing from my own experiences with interviews, I shared a technique that has helped me: spend some time beforehand building your confidence. Half of your success hinges on how you present yourself, which is largely influenced by your self-assurance. I encouraged her to view each interview as just one opportunity and not let a single setback define her.

She appreciated the advice but seemed determined to dwell in her disappointment, so I returned to my seat, feeling like a playful bunny.

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Reflections

Lately, I’ve experienced some exciting developments as a result of this challenge. I have received numerous messages from men inspired by my journey, which is truly rewarding. Additionally, I've been invited to participate in a podcast interview, which is fantastic news. A gentleman from India even reached out, asking if I’d be willing to travel there to teach men how to approach women—what an unexpected honor!

These interactions indicate that my challenge is garnering attention, which adds a layer of pressure. Knowing that people are watching makes me anxious about the possibility of disappointing them. As a result, I feel compelled to come up with more creative approaches to keep things interesting, or even exaggerate my successes to maintain a favorable image.

Nevertheless, I promise to remain authentic throughout this journey. Even if no one else knows the truth, I will, and I refuse to misrepresent myself.

Just moments after I penned those thoughts, I noticed a woman sitting across from me and introduced myself—not out of obligation, but because I knew I would regret it otherwise. After complimenting her stunning figure, she playfully expressed disbelief that I was addressing her. We ended up having a delightful conversation. Her name is Kim, she hails from Thailand, and she’s working on a dissertation about organic food. We agreed to meet for drinks tomorrow.

Step outside your comfort zone, my friends. Ciaran encourages it. Kim does too.

14 days down, 36 to go.

Read about day 15 of my journey with 100 Women in 50 Days below.

100 Women in 50 Days

In 2016, I undertook a challenge to conquer my fear of approaching beautiful women. This is the complete account of that journey.

Don’t Let Fear Control You: A Surprising Encounter with Kaylah

I was just as astonished as you might be.

If you enjoyed this, download my free ebook, "How to Approach Women," for more motivational insights.

Chapter 2: Realities of Dating as a Black Man in Japan

Exploring the experiences of Black men in Japan, this video delves into the unique challenges and perspectives they face in the dating scene.

This video uncovers the truth about dating as a Black individual in Japan, shedding light on personal stories and insights from the Black community.