Japanese Girl 1

How I Hooked up with a Japanese Girl in Tokyo as a Foreigner

I wanted to take 2 weeks off Singapore before University in Singapore resumes. Soon, the possibility of dating a Japanese girl got me on a one-way ticket towards Tokyo, Japan.

I choose Japan as I’ve never been there. It’s a country that I’ve always wanted to travel to but held back because of the high cost of living.

I also was stressed out building two projects, including this Singapore dating coach project over the last 3-4 months, and because of lackluster results, and I decided to buy myself a ticket to Japan, to recharge.

How I Met This Japanese Girl

I’ve been doing solo short trips ranging from 1 to 3 weeks to neighboring countries from Singapore for the past 4 years. Traveling solo is one of the toughest (yet most meaningful) pursuits in my life: the safety concerns, the periodical loneliness, and the self-reliance.

It’s lonely as fuck sometimes but at the same time, you’re putting yourself in a position where you are forced to take on new habits. You’re forced to be social. I notice a huge difference whenever traveling alone and when being back in Singapore. Back home, I live with my parents and having the comfort of home demotivates me at times to go out to socialize. However, if you’re in a new country alone, you pretty much don’t have a choice.

Normally, I would go landmark chasing when I’m in a new country. I would hit up Trip Advisor, search for the top 10 places to go to, and hit visit 3-4 landmarks within a day, hoping to cover them all during my short stay in a new country.

This time round, for Japan, I made it a point to NOT do that.

Landmarks are great, however, it gets meaningless after a certain point. I compare it to travel porn. It gets superficial and lacks depth and significance after a while.

I wanted to meet local Japanese people and soak into the traditional Japanese culture. And if I got lucky, I was hoping to meet a Japanese girl that likes me, and we can go to these landmarks and get food together.

Friends back in Singapore told me that 99% of the Japanese people here don’t speak English. I knew that the language barrier would be hard. But it’s still worth a try, human communication is once researched to be 70% non-verbal right?

Since this time I wasn’t going to go to landmarks after landmarks, and I’m not huge on chasing food restaurants after restaurants, I made it a point to meet new people.

I signed myself up for a Pub Crawl, an organized event where you got bar hopping with international friends.


From just one meetup event, I got to know a group of friends. I also I met a half Singaporean, half Swiss guy who I hit clubs with together. I ended up partying and having midnight sushi with a bunch of Japanese friends who have studied abroad during their University days.

That’s the power of people.

Instead of being alone, going to one restaurant and landmarks after another, I had a girl or others to show me around. Through her, I got to know more about Japanese culture.

Japanese Girl

The Japanese Streets

Dating a Half Japanese, Half Korean

I got to know a half Japanese, half Korean girl who studied abroad for a couple of years, grew up in Korea, and was working in Japan. She seemed pretty interested in me from the first time we met. I got her number and made plans.

The meet up wasn’t set up as a date and the intentions weren’t clear. I didn’t know if she was interested in me, or if she’s just being nice and showing this foreigner around in Tokyo. Being foreign to the country, she brought me around to sushi places, skyscrapers, and department stores. She showed me around Tokyo and brought me for good sushi and Japanese food.

When I first started out this dating advice thing, I used to obsess over the perfect date and pick up artist concepts such as “bouncing” on dates. However, throughout the recent years, I figured that a date should be enjoyable, and meaningful as well. I no longer buy into pick up artist concepts. I prefer to come from a more emotionally healthier perspective such as trust, leadership, and intimacy.

I got to know about her family and shared about mine. She came from a family that was divorced, and I related that I had a tough childhood growing up in a strict Singaporean family. We also connected on culture and travel. She mentioned she found it hard fitting into Japanese culture after leaving being influenced by Westernized ideals abroad.

I related by saying that Singaporean culture is something I’ve always ranted about through the years. She even shared that she dated a Singaporean guy a years ago and lamented the lack of expression in Singaporeans(or fucked up?). I agreed with her on that.

Singaporeans culture doesn’t promote the conversation about the things that should be talked about: sex, love, intimacy, trust and all of those important things. 

Pushing For Sex

On hindsight, I wasn’t leading physically much throughout the date. It’s one of my biggest “sticking points”. I found myself sitting back and chill, rather than being overly aggressive physically or for the kiss. I have to be more proactive, and not wait for the green lights.

We flirted a physically and she found herself holding on to my arm lightly. I hooked her hand around my bicep and we walked through the streets of Shinjuku.

I could tell she was interested and she was giving me hints of asking me if I was staying in an apartment by myself. (Just kind of confirms that girls are human beings and have needs too right?)

I don’t think pick up artist concepts and lines actually work on a superficial level to “seduce” a girl back to his. Terms such as “isolation”, “bouncing” and “pulling” are often thrown around in the industry. At the end of the day, it’s a painful and low-self esteem perspective. Most of the times, the girl is already interested in him, and the lines and concepts are just a backward rationalization and a vehicle to get them to the spot for sex.

Anyway, we went back to ours, and she asked:

“We’re not going to have sex are we?” – Her
“I want to, but if you’re not comfortable, that’s alright, we can just chill” – Me (and I fucking meant it)

That’s my game, literally. So much for “last minute resistance” uh?

Eventually, we did it, and it was good fun.

Lessons Learned Dating a Japanese Girl

Dating a Japanese Girl

I got lost in one of their Subways.

It got me thinking of quality of interactions and really pushing you to go for the girl that you really like. Failing on a date with a girl that makes you really excited is much better than going on a date that makes you feel like “meh”.

Having dates, and “notches” is one thing. Having the quality of interactions is another. If I was being brutally fucking honest, I slept with her, because it was easy. I was actually into one of her friends, and I wasn’t that attracted to her.

I started this pick up artist journey when I was 19 and would hit on any girl that fulfills society’s standards of beauty. For some reason, it felt that I “had” to do it because if I didn’t, that would be I am a failure as a “self-development”, “pick up artist” or “self-improvement” guy.

Looking back, there were girls that I shouldn’t have went for and girls that I definitely should have gone for.

It also got me thinking about long term relationships, love, and intimacy. Having sex is great, but it gets boring and repetitive after awhile.

Hence it’s important to find someone you find really sexually attractive and not just physically attractive. Having sex for the sake of having sex,  fulfilling the ‘player’ or ‘casanova’ identify that is pointless.

Pick up artists find themselves hitting on girls that they are not emotionally or sexually attracted to, but to just fulfill this identity they’ve built for themselves over the years. I personally feel like that at this point in my life.

Hence it’s so important to dig deep into our emotional truths, that’s the only way out. What am I avoiding? What’s fucking me up deep down inside that led to these behaviors?

How can I still feel so empty inside?

No Longer Identifying with The Highs and the Lows

I remembered missing my flight in Japan. Despite accomplishing my goals: dating a Japanese girl, and an overall positive trip in Japan, I felt empty.

I also hated the fact that I had to find a new friend daily or bore myself in the hotel. I hated the fact that I had to go to somewhere new every day, or bore myself staring into my computer. I was spending away from my savings, getting nowhere with my travels. Perhaps I would have written differently if I had a steady stream of income.

Short term dating is fun. The sex is fun. The novelty is fun. However, I think that there are upsides to a long term relationship than a short term. There are things that can be experienced in a long term relationship than a short term one.

I made a decision at the airport airport.

I was going to go back to Singapore, built my business, attend school, and be ‘normal’.

Being special isn’t so special after all.

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  • Benjamin

    Hey man, i found your blog today and i find your content interesting. I find myself having the same dilemmas as you and it’s great to find someone with the same mindset/problems. i am 21 years old and soon to be university student as well. Care to chat more?