Hi guys.
First of all, I'm so glad I found this forum. I've been lurking around for quite some time, but now that I've started my journey to improve myself, I figured it was time to register and gain some friends here along the way

My background:
I'm a 23 year old man from Sweden, currently living in Japan. I'm blond, in shape and have a lot of friends. However, I've never been good with women. Or, I've always just become their friends, never getting any luck.
I believed coming to Japan would help, but even though I get a LOT of attention here, I still don't feel comfortable approaching women.

So! I decided two days ago to dedicate 30 days to improve my game. And it's been a blast! I still suck though, so I'd love to get some advice.

I've started using Neil Strauss' "Stylelife Challenge". So for the past two days I've been working getting comfortable talking with strangers. The first day I talked to 9 people, and even managed to Number Close a cute girl! (Yay!). Today I've talked to 5 people (going out for some more smalltalk leter), trying to connect with them more.
Even though I'm happy with the fact that it's getting easier to approach people, including women, I have this voice inside my head always telling me "What if she understands that I'm trying to pick her up?" "What if her boyfriend shows up?".
This voice is the reason why I struggle with going further than just asking directions etc.
How can I overcome this problem?

I approached a REALLY beautiful girl yesterday, something I would've NEVER dared if it wasn't for the fact that I'd been small talking with people all day, and to my big surprise she smiled and was very happy to talk to me. However, when I realized things actually might work and she might actually be interested in me, I freezed up, thanked her and walked away. The "What if she understands that I'm trying to pick her up?" "What if her boyfriend shows up?" questions came running back and I couldn't handle it.

What do you guys recommend me to do in order to actually get somewhere with all these approaches?
I really want to get better at day game, NOT night game. I just don't like the girls I see at clubs around here.
Improving my game here in Japan is hard - even though I speak Japanese fluently, I still struggle (especially when telling jokes etc), but I don't want to make any excuses. I want to get better now, and there's no day like today.

Thank you guys so much for your time.
I'm looking forward to getting to know you guys