I've actually had some success on the shyness front. I did two things here: took a course on improvisational comedy, and hung out with some pick-up artists who showed me how they start conversations with women. These things got me into the mindset of "when something looks like I couldn't possibly do it, test that hypothesis." Last Saturday, I actually got a date by walking up to a woman on the street and asking her! Later that night, I had dinner with her and her family. Even a year ago, this would have been unthinkable.

Well done - that's impressive.