For any young person it's important to know you can support yourself both financially and and socially. IMO it's important to live alone and not only get to know yourself but build that strength of knowing your own capabilities.
The basic idea of NaNoWriMo is that you write about 1667 words every single day for the entire month of November. If you do exactly that, you'll complete a short novel of 50,010 words by the end of the month.
There may be some blushing and stuttering but hey if you like the guy what have you got to lose? Guys, especially the ones dubbed the "nice guys", lack the ability to know whether you like them or not. Signals and flirting are difficult to read and understand. They need to be told in a straight forward way--not pushy or bitchy--always stay classy but don't be afraid to ask.