More or less start somewhere. There may be a chronological order (in the heresy) but after that it’s more of a suggestion. Pick a faction or topic you like and go from there.

I found my GF as the new roommate of my more extroverted friend…

You don’t need to speak to people on the street. Some contact to new people would probably help. This can be done trough (more) extroverted friends of you. But it will require effort from you to be open to new people.

Real question how du I make it classy

Point still stands