How do you decide when a new person is safe enough to see your anxious side?

What's something you used to be afraid of that you now find easy, and what actually got you past it?
What public places are best for starting a conversation with a stranger?
Where do we go after our only refuge (the internet) is destroyed completely? What do we do?
Why do people sometimes choose to protect themselves emotionally rather than pursue a relationship with a difficult family member?