Freedom of Speech, Thought, and Expression

Where does liberty originate? The founders stated that our basic liberties are endowed upon all human beings by a creator, some would say G(g)od. Others argue that liberties and freedoms are culturally agreed upon, even if implicitly. A third view suggests that rights and freedoms are bestowed upon constituents by governments or rulers.
What are the extents of human liberties? At what point do we say a person's liberty must be usurped? Traditionally, the limits of personal liberty has been expressed by statements such as "one person's liberty ends where another person's liberty begins. In other words, my liberty cannot interfere with or counteract your liberty. But what if I exercise my liberties against what you think I should do? Do I have the freedom to choose to be poor? Do I have the freedom to choose not to get medical care or medical insurance? Do you have the freedom to be a racist as long as you do no harm to people of other races? Do we have the right to live an unhealthy lifestyle? Do we have the freedom to marry whomever we choose? Do we? Should we? Dare we?