Bear is actually a lot older than he looks while in "The World".  He is always willing to help newbies out, and is a voice of reason for many of the main characters.

Not much is known about Bear in the real world, but what we do know is that he spends most of his time in "The World" and even has time enough to go searching for clues in the real world.  He is old enough to know and remember playing non-online RPGs, before "The World" was created.

He expresses his idea that "what if" games have their own realities.  Something that makes you think that the world the game takes place in is real somewhere and it has its own separate set of rules compared to the real world.  He expresses this even though he is grounded enough to know the reality of the situation.