We went to the park on Monday with some friends and after 30+minutes of observing and sitting/standing COMPLETELY still (I mean still, like a statue) he starting wandering around. Every time we go somewhere new or to a playdate he just watches everything at the beginning and doesn't play with anyone. Then he gets up the courage and he is off! He goes off and plays by himself or with other kids and no need for Mama anymore!
He also walked around the park and on concrete for the first time. Mama was a nervous wreck since he hadn't really been outside yet as a "walker". He did great and really had a lot of fun! I think he was awfully proud of himself too!