DW and I believe our job as parents is to prepare our children for a life without us. In today's overly protective society this makes us pretty radical, even in our homeschooling group. We've been a long-time follower of the free range kid ideology.

It hard to find the right balance. We want our daughters to be confident enough in themselves to not be afraid to speak to strangers yet aware enough to keep an eye out for dangers. Their basic mantra if they feel uncomfortable with someone or something is:
1. Stop
2. Get Away (by ANY means necessary)
3. Tell Someone (us, a policeman, another one of the moms in the group)

I make it a point to talk to strangers in the presence of my kids so they can see that doing so isn't a bad thing, that there's nothing wrong with chatting with the person waiting in line with you, at the neighborhood pool, dangling upsidedown from a bridge, etc... When we go out to places the DDs are responsible for ordering their own food and dealing with shopkeepers/ticket venders/performers or whoever else an adult would normally deal with.

We let them walk the two blocks to their friend's house without adults (which drives their friend's mom nuts) and they don't have to be in the same asile as us (as long as they are behaving!) at the grocery store (though we don't let them get farther away than the next asile). On our nightly walks they are usually a block or more ahead of me.

It's really not easy. There are times when I have to repeat to myself "it's okay, they'll be safe" because the odds are they will be by a very very long shot. I feel the large benefits outweigh these risks.

-Blast