My 20-week old has exhibited this behavior since he was 10-weeks old. He'll do this in his own backyard or out on walks --

He'll hear a dog barking the next yard over and then make a mad dash to me. He puts himself behind me or if I'm sitting somewhere, he'll move between my legs, sometimes backing in so he's seated upright with his body firmly situated between my knees. Every so often, he'll lay between my feet. In each instance he's always looking out and forward. He'll usually drop his head while he makes his way to me and his tail is set low (but not between his legs). Once he's set up his position, he's quiet but alert with his head high.

At first I found the behavior endearing when he was much smaller. I still do but I don't want to further set him up for confidence issues if that's what I'm doing? I probably have already done that since I admit I coddled him in a protective way when he did this.

He's a bold guy otherwise and has not been fearful or timid of new sounds or situations.

I just ordered "Your Puppy 8 Weeks to 8 Months," "Basic Dog Obedience," "Establishing Pack Structure" and "Building Drive & Focus." Whew. I'm not sure if this type of behavior is brought up in any of those DVD's.

If I need to address this, how should I do it?

Ignore him. Keep your legs closed so he can't squeeze between them. Calling attention to a behavior makes it worse.