I only have Loki, so I won't comment on the issues with 2 dogs, although a good friend of mine does walk her dogs separately but I don't know if they have separation anxiety. If so, Kongs work great for that.
Anyway, for the nervous one, some positive reinforcement training would work wonders. Loki gets nervous around big dogs too. What they trainer has us do is have Loki sit to the side of the path when another dog walks by. I keep his attention with treats and reward him for not barking (he likes to let the big dogs know he's tough). He is learning that 1 - I will protect him and 2 - big dogs = yummy treats. There are so many other things we have worked on in classes that help too - like the "watch" command so that he looks up at me rather than the distraction. There are so many things you can do with positive reinforcement to help a shy dog. If you can sign up for a class I would highly suggest it. Otherwise, check to see if your library has any books by Pat Miller or Patricia McConnell. Amazon has them if your library does not. There are many other books I can recommend if you are interested in learning more. There are so many ways to make your shy one more confident.
Also, Loki has wanted to stop more lately, as it gets nice out and things are growing and smell good. He has done classes forever and knows lots of commands, like watch and come. We just use those to get his attention and he follows. We have also worked quite a bit on loose leash walking - very helpful! I use an Easy Walk harness on him, which discourages pulling without hurting him. He is capable of walking nicely on a collar, but if he ever does pull too hard this harness does not choke him. We stop 2-3 times on our walks. I choose times when he is behaving/not pulling and reward him by letting him sniff a little. |